Organic Chemistry
Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
Question
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Chapter 11, Problem 11.27P
Interpretation Introduction

(a)

Interpretation: The structure corresponding to the given name, 5,6dimethylhept2yne is to be identified.

Concept introduction: The systematic naming of organic compound is given by IUPAC. The full form of IUPAC is International Union of Pure and Applied Chemistry. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Expert Solution
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Answer to Problem 11.27P

The structure corresponding to the given name, 5,6dimethylhept2yne is,

Organic Chemistry, Chapter 11, Problem 11.27P , additional homework tip  1

Explanation of Solution

The structure corresponding to the given name, 5,6dimethylhept2yne is shown as,

Organic Chemistry, Chapter 11, Problem 11.27P , additional homework tip  2

Figure 1

This compound contains seven carbon atoms in the longest carbon chain and a triple bond at C2 position. Thus, the triple bond containing seven membered long chain of carbon is known to be 2heptyne. Two methyl groups are present at C5 and C6 positions. Hence, the IUPAC name of the given compound is 5,6dimethylhept2yne.

Conclusion

The structure corresponding to the given name is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation: The structure corresponding to the given name, 5tertbutyl6,6dimethylinon3yne is to be identified.

Concept introduction: The systematic naming of organic compound is given by IUPAC. The full form of IUPAC is International Union of Pure and Applied Chemistry. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Expert Solution
Check Mark

Answer to Problem 11.27P

The structure corresponding to the given name, 5tertbutyl6,6dimethylnon3yne is,

Organic Chemistry, Chapter 11, Problem 11.27P , additional homework tip  3

Explanation of Solution

The structure corresponding to the given name, 5tertbutyl6,6dimethylnon3yne is shown as,

Organic Chemistry, Chapter 11, Problem 11.27P , additional homework tip  4

Figure 2

This compound contains nine carbon atoms in the longest carbon chain and a triple bond at C3 position. Thus, the triple bond containing nine membered long chain of carbon is known to be non3yne. A tertiary butyl group is present at C5 position. Two methyl groups are present at C6 position. Hence, the IUPAC name of the given compound is 5tertbutyl6,6dimethylnon3yne.

Conclusion

The structure corresponding to the given name is shown in Figure 2.

Interpretation Introduction

(c)

Interpretation: The structure corresponding to the given name, (S)4chloropent2yne is to be identified.

Concept introduction: The systematic naming of organic compound is given by IUPAC. The full form of IUPAC is International Union of Pure and Applied Chemistry. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Expert Solution
Check Mark

Answer to Problem 11.27P

The structure corresponding to the given name, (S)4chloropent2yne is,

Organic Chemistry, Chapter 11, Problem 11.27P , additional homework tip  5

Explanation of Solution

The structure corresponding to the given name, (S)4chloropent2yne is shown as,

Organic Chemistry, Chapter 11, Problem 11.27P , additional homework tip  6

Figure 3

This compound contains five carbon atoms in the longest carbon chain and a triple bond at C2 position. Thus, the triple bond containing five membered long chain of carbon is known to be pent2yne. A chlorine substituent is present at C4 position. The S-configuration is assigned at C4 position after putting chlorine at wedge bond and hydrogen atom at hashed bond. Hence, the IUPAC name of the given compound is (S)4chloropent2yne.

Conclusion

The structure corresponding to the given name is shown in Figure 3.

Interpretation Introduction

(d)

Interpretation: The structure corresponding to the given name, cis1ethynyl2methylcyclopentane is to be identified.

Concept introduction: The systematic naming of organic compound is given by IUPAC. The full form of IUPAC is International Union of Pure and Applied Chemistry. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Expert Solution
Check Mark

Answer to Problem 11.27P

The structure corresponding to the given name, cis1ethynyl2methylcyclopentane is,

Organic Chemistry, Chapter 11, Problem 11.27P , additional homework tip  7

Explanation of Solution

The structure corresponding to the given name, cis1ethynyl2methylcyclopentane is shown as,

Organic Chemistry, Chapter 11, Problem 11.27P , additional homework tip  8

Figure 4

This compound contains five carbon atoms arranged in a cyclic carbon chain and a triple bond is present outside the cyclic chain. Thus, the five membered cyclic chain of carbon is known to be cyclopentane. One ethynyl group is present at C1 position and one methyl group is present at C2 position. The cis-configuration is assigned by placing both ethynyl and methyl group at wedge bonds. Hence, the IUPAC name of this compound is cis1ethynyl2methylcyclopentane.

Conclusion

The structure corresponding to the given name is shown in Figure 4.

Interpretation Introduction

(e)

Interpretation: The structure corresponding to the given name, 3,4dimethylocta1,5diyne is to be identified.

Concept introduction: The systematic naming of organic compound is given by IUPAC. The full form of IUPAC is International Union of Pure and Applied Chemistry. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Expert Solution
Check Mark

Answer to Problem 11.27P

The structure corresponding to the given name, 3,4dimethylocta1,5diyne is,

Organic Chemistry, Chapter 11, Problem 11.27P , additional homework tip  9

Explanation of Solution

The structure corresponding to the given name, 3,4dimethylocta1,5diyne is shown as,

Organic Chemistry, Chapter 11, Problem 11.27P , additional homework tip  10

Figure 5

This compound contains eight carbon atoms arranged in a longest carbon chain and two triple bonds are present at C1 and C5 positions. Thus, the triple bond containing eight membered long chain of carbon is known to be octa1,5diyne. Two methyl groups are present at C3 and C4 positions. Hence, the IUPAC name of this compound is 3,4dimethylocta1,5diyne.

Conclusion

The structure corresponding to the given name is shown in Figure 5.

Interpretation Introduction

(f)

Interpretation: The structure corresponding to the given name, (Z)6methylocta6ene1yne is to be identified.

Concept introduction: The systematic naming of organic compound is given by IUPAC. The full form of IUPAC is International Union of Pure and Applied Chemistry. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Expert Solution
Check Mark

Answer to Problem 11.27P

The structure corresponding to the given name, (Z)6methylocta6ene1yne is,

Organic Chemistry, Chapter 11, Problem 11.27P , additional homework tip  11

Explanation of Solution

The structure corresponding to the given name, (Z)6methylocta6ene1yne is shown as,

Organic Chemistry, Chapter 11, Problem 11.27P , additional homework tip  12

Figure 6

This compound contains eight carbon atoms arranged in a longest carbon chain, one double bond at C6 position and one triple bond are present at C1 position. Thus, the double and triple bonds containing eight membered long chain of carbon is known to be octa6ene1yne. One methyl group is present at C6 position. The (Z)-configuration is assigned at C6 position by placing two groups of high priority at the same side around the double bond. Hence, the IUPAC name of this compound is (Z)6methylocta6ene1yne.

Conclusion

The structure corresponding to the given name is shown in Figure 6.

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Chapter 11 Solutions

Organic Chemistry

Ch. 11 - Problem 11.11 Draw the keto tautomer of each...Ch. 11 - Prob. 11.12PCh. 11 - a Draw two different enol tautomers of...Ch. 11 - Prob. 11.14PCh. 11 - Problem 11.15 Draw the organic products formed in...Ch. 11 - Problem 11.16 What acetylide anion and alkyl...Ch. 11 - Problem. 11.17 Show how , and can be used to...Ch. 11 - Prob. 11.18PCh. 11 - Draw the products of each reaction. a. b.Ch. 11 - Prob. 11.20PCh. 11 - Problem 11.21 Use retrosynthetic analysis to show...Ch. 11 - Prob. 11.22PCh. 11 - Give the IUPAC name for each compound. a. b.Ch. 11 - Prob. 11.24PCh. 11 - 11.25 Answer the following questions about...Ch. 11 - 11.26 Give the IUPAC name for each alkyne. a. ...Ch. 11 - Prob. 11.27PCh. 11 - Which of the following pairs of compounds...Ch. 11 - Prob. 11.29PCh. 11 - 11.30 How is each compound related to A? Choose...Ch. 11 - Prob. 11.31PCh. 11 - Prob. 11.32PCh. 11 - 11.33 Draw the products formed when is treated...Ch. 11 - What reagents are needed to convert (CH3CH2)3CCCH...Ch. 11 - Prob. 11.35PCh. 11 - 11.36 What alkynes give each of the following...Ch. 11 - 11.37 What alkyne gives each compound as the only...Ch. 11 - 11.38 Draw the organic products formed in each...Ch. 11 - 11.39 Draw the structure of compounds A-E in the...Ch. 11 - Prob. 11.40PCh. 11 - Prob. 11.41PCh. 11 - 11.42 What reactions are needed to convert alcohol...Ch. 11 - Prob. 11.43PCh. 11 - Prob. 11.44PCh. 11 - 11.45 Explain the following statement. Although ...Ch. 11 - 11.46 Tautomerization in base resembles...Ch. 11 - 11.47 Draw a stepwise mechanism for each...Ch. 11 - Prob. 11.48PCh. 11 - Prob. 11.49PCh. 11 - 11.50 What acetylide anion and alkyl halide are...Ch. 11 - 11.51 Synthesize each compound from acetylene. You...Ch. 11 - 11.52 Devise a synthesis of each compound using ...Ch. 11 - Prob. 11.53PCh. 11 - Prob. 11.54PCh. 11 - 11.55 Devise a synthesis of the ketone, , from ...Ch. 11 - 11.56 Devise a synthesis of each compound using ...Ch. 11 - Prob. 11.57PCh. 11 - Prob. 11.58PCh. 11 - 11.59 N-Chlorosuccinimide (NCS) serves as a source...Ch. 11 - 11.60 Draw a stepwise mechanism for the following...Ch. 11 - 11.61 Draw a stepwise mechanism for the following...Ch. 11 - Prob. 11.62PCh. 11 - 11.63 Write a stepwise mechanism for each of the...Ch. 11 - Prob. 11.64PCh. 11 - 11.65 Explain why an optically active solution of ...
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