Draw structures corresponding to the following names: (a) 3, 3-Dimethyl-4-octyne (b) 3-Ethyl-5-methyl-1, 6, 8-decatriyne (c) 2, 2, 5, 5-Tetramethyl-3-hexyne (d) 3, 4-Dimethylcyclodecyne (e) 3, 5-Heptadien-1-yne (f) 3-Chloro-4, 4-dimethyl-1-nonen-6-yne (g) 3- sec -Butyl-1-heptyne (h) 5- tert -Buty1-2-methyl-3-octyne

Question

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Answer 1

Textbook Question

Chapter 9.SE, Problem 27AP

Draw structures corresponding to the following names:

(a) 3, 3-Dimethyl-4-octyne

(b) 3-Ethyl-5-methyl-1, 6, 8-decatriyne

(c) 2, 2, 5, 5-Tetramethyl-3-hexyne

(d) 3, 4-Dimethylcyclodecyne

(e) 3, 5-Heptadien-1-yne

(f) 3-Chloro-4, 4-dimethyl-1-nonen-6-yne

(g) 3-sec-Butyl-1-heptyne

(h) 5-tert-Buty1-2-methyl-3-octyne

Expert Solution

Interpretation Introduction

a) 3,3-Dimethyl-4-octyne.

Interpretation:

The structure of 3,3-Dimethyl-4-octyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 3,3-dimethyl-4-octyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3,3-dimethyl-4-octyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 1

Explanation of Solution

The name shows that the longest carbon chain should contain eight carbons with a triple bond between C₄ & C₅ and two methyl groups should be present on C₃.

Conclusion

The structure corresponding to the IUPAC name 3,3-dimethyl-4-octyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 2

Expert Solution

Interpretation Introduction

b) 3-Ethyl-5-methyl-1,6,8-decatriyne.

Interpretation:

The structure of 3-ethyl-5-methyl-1,6,8-decatriyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 3-ethyl-5-methyl-1,6,8-decatriyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3-ethyl-5-methyl-1,6,8-decatriyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 3

Explanation of Solution

The name shows that the longest carbon chain should contain ten carbons with three triple bonds, one between C₁ & C₂, another between C₆ & C₇ a third one between C₈ & C₉, an ethyl group on C₃ and a methyl group on C₅.

Conclusion

The structure corresponding to the IUPAC name 3-ethyl-5-methyl-1,6,8-decatriyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 4

Expert Solution

Interpretation Introduction

c) 2,2,5,5- tetramethyl-3-hexyne.

Interpretation:

The structure of 2,2,5,5- tetramethyl-3-hexyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 2,2,5,5- tetramethyl-3-hexyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 2,2,5,5- tetramethyl-3-hexyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 5

Explanation of Solution

The name shows that the longest carbon chain should contain six carbons with a triple bond between C₃ & C₄ and four methyl groups, two on C₂ and another two on C₅.

Conclusion

The structure corresponding to the IUPAC name 2,2,5,5- tetramethyl-3-hexyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 6

Expert Solution

Interpretation Introduction

d) 3,4-Dimethylcyclodeceyne.

Interpretation:

The structure of 3,4-Dimethylcyclodeceyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 3,4-dimethyl cyclodeceyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3,4-dimethyl cyclodeceyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 7

Explanation of Solution

The name shows that the compound contains a ring made up of ten carbon atoms with a triple bond attached to two methyl groups on C₃ and C₄.

Conclusion

The structure corresponding to the IUPAC name 3,4-dimethyl cyclodeceyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 8

Expert Solution

Interpretation Introduction

e) 3,5-Heptadiene-1-yne.

Interpretation:

The structure of 3,5-heptadiene-1-yne is to be drawn.

Concept introduction:

The longest carbon chain which contains the carbon-carbon triple bond is chosen. The chain is numbered from the end that gives the lowest number to the carbon in triple bond. Compounds with more than one triple bond are called diynes, triynes and so forth. Compounds containing both double bond and triple bonds are called as enynes. The chain is numbered from the end nearer to the multiple bonds, double or triple. When there is a choice in numbering the double bond is given preference and the lowest number is assigned to it.

To draw:

The structure corresponding to the IUPAC name 3,5-heptadiene-1-yne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3,5-heptadiene-1-yne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 9

Explanation of Solution

The name shows that the longest carbon chain should contain seven carbons with a triple bond between C₁ & C₂ and two double bonds, one between C₃ & C₄ and another between C₅ & C₆.

Conclusion

The structure corresponding to the IUPAC name 3,5-heptadiene-1-yne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 10

Expert Solution

Interpretation Introduction

f) 3-Chloro-4,4-dimethyl-1-nonene-6-yne.

Interpretation:

The structure of 3-chloro-4,4-dimethyl-1-nonene-6-yne is to be drawn.

Concept introduction:

The longest carbon chain which contains the carbon-carbon triple bond is chosen. The chain is numbered from the end that gives the lowest number to the carbon in triple bond. Compounds with more than one triple bond are called diynes, triynes and so forth. Compounds containing both double bond and triple bonds are called as enynes. The chain is numbered from the end nearer to the multiple bonds, double or triple. When there is a choice in numbering the double bond is given preference and the lowest number is assigned to it.

To draw:

The structure corresponding to the IUPAC name 3-chloro-4,4-dimethyl-1-nonene-6-yne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3-chloro-4,4-dimethyl-1-nonene-6-yne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 11

Explanation of Solution

The name shows that the longest carbon chain should contain nine carbons with a triple bond between C₆ & C₇, one double bond between C₁ & C₂, a chlorine atom on C₃ and two methyl groups on C₄.

Conclusion

The structure corresponding to the IUPAC name 3-chloro-4,4-dimethyl-1-nonene-6-yne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 12

Expert Solution

Interpretation Introduction

g) 3-sec-Butyl-1-heptyne.

Interpretation:

The structure of 3-sec-Butyl-1-heptyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 3-sec-butyl-1-heptyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3-sec-butyl-1-heptyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 13

Explanation of Solution

The name shows that the longest carbon chain should contain seven carbons with a triple bond between C₁ & C₂ and a sec-butyl group on C₃.

Conclusion

The structure corresponding to the IUPAC name 3-sec-butyl-1-heptyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 14

Expert Solution

Interpretation Introduction

h) 5-tert-Butyl-2-methyl-3-octyne.

Interpretation:

The structure of 5-tert-Butyl-2-methyl-3-octyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 5-tert-Butyl-2-methyl-3-octyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 5-tert-Butyl-2-methyl-3-octyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 15

Explanation of Solution

The name shows that the longest carbon chain should contain eight carbons with a triple bond between C₃ & C₄, a tert-butyl group on C₅ and a methyl group on C₂.

Conclusion

The structure corresponding to the IUPAC name 5-tert-Butyl-2-methyl-3-octyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 16

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Answer 2

Textbook Question

Chapter 9.SE, Problem 27AP

Draw structures corresponding to the following names:

(a) 3, 3-Dimethyl-4-octyne

(b) 3-Ethyl-5-methyl-1, 6, 8-decatriyne

(c) 2, 2, 5, 5-Tetramethyl-3-hexyne

(d) 3, 4-Dimethylcyclodecyne

(e) 3, 5-Heptadien-1-yne

(f) 3-Chloro-4, 4-dimethyl-1-nonen-6-yne

(g) 3-sec-Butyl-1-heptyne

(h) 5-tert-Buty1-2-methyl-3-octyne

Expert Solution

Interpretation Introduction

a) 3,3-Dimethyl-4-octyne.

Interpretation:

The structure of 3,3-Dimethyl-4-octyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 3,3-dimethyl-4-octyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3,3-dimethyl-4-octyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 1

Explanation of Solution

The name shows that the longest carbon chain should contain eight carbons with a triple bond between C₄ & C₅ and two methyl groups should be present on C₃.

Conclusion

The structure corresponding to the IUPAC name 3,3-dimethyl-4-octyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 2

Expert Solution

Interpretation Introduction

b) 3-Ethyl-5-methyl-1,6,8-decatriyne.

Interpretation:

The structure of 3-ethyl-5-methyl-1,6,8-decatriyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 3-ethyl-5-methyl-1,6,8-decatriyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3-ethyl-5-methyl-1,6,8-decatriyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 3

Explanation of Solution

The name shows that the longest carbon chain should contain ten carbons with three triple bonds, one between C₁ & C₂, another between C₆ & C₇ a third one between C₈ & C₉, an ethyl group on C₃ and a methyl group on C₅.

Conclusion

The structure corresponding to the IUPAC name 3-ethyl-5-methyl-1,6,8-decatriyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 4

Expert Solution

Interpretation Introduction

c) 2,2,5,5- tetramethyl-3-hexyne.

Interpretation:

The structure of 2,2,5,5- tetramethyl-3-hexyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 2,2,5,5- tetramethyl-3-hexyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 2,2,5,5- tetramethyl-3-hexyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 5

Explanation of Solution

The name shows that the longest carbon chain should contain six carbons with a triple bond between C₃ & C₄ and four methyl groups, two on C₂ and another two on C₅.

Conclusion

The structure corresponding to the IUPAC name 2,2,5,5- tetramethyl-3-hexyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 6

Expert Solution

Interpretation Introduction

d) 3,4-Dimethylcyclodeceyne.

Interpretation:

The structure of 3,4-Dimethylcyclodeceyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 3,4-dimethyl cyclodeceyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3,4-dimethyl cyclodeceyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 7

Explanation of Solution

The name shows that the compound contains a ring made up of ten carbon atoms with a triple bond attached to two methyl groups on C₃ and C₄.

Conclusion

The structure corresponding to the IUPAC name 3,4-dimethyl cyclodeceyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 8

Expert Solution

Interpretation Introduction

e) 3,5-Heptadiene-1-yne.

Interpretation:

The structure of 3,5-heptadiene-1-yne is to be drawn.

Concept introduction:

The longest carbon chain which contains the carbon-carbon triple bond is chosen. The chain is numbered from the end that gives the lowest number to the carbon in triple bond. Compounds with more than one triple bond are called diynes, triynes and so forth. Compounds containing both double bond and triple bonds are called as enynes. The chain is numbered from the end nearer to the multiple bonds, double or triple. When there is a choice in numbering the double bond is given preference and the lowest number is assigned to it.

To draw:

The structure corresponding to the IUPAC name 3,5-heptadiene-1-yne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3,5-heptadiene-1-yne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 9

Explanation of Solution

The name shows that the longest carbon chain should contain seven carbons with a triple bond between C₁ & C₂ and two double bonds, one between C₃ & C₄ and another between C₅ & C₆.

Conclusion

The structure corresponding to the IUPAC name 3,5-heptadiene-1-yne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 10

Expert Solution

Interpretation Introduction

f) 3-Chloro-4,4-dimethyl-1-nonene-6-yne.

Interpretation:

The structure of 3-chloro-4,4-dimethyl-1-nonene-6-yne is to be drawn.

Concept introduction:

The longest carbon chain which contains the carbon-carbon triple bond is chosen. The chain is numbered from the end that gives the lowest number to the carbon in triple bond. Compounds with more than one triple bond are called diynes, triynes and so forth. Compounds containing both double bond and triple bonds are called as enynes. The chain is numbered from the end nearer to the multiple bonds, double or triple. When there is a choice in numbering the double bond is given preference and the lowest number is assigned to it.

To draw:

The structure corresponding to the IUPAC name 3-chloro-4,4-dimethyl-1-nonene-6-yne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3-chloro-4,4-dimethyl-1-nonene-6-yne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 11

Explanation of Solution

The name shows that the longest carbon chain should contain nine carbons with a triple bond between C₆ & C₇, one double bond between C₁ & C₂, a chlorine atom on C₃ and two methyl groups on C₄.

Conclusion

The structure corresponding to the IUPAC name 3-chloro-4,4-dimethyl-1-nonene-6-yne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 12

Expert Solution

Interpretation Introduction

g) 3-sec-Butyl-1-heptyne.

Interpretation:

The structure of 3-sec-Butyl-1-heptyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 3-sec-butyl-1-heptyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3-sec-butyl-1-heptyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 13

Explanation of Solution

The name shows that the longest carbon chain should contain seven carbons with a triple bond between C₁ & C₂ and a sec-butyl group on C₃.

Conclusion

The structure corresponding to the IUPAC name 3-sec-butyl-1-heptyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 14

Expert Solution

Interpretation Introduction

h) 5-tert-Butyl-2-methyl-3-octyne.

Interpretation:

The structure of 5-tert-Butyl-2-methyl-3-octyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 5-tert-Butyl-2-methyl-3-octyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 5-tert-Butyl-2-methyl-3-octyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 15

Explanation of Solution

The name shows that the longest carbon chain should contain eight carbons with a triple bond between C₃ & C₄, a tert-butyl group on C₅ and a methyl group on C₂.

Conclusion

The structure corresponding to the IUPAC name 5-tert-Butyl-2-methyl-3-octyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 16

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Answer 3

Textbook Question

Chapter 9.SE, Problem 27AP

Draw structures corresponding to the following names:

(a) 3, 3-Dimethyl-4-octyne

(b) 3-Ethyl-5-methyl-1, 6, 8-decatriyne

(c) 2, 2, 5, 5-Tetramethyl-3-hexyne

(d) 3, 4-Dimethylcyclodecyne

(e) 3, 5-Heptadien-1-yne

(f) 3-Chloro-4, 4-dimethyl-1-nonen-6-yne

(g) 3-sec-Butyl-1-heptyne

(h) 5-tert-Buty1-2-methyl-3-octyne

Expert Solution

Interpretation Introduction

a) 3,3-Dimethyl-4-octyne.

Interpretation:

The structure of 3,3-Dimethyl-4-octyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 3,3-dimethyl-4-octyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3,3-dimethyl-4-octyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 1

Explanation of Solution

The name shows that the longest carbon chain should contain eight carbons with a triple bond between C₄ & C₅ and two methyl groups should be present on C₃.

Conclusion

The structure corresponding to the IUPAC name 3,3-dimethyl-4-octyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 2

Expert Solution

Interpretation Introduction

b) 3-Ethyl-5-methyl-1,6,8-decatriyne.

Interpretation:

The structure of 3-ethyl-5-methyl-1,6,8-decatriyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 3-ethyl-5-methyl-1,6,8-decatriyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3-ethyl-5-methyl-1,6,8-decatriyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 3

Explanation of Solution

The name shows that the longest carbon chain should contain ten carbons with three triple bonds, one between C₁ & C₂, another between C₆ & C₇ a third one between C₈ & C₉, an ethyl group on C₃ and a methyl group on C₅.

Conclusion

The structure corresponding to the IUPAC name 3-ethyl-5-methyl-1,6,8-decatriyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 4

Expert Solution

Interpretation Introduction

c) 2,2,5,5- tetramethyl-3-hexyne.

Interpretation:

The structure of 2,2,5,5- tetramethyl-3-hexyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 2,2,5,5- tetramethyl-3-hexyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 2,2,5,5- tetramethyl-3-hexyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 5

Explanation of Solution

The name shows that the longest carbon chain should contain six carbons with a triple bond between C₃ & C₄ and four methyl groups, two on C₂ and another two on C₅.

Conclusion

The structure corresponding to the IUPAC name 2,2,5,5- tetramethyl-3-hexyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 6

Expert Solution

Interpretation Introduction

d) 3,4-Dimethylcyclodeceyne.

Interpretation:

The structure of 3,4-Dimethylcyclodeceyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 3,4-dimethyl cyclodeceyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3,4-dimethyl cyclodeceyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 7

Explanation of Solution

The name shows that the compound contains a ring made up of ten carbon atoms with a triple bond attached to two methyl groups on C₃ and C₄.

Conclusion

The structure corresponding to the IUPAC name 3,4-dimethyl cyclodeceyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 8

Expert Solution

Interpretation Introduction

e) 3,5-Heptadiene-1-yne.

Interpretation:

The structure of 3,5-heptadiene-1-yne is to be drawn.

Concept introduction:

The longest carbon chain which contains the carbon-carbon triple bond is chosen. The chain is numbered from the end that gives the lowest number to the carbon in triple bond. Compounds with more than one triple bond are called diynes, triynes and so forth. Compounds containing both double bond and triple bonds are called as enynes. The chain is numbered from the end nearer to the multiple bonds, double or triple. When there is a choice in numbering the double bond is given preference and the lowest number is assigned to it.

To draw:

The structure corresponding to the IUPAC name 3,5-heptadiene-1-yne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3,5-heptadiene-1-yne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 9

Explanation of Solution

The name shows that the longest carbon chain should contain seven carbons with a triple bond between C₁ & C₂ and two double bonds, one between C₃ & C₄ and another between C₅ & C₆.

Conclusion

The structure corresponding to the IUPAC name 3,5-heptadiene-1-yne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 10

Expert Solution

Interpretation Introduction

f) 3-Chloro-4,4-dimethyl-1-nonene-6-yne.

Interpretation:

The structure of 3-chloro-4,4-dimethyl-1-nonene-6-yne is to be drawn.

Concept introduction:

The longest carbon chain which contains the carbon-carbon triple bond is chosen. The chain is numbered from the end that gives the lowest number to the carbon in triple bond. Compounds with more than one triple bond are called diynes, triynes and so forth. Compounds containing both double bond and triple bonds are called as enynes. The chain is numbered from the end nearer to the multiple bonds, double or triple. When there is a choice in numbering the double bond is given preference and the lowest number is assigned to it.

To draw:

The structure corresponding to the IUPAC name 3-chloro-4,4-dimethyl-1-nonene-6-yne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3-chloro-4,4-dimethyl-1-nonene-6-yne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 11

Explanation of Solution

The name shows that the longest carbon chain should contain nine carbons with a triple bond between C₆ & C₇, one double bond between C₁ & C₂, a chlorine atom on C₃ and two methyl groups on C₄.

Conclusion

The structure corresponding to the IUPAC name 3-chloro-4,4-dimethyl-1-nonene-6-yne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 12

Expert Solution

Interpretation Introduction

g) 3-sec-Butyl-1-heptyne.

Interpretation:

The structure of 3-sec-Butyl-1-heptyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 3-sec-butyl-1-heptyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3-sec-butyl-1-heptyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 13

Explanation of Solution

The name shows that the longest carbon chain should contain seven carbons with a triple bond between C₁ & C₂ and a sec-butyl group on C₃.

Conclusion

The structure corresponding to the IUPAC name 3-sec-butyl-1-heptyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 14

Expert Solution

Interpretation Introduction

h) 5-tert-Butyl-2-methyl-3-octyne.

Interpretation:

The structure of 5-tert-Butyl-2-methyl-3-octyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 5-tert-Butyl-2-methyl-3-octyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 5-tert-Butyl-2-methyl-3-octyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 15

Explanation of Solution

The name shows that the longest carbon chain should contain eight carbons with a triple bond between C₃ & C₄, a tert-butyl group on C₅ and a methyl group on C₂.

Conclusion

The structure corresponding to the IUPAC name 5-tert-Butyl-2-methyl-3-octyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 16

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Answer 4

Textbook Question

Chapter 9.SE, Problem 27AP

Draw structures corresponding to the following names:

(a) 3, 3-Dimethyl-4-octyne

(b) 3-Ethyl-5-methyl-1, 6, 8-decatriyne

(c) 2, 2, 5, 5-Tetramethyl-3-hexyne

(d) 3, 4-Dimethylcyclodecyne

(e) 3, 5-Heptadien-1-yne

(f) 3-Chloro-4, 4-dimethyl-1-nonen-6-yne

(g) 3-sec-Butyl-1-heptyne

(h) 5-tert-Buty1-2-methyl-3-octyne

Expert Solution

Interpretation Introduction

a) 3,3-Dimethyl-4-octyne.

Interpretation:

The structure of 3,3-Dimethyl-4-octyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 3,3-dimethyl-4-octyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3,3-dimethyl-4-octyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 1

Explanation of Solution

The name shows that the longest carbon chain should contain eight carbons with a triple bond between C₄ & C₅ and two methyl groups should be present on C₃.

Conclusion

The structure corresponding to the IUPAC name 3,3-dimethyl-4-octyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 2

Expert Solution

Interpretation Introduction

b) 3-Ethyl-5-methyl-1,6,8-decatriyne.

Interpretation:

The structure of 3-ethyl-5-methyl-1,6,8-decatriyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 3-ethyl-5-methyl-1,6,8-decatriyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3-ethyl-5-methyl-1,6,8-decatriyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 3

Explanation of Solution

The name shows that the longest carbon chain should contain ten carbons with three triple bonds, one between C₁ & C₂, another between C₆ & C₇ a third one between C₈ & C₉, an ethyl group on C₃ and a methyl group on C₅.

Conclusion

The structure corresponding to the IUPAC name 3-ethyl-5-methyl-1,6,8-decatriyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 4

Expert Solution

Interpretation Introduction

c) 2,2,5,5- tetramethyl-3-hexyne.

Interpretation:

The structure of 2,2,5,5- tetramethyl-3-hexyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 2,2,5,5- tetramethyl-3-hexyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 2,2,5,5- tetramethyl-3-hexyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 5

Explanation of Solution

The name shows that the longest carbon chain should contain six carbons with a triple bond between C₃ & C₄ and four methyl groups, two on C₂ and another two on C₅.

Conclusion

The structure corresponding to the IUPAC name 2,2,5,5- tetramethyl-3-hexyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 6

Expert Solution

Interpretation Introduction

d) 3,4-Dimethylcyclodeceyne.

Interpretation:

The structure of 3,4-Dimethylcyclodeceyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 3,4-dimethyl cyclodeceyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3,4-dimethyl cyclodeceyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 7

Explanation of Solution

The name shows that the compound contains a ring made up of ten carbon atoms with a triple bond attached to two methyl groups on C₃ and C₄.

Conclusion

The structure corresponding to the IUPAC name 3,4-dimethyl cyclodeceyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 8

Expert Solution

Interpretation Introduction

e) 3,5-Heptadiene-1-yne.

Interpretation:

The structure of 3,5-heptadiene-1-yne is to be drawn.

Concept introduction:

The longest carbon chain which contains the carbon-carbon triple bond is chosen. The chain is numbered from the end that gives the lowest number to the carbon in triple bond. Compounds with more than one triple bond are called diynes, triynes and so forth. Compounds containing both double bond and triple bonds are called as enynes. The chain is numbered from the end nearer to the multiple bonds, double or triple. When there is a choice in numbering the double bond is given preference and the lowest number is assigned to it.

To draw:

The structure corresponding to the IUPAC name 3,5-heptadiene-1-yne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3,5-heptadiene-1-yne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 9

Explanation of Solution

The name shows that the longest carbon chain should contain seven carbons with a triple bond between C₁ & C₂ and two double bonds, one between C₃ & C₄ and another between C₅ & C₆.

Conclusion

The structure corresponding to the IUPAC name 3,5-heptadiene-1-yne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 10

Expert Solution

Interpretation Introduction

f) 3-Chloro-4,4-dimethyl-1-nonene-6-yne.

Interpretation:

The structure of 3-chloro-4,4-dimethyl-1-nonene-6-yne is to be drawn.

Concept introduction:

The longest carbon chain which contains the carbon-carbon triple bond is chosen. The chain is numbered from the end that gives the lowest number to the carbon in triple bond. Compounds with more than one triple bond are called diynes, triynes and so forth. Compounds containing both double bond and triple bonds are called as enynes. The chain is numbered from the end nearer to the multiple bonds, double or triple. When there is a choice in numbering the double bond is given preference and the lowest number is assigned to it.

To draw:

The structure corresponding to the IUPAC name 3-chloro-4,4-dimethyl-1-nonene-6-yne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3-chloro-4,4-dimethyl-1-nonene-6-yne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 11

Explanation of Solution

The name shows that the longest carbon chain should contain nine carbons with a triple bond between C₆ & C₇, one double bond between C₁ & C₂, a chlorine atom on C₃ and two methyl groups on C₄.

Conclusion

The structure corresponding to the IUPAC name 3-chloro-4,4-dimethyl-1-nonene-6-yne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 12

Expert Solution

Interpretation Introduction

g) 3-sec-Butyl-1-heptyne.

Interpretation:

The structure of 3-sec-Butyl-1-heptyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 3-sec-butyl-1-heptyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3-sec-butyl-1-heptyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 13

Explanation of Solution

The name shows that the longest carbon chain should contain seven carbons with a triple bond between C₁ & C₂ and a sec-butyl group on C₃.

Conclusion

The structure corresponding to the IUPAC name 3-sec-butyl-1-heptyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 14

Expert Solution

Interpretation Introduction

h) 5-tert-Butyl-2-methyl-3-octyne.

Interpretation:

The structure of 5-tert-Butyl-2-methyl-3-octyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 5-tert-Butyl-2-methyl-3-octyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 5-tert-Butyl-2-methyl-3-octyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 15

Explanation of Solution

The name shows that the longest carbon chain should contain eight carbons with a triple bond between C₃ & C₄, a tert-butyl group on C₅ and a methyl group on C₂.

Conclusion

The structure corresponding to the IUPAC name 5-tert-Butyl-2-methyl-3-octyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 16

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Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 5

Textbook Question

Answer 6

Textbook Question

Answer 7

Expert Solution

Interpretation Introduction

a) 3,3-Dimethyl-4-octyne.

Interpretation:

The structure of 3,3-Dimethyl-4-octyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 3,3-dimethyl-4-octyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3,3-dimethyl-4-octyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 1

Explanation of Solution

The name shows that the longest carbon chain should contain eight carbons with a triple bond between C₄ & C₅ and two methyl groups should be present on C₃.

Conclusion

The structure corresponding to the IUPAC name 3,3-dimethyl-4-octyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 2

Expert Solution

Interpretation Introduction

b) 3-Ethyl-5-methyl-1,6,8-decatriyne.

Interpretation:

The structure of 3-ethyl-5-methyl-1,6,8-decatriyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 3-ethyl-5-methyl-1,6,8-decatriyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3-ethyl-5-methyl-1,6,8-decatriyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 3

Explanation of Solution

The name shows that the longest carbon chain should contain ten carbons with three triple bonds, one between C₁ & C₂, another between C₆ & C₇ a third one between C₈ & C₉, an ethyl group on C₃ and a methyl group on C₅.

Conclusion

The structure corresponding to the IUPAC name 3-ethyl-5-methyl-1,6,8-decatriyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 4

Expert Solution

Interpretation Introduction

c) 2,2,5,5- tetramethyl-3-hexyne.

Interpretation:

The structure of 2,2,5,5- tetramethyl-3-hexyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 2,2,5,5- tetramethyl-3-hexyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 2,2,5,5- tetramethyl-3-hexyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 5

Explanation of Solution

The name shows that the longest carbon chain should contain six carbons with a triple bond between C₃ & C₄ and four methyl groups, two on C₂ and another two on C₅.

Conclusion

The structure corresponding to the IUPAC name 2,2,5,5- tetramethyl-3-hexyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 6

Expert Solution

Interpretation Introduction

d) 3,4-Dimethylcyclodeceyne.

Interpretation:

The structure of 3,4-Dimethylcyclodeceyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 3,4-dimethyl cyclodeceyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3,4-dimethyl cyclodeceyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 7

Explanation of Solution

The name shows that the compound contains a ring made up of ten carbon atoms with a triple bond attached to two methyl groups on C₃ and C₄.

Conclusion

The structure corresponding to the IUPAC name 3,4-dimethyl cyclodeceyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 8

Expert Solution

Interpretation Introduction

e) 3,5-Heptadiene-1-yne.

Interpretation:

The structure of 3,5-heptadiene-1-yne is to be drawn.

Concept introduction:

The longest carbon chain which contains the carbon-carbon triple bond is chosen. The chain is numbered from the end that gives the lowest number to the carbon in triple bond. Compounds with more than one triple bond are called diynes, triynes and so forth. Compounds containing both double bond and triple bonds are called as enynes. The chain is numbered from the end nearer to the multiple bonds, double or triple. When there is a choice in numbering the double bond is given preference and the lowest number is assigned to it.

To draw:

The structure corresponding to the IUPAC name 3,5-heptadiene-1-yne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3,5-heptadiene-1-yne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 9

Explanation of Solution

The name shows that the longest carbon chain should contain seven carbons with a triple bond between C₁ & C₂ and two double bonds, one between C₃ & C₄ and another between C₅ & C₆.

Conclusion

The structure corresponding to the IUPAC name 3,5-heptadiene-1-yne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 10

Expert Solution

Interpretation Introduction

f) 3-Chloro-4,4-dimethyl-1-nonene-6-yne.

Interpretation:

The structure of 3-chloro-4,4-dimethyl-1-nonene-6-yne is to be drawn.

Concept introduction:

The longest carbon chain which contains the carbon-carbon triple bond is chosen. The chain is numbered from the end that gives the lowest number to the carbon in triple bond. Compounds with more than one triple bond are called diynes, triynes and so forth. Compounds containing both double bond and triple bonds are called as enynes. The chain is numbered from the end nearer to the multiple bonds, double or triple. When there is a choice in numbering the double bond is given preference and the lowest number is assigned to it.

To draw:

The structure corresponding to the IUPAC name 3-chloro-4,4-dimethyl-1-nonene-6-yne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3-chloro-4,4-dimethyl-1-nonene-6-yne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 11

Explanation of Solution

The name shows that the longest carbon chain should contain nine carbons with a triple bond between C₆ & C₇, one double bond between C₁ & C₂, a chlorine atom on C₃ and two methyl groups on C₄.

Conclusion

The structure corresponding to the IUPAC name 3-chloro-4,4-dimethyl-1-nonene-6-yne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 12

Expert Solution

Interpretation Introduction

g) 3-sec-Butyl-1-heptyne.

Interpretation:

The structure of 3-sec-Butyl-1-heptyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 3-sec-butyl-1-heptyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3-sec-butyl-1-heptyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 13

Explanation of Solution

The name shows that the longest carbon chain should contain seven carbons with a triple bond between C₁ & C₂ and a sec-butyl group on C₃.

Conclusion

The structure corresponding to the IUPAC name 3-sec-butyl-1-heptyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 14

Expert Solution

Interpretation Introduction

h) 5-tert-Butyl-2-methyl-3-octyne.

Interpretation:

The structure of 5-tert-Butyl-2-methyl-3-octyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 5-tert-Butyl-2-methyl-3-octyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 5-tert-Butyl-2-methyl-3-octyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 15

Explanation of Solution

The name shows that the longest carbon chain should contain eight carbons with a triple bond between C₃ & C₄, a tert-butyl group on C₅ and a methyl group on C₂.

Conclusion

The structure corresponding to the IUPAC name 5-tert-Butyl-2-methyl-3-octyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 16

Answer 8

Expert Solution

Interpretation Introduction

a) 3,3-Dimethyl-4-octyne.

Interpretation:

The structure of 3,3-Dimethyl-4-octyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 3,3-dimethyl-4-octyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3,3-dimethyl-4-octyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 1

Explanation of Solution

The name shows that the longest carbon chain should contain eight carbons with a triple bond between C₄ & C₅ and two methyl groups should be present on C₃.

Conclusion

The structure corresponding to the IUPAC name 3,3-dimethyl-4-octyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 2

Answer 9

Expert Solution

Answer 10

Expert Solution

Answer 11

Expert Solution

Answer 12

Interpretation Introduction

a) 3,3-Dimethyl-4-octyne.

Interpretation:

The structure of 3,3-Dimethyl-4-octyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 3,3-dimethyl-4-octyne.

Answer 13

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3,3-dimethyl-4-octyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 1

Answer 14

Explanation of Solution

The name shows that the longest carbon chain should contain eight carbons with a triple bond between C₄ & C₅ and two methyl groups should be present on C₃.

Answer 15

Conclusion

The structure corresponding to the IUPAC name 3,3-dimethyl-4-octyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 2

Answer 16

Expert Solution

Interpretation Introduction

b) 3-Ethyl-5-methyl-1,6,8-decatriyne.

Interpretation:

The structure of 3-ethyl-5-methyl-1,6,8-decatriyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 3-ethyl-5-methyl-1,6,8-decatriyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3-ethyl-5-methyl-1,6,8-decatriyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 3

Explanation of Solution

The name shows that the longest carbon chain should contain ten carbons with three triple bonds, one between C₁ & C₂, another between C₆ & C₇ a third one between C₈ & C₉, an ethyl group on C₃ and a methyl group on C₅.

Conclusion

The structure corresponding to the IUPAC name 3-ethyl-5-methyl-1,6,8-decatriyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 4

Answer 17

Expert Solution

Answer 18

Expert Solution

Answer 19

Expert Solution

Answer 20

Interpretation Introduction

b) 3-Ethyl-5-methyl-1,6,8-decatriyne.

Interpretation:

The structure of 3-ethyl-5-methyl-1,6,8-decatriyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 3-ethyl-5-methyl-1,6,8-decatriyne.

Answer 21

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3-ethyl-5-methyl-1,6,8-decatriyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 3

Answer 22

Explanation of Solution

The name shows that the longest carbon chain should contain ten carbons with three triple bonds, one between C₁ & C₂, another between C₆ & C₇ a third one between C₈ & C₉, an ethyl group on C₃ and a methyl group on C₅.

Answer 23

Conclusion

The structure corresponding to the IUPAC name 3-ethyl-5-methyl-1,6,8-decatriyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 4

Answer 24

Expert Solution

Interpretation Introduction

c) 2,2,5,5- tetramethyl-3-hexyne.

Interpretation:

The structure of 2,2,5,5- tetramethyl-3-hexyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 2,2,5,5- tetramethyl-3-hexyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 2,2,5,5- tetramethyl-3-hexyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 5

Explanation of Solution

The name shows that the longest carbon chain should contain six carbons with a triple bond between C₃ & C₄ and four methyl groups, two on C₂ and another two on C₅.

Conclusion

The structure corresponding to the IUPAC name 2,2,5,5- tetramethyl-3-hexyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 6

Answer 25

Expert Solution

Answer 26

Expert Solution

Answer 27

Expert Solution

Answer 28

Interpretation Introduction

c) 2,2,5,5- tetramethyl-3-hexyne.

Interpretation:

The structure of 2,2,5,5- tetramethyl-3-hexyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 2,2,5,5- tetramethyl-3-hexyne.

Answer 29

Answer to Problem 27AP

The structure corresponding to the IUPAC name 2,2,5,5- tetramethyl-3-hexyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 5

Answer 30

Explanation of Solution

The name shows that the longest carbon chain should contain six carbons with a triple bond between C₃ & C₄ and four methyl groups, two on C₂ and another two on C₅.

Answer 31

Conclusion

The structure corresponding to the IUPAC name 2,2,5,5- tetramethyl-3-hexyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 6

Answer 32

Expert Solution

Interpretation Introduction

d) 3,4-Dimethylcyclodeceyne.

Interpretation:

The structure of 3,4-Dimethylcyclodeceyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 3,4-dimethyl cyclodeceyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3,4-dimethyl cyclodeceyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 7

Explanation of Solution

The name shows that the compound contains a ring made up of ten carbon atoms with a triple bond attached to two methyl groups on C₃ and C₄.

Conclusion

The structure corresponding to the IUPAC name 3,4-dimethyl cyclodeceyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 8

Answer 33

Expert Solution

Answer 34

Expert Solution

Answer 35

Expert Solution

Answer 36

Interpretation Introduction

d) 3,4-Dimethylcyclodeceyne.

Interpretation:

The structure of 3,4-Dimethylcyclodeceyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 3,4-dimethyl cyclodeceyne.

Answer 37

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3,4-dimethyl cyclodeceyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 7

Answer 38

Explanation of Solution

The name shows that the compound contains a ring made up of ten carbon atoms with a triple bond attached to two methyl groups on C₃ and C₄.

Answer 39

Conclusion

The structure corresponding to the IUPAC name 3,4-dimethyl cyclodeceyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 8

Answer 40

Expert Solution

Interpretation Introduction

e) 3,5-Heptadiene-1-yne.

Interpretation:

The structure of 3,5-heptadiene-1-yne is to be drawn.

Concept introduction:

The longest carbon chain which contains the carbon-carbon triple bond is chosen. The chain is numbered from the end that gives the lowest number to the carbon in triple bond. Compounds with more than one triple bond are called diynes, triynes and so forth. Compounds containing both double bond and triple bonds are called as enynes. The chain is numbered from the end nearer to the multiple bonds, double or triple. When there is a choice in numbering the double bond is given preference and the lowest number is assigned to it.

To draw:

The structure corresponding to the IUPAC name 3,5-heptadiene-1-yne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3,5-heptadiene-1-yne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 9

Explanation of Solution

The name shows that the longest carbon chain should contain seven carbons with a triple bond between C₁ & C₂ and two double bonds, one between C₃ & C₄ and another between C₅ & C₆.

Conclusion

The structure corresponding to the IUPAC name 3,5-heptadiene-1-yne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 10

Answer 41

Expert Solution

Answer 42

Expert Solution

Answer 43

Expert Solution

Answer 44

Interpretation Introduction

e) 3,5-Heptadiene-1-yne.

Interpretation:

The structure of 3,5-heptadiene-1-yne is to be drawn.

Concept introduction:

The longest carbon chain which contains the carbon-carbon triple bond is chosen. The chain is numbered from the end that gives the lowest number to the carbon in triple bond. Compounds with more than one triple bond are called diynes, triynes and so forth. Compounds containing both double bond and triple bonds are called as enynes. The chain is numbered from the end nearer to the multiple bonds, double or triple. When there is a choice in numbering the double bond is given preference and the lowest number is assigned to it.

To draw:

The structure corresponding to the IUPAC name 3,5-heptadiene-1-yne.

Answer 45

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3,5-heptadiene-1-yne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 9

Answer 46

Explanation of Solution

The name shows that the longest carbon chain should contain seven carbons with a triple bond between C₁ & C₂ and two double bonds, one between C₃ & C₄ and another between C₅ & C₆.

Answer 47

Conclusion

The structure corresponding to the IUPAC name 3,5-heptadiene-1-yne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 10

Answer 48

Expert Solution

Interpretation Introduction

f) 3-Chloro-4,4-dimethyl-1-nonene-6-yne.

Interpretation:

The structure of 3-chloro-4,4-dimethyl-1-nonene-6-yne is to be drawn.

Concept introduction:

The longest carbon chain which contains the carbon-carbon triple bond is chosen. The chain is numbered from the end that gives the lowest number to the carbon in triple bond. Compounds with more than one triple bond are called diynes, triynes and so forth. Compounds containing both double bond and triple bonds are called as enynes. The chain is numbered from the end nearer to the multiple bonds, double or triple. When there is a choice in numbering the double bond is given preference and the lowest number is assigned to it.

To draw:

The structure corresponding to the IUPAC name 3-chloro-4,4-dimethyl-1-nonene-6-yne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3-chloro-4,4-dimethyl-1-nonene-6-yne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 11

Explanation of Solution

The name shows that the longest carbon chain should contain nine carbons with a triple bond between C₆ & C₇, one double bond between C₁ & C₂, a chlorine atom on C₃ and two methyl groups on C₄.

Conclusion

The structure corresponding to the IUPAC name 3-chloro-4,4-dimethyl-1-nonene-6-yne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 12

Answer 49

Expert Solution

Answer 50

Expert Solution

Answer 51

Expert Solution

Answer 52

Interpretation Introduction

f) 3-Chloro-4,4-dimethyl-1-nonene-6-yne.

Interpretation:

The structure of 3-chloro-4,4-dimethyl-1-nonene-6-yne is to be drawn.

Concept introduction:

The longest carbon chain which contains the carbon-carbon triple bond is chosen. The chain is numbered from the end that gives the lowest number to the carbon in triple bond. Compounds with more than one triple bond are called diynes, triynes and so forth. Compounds containing both double bond and triple bonds are called as enynes. The chain is numbered from the end nearer to the multiple bonds, double or triple. When there is a choice in numbering the double bond is given preference and the lowest number is assigned to it.

To draw:

The structure corresponding to the IUPAC name 3-chloro-4,4-dimethyl-1-nonene-6-yne.

Answer 53

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3-chloro-4,4-dimethyl-1-nonene-6-yne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 11

Answer 54

Explanation of Solution

The name shows that the longest carbon chain should contain nine carbons with a triple bond between C₆ & C₇, one double bond between C₁ & C₂, a chlorine atom on C₃ and two methyl groups on C₄.

Answer 55

Conclusion

The structure corresponding to the IUPAC name 3-chloro-4,4-dimethyl-1-nonene-6-yne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 12

Answer 56

Expert Solution

Interpretation Introduction

g) 3-sec-Butyl-1-heptyne.

Interpretation:

The structure of 3-sec-Butyl-1-heptyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 3-sec-butyl-1-heptyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3-sec-butyl-1-heptyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 13

Explanation of Solution

The name shows that the longest carbon chain should contain seven carbons with a triple bond between C₁ & C₂ and a sec-butyl group on C₃.

Conclusion

The structure corresponding to the IUPAC name 3-sec-butyl-1-heptyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 14

Answer 57

Expert Solution

Answer 58

Expert Solution

Answer 59

Expert Solution

Answer 60

Interpretation Introduction

g) 3-sec-Butyl-1-heptyne.

Interpretation:

The structure of 3-sec-Butyl-1-heptyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 3-sec-butyl-1-heptyne.

Answer 61

Answer to Problem 27AP

The structure corresponding to the IUPAC name 3-sec-butyl-1-heptyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 13

Answer 62

Explanation of Solution

The name shows that the longest carbon chain should contain seven carbons with a triple bond between C₁ & C₂ and a sec-butyl group on C₃.

Answer 63

Conclusion

The structure corresponding to the IUPAC name 3-sec-butyl-1-heptyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 14

Answer 64

Expert Solution

Interpretation Introduction

h) 5-tert-Butyl-2-methyl-3-octyne.

Interpretation:

The structure of 5-tert-Butyl-2-methyl-3-octyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 5-tert-Butyl-2-methyl-3-octyne.

Answer to Problem 27AP

The structure corresponding to the IUPAC name 5-tert-Butyl-2-methyl-3-octyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 15

Explanation of Solution

The name shows that the longest carbon chain should contain eight carbons with a triple bond between C₃ & C₄, a tert-butyl group on C₅ and a methyl group on C₂.

Conclusion

The structure corresponding to the IUPAC name 5-tert-Butyl-2-methyl-3-octyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 16

Answer 65

Expert Solution

Answer 66

Expert Solution

Answer 67

Expert Solution

Answer 68

Interpretation Introduction

h) 5-tert-Butyl-2-methyl-3-octyne.

Interpretation:

The structure of 5-tert-Butyl-2-methyl-3-octyne is to be drawn.

Concept introduction:

The longest carbon chain containing the triple bond to be chosen. Based on the name of the parent compound–the alkyne name ends with the suffix–yne. The chain is to be numbered from the end that gives the lowest number to the carbon in triple bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the triple bond is indicated by giving the number of the first alkyne carbon before the name of the parent name. If more than one triple bond is present, their positions are indicated with the suffixes -diyne, -triyne and so on.

To draw:

The structure corresponding to the IUPAC name 5-tert-Butyl-2-methyl-3-octyne.

Answer 69

Answer to Problem 27AP

The structure corresponding to the IUPAC name 5-tert-Butyl-2-methyl-3-octyne is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 9.SE, Problem 27AP , additional homework tip 15

Answer 70

Explanation of Solution

The name shows that the longest carbon chain should contain eight carbons with a triple bond between C₃ & C₄, a tert-butyl group on C₅ and a methyl group on C₂.