a) Bromoacetone Interpretation: The structure for bromoacetone is to be shown. Concept introduction: Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded carbon is considered as a substituent on the parent chain with the prefix –oxo. To show: The structure for bromoacetone.

Question

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Answer 1

Question

Chapter 19.SE, Problem 54AP

Interpretation Introduction

a) Bromoacetone

Interpretation:

The structure for bromoacetone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded carbon is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for bromoacetone.

Expert Solution

Answer to Problem 54AP

The structure of bromoacetone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 1

Explanation of Solution

The name indicates that the compound is a ketone with three carbon straight chain with a bromine atom attached to C₁.

Conclusion

The structure of bromoacetone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 2

Interpretation Introduction

b) (S)-2-Hydroxypropanal

Interpretation:

The structure for (S)-2-hydroxypropanal is to be shown.

Concept introduction:

Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.

To show:

The structure for (S)-2-hydroxypropanal.

Expert Solution

Answer to Problem 54AP

The structure of (S)-2-hydroxypropanal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 3

Explanation of Solution

The name indicates that the compound is an aldehyde with three carbon straight chain with a hydroxyl group attached to C₂. The molecule is chiral. The three groups, -OH(first highest priority), -CHO (second highest priority) and -CH₃(third highest priority) are arranged anticlockwise when viewed from the side away from H (fourth highest priority). Hence it has S stereochemistry.

Conclusion

The structure of (S)-2-hydroxypropanal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 4

Interpretation Introduction

c) 2-Methyl-3-heptanone

Interpretation:

The structure for 2-methyl-3-heptanone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for 2-methyl-3-heptanone.

Expert Solution

Answer to Problem 54AP

The structure of 2-methyl-3-heptanone is

Explanation of Solution

The name indicates that the compound is a ketone with seven carbon straight chain having the keto group at position three and a methyl group attached to C₂.

Conclusion

The structure of 2-methyl-3-heptanone is

Interpretation Introduction

d) (2S,3R)-2,3,4-Trihydroxybutanal

Interpretation:

The structure for (2S,3R)-2,3,4-trihydroxybutanal is to be shown.

Concept introduction:

Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.

To show:

The structure for (2S,3R)-2,3,4-trihydroxybutanal.

Expert Solution

Answer to Problem 54AP

The structure of (2S,3R)-2,3,4-trihydroxybutanal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 5

Explanation of Solution

The name indicates that the compound is an aldehyde with four carbon straight chain and has three hydroxyl groups attached to C₂, C₃ and C₄.

The molecule is chiral. The C₂ is attached to the three groups, -OH(first highest priority), -CHO (second highest priority) and –C₃ (third highest priority) arranged anticlockwise when viewed from the side away from H (fourth highest priority). Hence it has S stereochemistry.

The C₃ is attached to the three groups, -OH(first highest priority), –C₂ (second highest priority) and –CH₂OH--(third highest priority) arranged clockwise when viewed from the side away from H (fourth highest priority). Hence it has R stereochemistry.

Conclusion

The structure of (2S,3R)-2,3,4-trihydroxybutanal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 6

Interpretation Introduction

e) 2,2,4,4-Tetramethyl-3-pentanone

Interpretation:

The structure for 2,2,4,4-tetramethyl-3-pentanone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for 2,2,4,4-tetramethyl-3-pentanone.

Expert Solution

Answer to Problem 54AP

The structure of 2,2,4,4-tetramethyl-3-pentanone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 7

Explanation of Solution

The name indicates that the compound is a ketone with five carbon straight chain with a keto group at position three attached to four methyl groups, two on C₂ and other two on C₄.

Conclusion

The structure of 2,2,4,4-Tetramethyl-3-pentanone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 8

Interpretation Introduction

f) 4-methyl-3-penten-2-one

Interpretation:

The structure for 4-methyl-3-penten-2-one is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for 4-methyl-3-penten-2-one.

Expert Solution

Answer to Problem 54AP

The structure of 4-methyl-3-penten-2-one is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 9

Explanation of Solution

The name indicates that the compound is a ketone containing a five carbon straight chain, having a keto group at position two and a double bond between C₃ and C₄ with a methyl group on C₄.

Conclusion

The structure of 4-methyl-3-penten-2-one is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 10

Interpretation Introduction

g) Butanedial

Interpretation:

The structure for butanedial is to be shown.

Concept introduction:

Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.

To show:

The structure for butanedial.

Expert Solution

Answer to Problem 54AP

The structure of butanedial is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 11

Explanation of Solution

The name of the compound indicates that it has a four carbon straight chain with two aldehyde groups at both ends.

Conclusion

The structure of butanedial is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 12

Interpretation Introduction

h) 3-Phenyl-2-propenal

Interpretation:

The structure for 3-phenyl-2-propenal is to be shown.

Concept introduction:

Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.

To show:

The structure for 3-phenyl-2-propenal.

Expert Solution

Answer to Problem 54AP

The structure of 3-phenyl-2-propenal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 13

Explanation of Solution

The name of the compound indicates that the compound is a three carbon aldehyde with a double bond between C₂ & C₃ and has a phenyl group attached to C₃.

Conclusion

The structure of 3-phenyl-2-propenal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 14

Interpretation Introduction

i) 6,6-Dimethyl-2,4-cyclohexadienone

Interpretation:

The structure for 6,6-dimethyl-2,4-cyclohexadienone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for 6,6-dimethyl-2,4-cyclohexadienone.

Expert Solution

Answer to Problem 54AP

The structure of 6,6-dimethyl-2,4-cyclohexadienone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 15

Explanation of Solution

The name of the compound indicates that it is a cyclic ketone with a cyclohexadiene ring containing two double bonds, one between C₂ & C₃ and other between C₄ & C₅. It also has two methyl groups on C₆.

Conclusion

The structure of 6,6-dimethyl-2,4-cyclohexadienone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 16

Interpretation Introduction

j) p-Nitroacetophenone

Interpretation:

The structure for p-nitroacetophenone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo. Some common names like acetophenone are retained by IUPAC.

To show:

The structure for p-nitroacetophenone.

Expert Solution

Answer to Problem 54AP

The structure of p-nitroacetophenone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 17

Explanation of Solution

The name of the compound indicates that it contains an actyl and nitro groups attached to a benzene ring in para relationship.

Conclusion

The structure of p-nitroacetophenone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 18

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Answer 2

Question

Chapter 19.SE, Problem 54AP

Interpretation Introduction

a) Bromoacetone

Interpretation:

The structure for bromoacetone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded carbon is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for bromoacetone.

Expert Solution

Answer to Problem 54AP

The structure of bromoacetone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 1

Explanation of Solution

The name indicates that the compound is a ketone with three carbon straight chain with a bromine atom attached to C₁.

Conclusion

The structure of bromoacetone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 2

Interpretation Introduction

b) (S)-2-Hydroxypropanal

Interpretation:

The structure for (S)-2-hydroxypropanal is to be shown.

Concept introduction:

Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.

To show:

The structure for (S)-2-hydroxypropanal.

Expert Solution

Answer to Problem 54AP

The structure of (S)-2-hydroxypropanal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 3

Explanation of Solution

The name indicates that the compound is an aldehyde with three carbon straight chain with a hydroxyl group attached to C₂. The molecule is chiral. The three groups, -OH(first highest priority), -CHO (second highest priority) and -CH₃(third highest priority) are arranged anticlockwise when viewed from the side away from H (fourth highest priority). Hence it has S stereochemistry.

Conclusion

The structure of (S)-2-hydroxypropanal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 4

Interpretation Introduction

c) 2-Methyl-3-heptanone

Interpretation:

The structure for 2-methyl-3-heptanone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for 2-methyl-3-heptanone.

Expert Solution

Answer to Problem 54AP

The structure of 2-methyl-3-heptanone is

Explanation of Solution

The name indicates that the compound is a ketone with seven carbon straight chain having the keto group at position three and a methyl group attached to C₂.

Conclusion

The structure of 2-methyl-3-heptanone is

Interpretation Introduction

d) (2S,3R)-2,3,4-Trihydroxybutanal

Interpretation:

The structure for (2S,3R)-2,3,4-trihydroxybutanal is to be shown.

Concept introduction:

Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.

To show:

The structure for (2S,3R)-2,3,4-trihydroxybutanal.

Expert Solution

Answer to Problem 54AP

The structure of (2S,3R)-2,3,4-trihydroxybutanal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 5

Explanation of Solution

The name indicates that the compound is an aldehyde with four carbon straight chain and has three hydroxyl groups attached to C₂, C₃ and C₄.

The molecule is chiral. The C₂ is attached to the three groups, -OH(first highest priority), -CHO (second highest priority) and –C₃ (third highest priority) arranged anticlockwise when viewed from the side away from H (fourth highest priority). Hence it has S stereochemistry.

The C₃ is attached to the three groups, -OH(first highest priority), –C₂ (second highest priority) and –CH₂OH--(third highest priority) arranged clockwise when viewed from the side away from H (fourth highest priority). Hence it has R stereochemistry.

Conclusion

The structure of (2S,3R)-2,3,4-trihydroxybutanal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 6

Interpretation Introduction

e) 2,2,4,4-Tetramethyl-3-pentanone

Interpretation:

The structure for 2,2,4,4-tetramethyl-3-pentanone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for 2,2,4,4-tetramethyl-3-pentanone.

Expert Solution

Answer to Problem 54AP

The structure of 2,2,4,4-tetramethyl-3-pentanone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 7

Explanation of Solution

The name indicates that the compound is a ketone with five carbon straight chain with a keto group at position three attached to four methyl groups, two on C₂ and other two on C₄.

Conclusion

The structure of 2,2,4,4-Tetramethyl-3-pentanone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 8

Interpretation Introduction

f) 4-methyl-3-penten-2-one

Interpretation:

The structure for 4-methyl-3-penten-2-one is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for 4-methyl-3-penten-2-one.

Expert Solution

Answer to Problem 54AP

The structure of 4-methyl-3-penten-2-one is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 9

Explanation of Solution

The name indicates that the compound is a ketone containing a five carbon straight chain, having a keto group at position two and a double bond between C₃ and C₄ with a methyl group on C₄.

Conclusion

The structure of 4-methyl-3-penten-2-one is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 10

Interpretation Introduction

g) Butanedial

Interpretation:

The structure for butanedial is to be shown.

Concept introduction:

Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.

To show:

The structure for butanedial.

Expert Solution

Answer to Problem 54AP

The structure of butanedial is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 11

Explanation of Solution

The name of the compound indicates that it has a four carbon straight chain with two aldehyde groups at both ends.

Conclusion

The structure of butanedial is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 12

Interpretation Introduction

h) 3-Phenyl-2-propenal

Interpretation:

The structure for 3-phenyl-2-propenal is to be shown.

Concept introduction:

Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.

To show:

The structure for 3-phenyl-2-propenal.

Expert Solution

Answer to Problem 54AP

The structure of 3-phenyl-2-propenal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 13

Explanation of Solution

The name of the compound indicates that the compound is a three carbon aldehyde with a double bond between C₂ & C₃ and has a phenyl group attached to C₃.

Conclusion

The structure of 3-phenyl-2-propenal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 14

Interpretation Introduction

i) 6,6-Dimethyl-2,4-cyclohexadienone

Interpretation:

The structure for 6,6-dimethyl-2,4-cyclohexadienone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for 6,6-dimethyl-2,4-cyclohexadienone.

Expert Solution

Answer to Problem 54AP

The structure of 6,6-dimethyl-2,4-cyclohexadienone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 15

Explanation of Solution

The name of the compound indicates that it is a cyclic ketone with a cyclohexadiene ring containing two double bonds, one between C₂ & C₃ and other between C₄ & C₅. It also has two methyl groups on C₆.

Conclusion

The structure of 6,6-dimethyl-2,4-cyclohexadienone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 16

Interpretation Introduction

j) p-Nitroacetophenone

Interpretation:

The structure for p-nitroacetophenone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo. Some common names like acetophenone are retained by IUPAC.

To show:

The structure for p-nitroacetophenone.

Expert Solution

Answer to Problem 54AP

The structure of p-nitroacetophenone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 17

Explanation of Solution

The name of the compound indicates that it contains an actyl and nitro groups attached to a benzene ring in para relationship.

Conclusion

The structure of p-nitroacetophenone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 18

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

Answer 3

Question

Chapter 19.SE, Problem 54AP

Interpretation Introduction

a) Bromoacetone

Interpretation:

The structure for bromoacetone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded carbon is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for bromoacetone.

Expert Solution

Answer to Problem 54AP

The structure of bromoacetone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 1

Explanation of Solution

The name indicates that the compound is a ketone with three carbon straight chain with a bromine atom attached to C₁.

Conclusion

The structure of bromoacetone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 2

Interpretation Introduction

b) (S)-2-Hydroxypropanal

Interpretation:

The structure for (S)-2-hydroxypropanal is to be shown.

Concept introduction:

Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.

To show:

The structure for (S)-2-hydroxypropanal.

Expert Solution

Answer to Problem 54AP

The structure of (S)-2-hydroxypropanal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 3

Explanation of Solution

The name indicates that the compound is an aldehyde with three carbon straight chain with a hydroxyl group attached to C₂. The molecule is chiral. The three groups, -OH(first highest priority), -CHO (second highest priority) and -CH₃(third highest priority) are arranged anticlockwise when viewed from the side away from H (fourth highest priority). Hence it has S stereochemistry.

Conclusion

The structure of (S)-2-hydroxypropanal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 4

Interpretation Introduction

c) 2-Methyl-3-heptanone

Interpretation:

The structure for 2-methyl-3-heptanone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for 2-methyl-3-heptanone.

Expert Solution

Answer to Problem 54AP

The structure of 2-methyl-3-heptanone is

Explanation of Solution

The name indicates that the compound is a ketone with seven carbon straight chain having the keto group at position three and a methyl group attached to C₂.

Conclusion

The structure of 2-methyl-3-heptanone is

Interpretation Introduction

d) (2S,3R)-2,3,4-Trihydroxybutanal

Interpretation:

The structure for (2S,3R)-2,3,4-trihydroxybutanal is to be shown.

Concept introduction:

Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.

To show:

The structure for (2S,3R)-2,3,4-trihydroxybutanal.

Expert Solution

Answer to Problem 54AP

The structure of (2S,3R)-2,3,4-trihydroxybutanal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 5

Explanation of Solution

The name indicates that the compound is an aldehyde with four carbon straight chain and has three hydroxyl groups attached to C₂, C₃ and C₄.

The molecule is chiral. The C₂ is attached to the three groups, -OH(first highest priority), -CHO (second highest priority) and –C₃ (third highest priority) arranged anticlockwise when viewed from the side away from H (fourth highest priority). Hence it has S stereochemistry.

The C₃ is attached to the three groups, -OH(first highest priority), –C₂ (second highest priority) and –CH₂OH--(third highest priority) arranged clockwise when viewed from the side away from H (fourth highest priority). Hence it has R stereochemistry.

Conclusion

The structure of (2S,3R)-2,3,4-trihydroxybutanal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 6

Interpretation Introduction

e) 2,2,4,4-Tetramethyl-3-pentanone

Interpretation:

The structure for 2,2,4,4-tetramethyl-3-pentanone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for 2,2,4,4-tetramethyl-3-pentanone.

Expert Solution

Answer to Problem 54AP

The structure of 2,2,4,4-tetramethyl-3-pentanone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 7

Explanation of Solution

The name indicates that the compound is a ketone with five carbon straight chain with a keto group at position three attached to four methyl groups, two on C₂ and other two on C₄.

Conclusion

The structure of 2,2,4,4-Tetramethyl-3-pentanone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 8

Interpretation Introduction

f) 4-methyl-3-penten-2-one

Interpretation:

The structure for 4-methyl-3-penten-2-one is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for 4-methyl-3-penten-2-one.

Expert Solution

Answer to Problem 54AP

The structure of 4-methyl-3-penten-2-one is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 9

Explanation of Solution

The name indicates that the compound is a ketone containing a five carbon straight chain, having a keto group at position two and a double bond between C₃ and C₄ with a methyl group on C₄.

Conclusion

The structure of 4-methyl-3-penten-2-one is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 10

Interpretation Introduction

g) Butanedial

Interpretation:

The structure for butanedial is to be shown.

Concept introduction:

Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.

To show:

The structure for butanedial.

Expert Solution

Answer to Problem 54AP

The structure of butanedial is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 11

Explanation of Solution

The name of the compound indicates that it has a four carbon straight chain with two aldehyde groups at both ends.

Conclusion

The structure of butanedial is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 12

Interpretation Introduction

h) 3-Phenyl-2-propenal

Interpretation:

The structure for 3-phenyl-2-propenal is to be shown.

Concept introduction:

Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.

To show:

The structure for 3-phenyl-2-propenal.

Expert Solution

Answer to Problem 54AP

The structure of 3-phenyl-2-propenal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 13

Explanation of Solution

The name of the compound indicates that the compound is a three carbon aldehyde with a double bond between C₂ & C₃ and has a phenyl group attached to C₃.

Conclusion

The structure of 3-phenyl-2-propenal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 14

Interpretation Introduction

i) 6,6-Dimethyl-2,4-cyclohexadienone

Interpretation:

The structure for 6,6-dimethyl-2,4-cyclohexadienone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for 6,6-dimethyl-2,4-cyclohexadienone.

Expert Solution

Answer to Problem 54AP

The structure of 6,6-dimethyl-2,4-cyclohexadienone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 15

Explanation of Solution

The name of the compound indicates that it is a cyclic ketone with a cyclohexadiene ring containing two double bonds, one between C₂ & C₃ and other between C₄ & C₅. It also has two methyl groups on C₆.

Conclusion

The structure of 6,6-dimethyl-2,4-cyclohexadienone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 16

Interpretation Introduction

j) p-Nitroacetophenone

Interpretation:

The structure for p-nitroacetophenone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo. Some common names like acetophenone are retained by IUPAC.

To show:

The structure for p-nitroacetophenone.

Expert Solution

Answer to Problem 54AP

The structure of p-nitroacetophenone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 17

Explanation of Solution

The name of the compound indicates that it contains an actyl and nitro groups attached to a benzene ring in para relationship.

Conclusion

The structure of p-nitroacetophenone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 18

Want to see more full solutions like this?

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

Answer 4

Question

Chapter 19.SE, Problem 54AP

Interpretation Introduction

a) Bromoacetone

Interpretation:

The structure for bromoacetone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded carbon is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for bromoacetone.

Expert Solution

Answer to Problem 54AP

The structure of bromoacetone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 1

Explanation of Solution

The name indicates that the compound is a ketone with three carbon straight chain with a bromine atom attached to C₁.

Conclusion

The structure of bromoacetone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 2

Interpretation Introduction

b) (S)-2-Hydroxypropanal

Interpretation:

The structure for (S)-2-hydroxypropanal is to be shown.

Concept introduction:

Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.

To show:

The structure for (S)-2-hydroxypropanal.

Expert Solution

Answer to Problem 54AP

The structure of (S)-2-hydroxypropanal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 3

Explanation of Solution

The name indicates that the compound is an aldehyde with three carbon straight chain with a hydroxyl group attached to C₂. The molecule is chiral. The three groups, -OH(first highest priority), -CHO (second highest priority) and -CH₃(third highest priority) are arranged anticlockwise when viewed from the side away from H (fourth highest priority). Hence it has S stereochemistry.

Conclusion

The structure of (S)-2-hydroxypropanal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 4

Interpretation Introduction

c) 2-Methyl-3-heptanone

Interpretation:

The structure for 2-methyl-3-heptanone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for 2-methyl-3-heptanone.

Expert Solution

Answer to Problem 54AP

The structure of 2-methyl-3-heptanone is

Explanation of Solution

The name indicates that the compound is a ketone with seven carbon straight chain having the keto group at position three and a methyl group attached to C₂.

Conclusion

The structure of 2-methyl-3-heptanone is

Interpretation Introduction

d) (2S,3R)-2,3,4-Trihydroxybutanal

Interpretation:

The structure for (2S,3R)-2,3,4-trihydroxybutanal is to be shown.

Concept introduction:

Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.

To show:

The structure for (2S,3R)-2,3,4-trihydroxybutanal.

Expert Solution

Answer to Problem 54AP

The structure of (2S,3R)-2,3,4-trihydroxybutanal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 5

Explanation of Solution

The name indicates that the compound is an aldehyde with four carbon straight chain and has three hydroxyl groups attached to C₂, C₃ and C₄.

The molecule is chiral. The C₂ is attached to the three groups, -OH(first highest priority), -CHO (second highest priority) and –C₃ (third highest priority) arranged anticlockwise when viewed from the side away from H (fourth highest priority). Hence it has S stereochemistry.

The C₃ is attached to the three groups, -OH(first highest priority), –C₂ (second highest priority) and –CH₂OH--(third highest priority) arranged clockwise when viewed from the side away from H (fourth highest priority). Hence it has R stereochemistry.

Conclusion

The structure of (2S,3R)-2,3,4-trihydroxybutanal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 6

Interpretation Introduction

e) 2,2,4,4-Tetramethyl-3-pentanone

Interpretation:

The structure for 2,2,4,4-tetramethyl-3-pentanone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for 2,2,4,4-tetramethyl-3-pentanone.

Expert Solution

Answer to Problem 54AP

The structure of 2,2,4,4-tetramethyl-3-pentanone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 7

Explanation of Solution

The name indicates that the compound is a ketone with five carbon straight chain with a keto group at position three attached to four methyl groups, two on C₂ and other two on C₄.

Conclusion

The structure of 2,2,4,4-Tetramethyl-3-pentanone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 8

Interpretation Introduction

f) 4-methyl-3-penten-2-one

Interpretation:

The structure for 4-methyl-3-penten-2-one is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for 4-methyl-3-penten-2-one.

Expert Solution

Answer to Problem 54AP

The structure of 4-methyl-3-penten-2-one is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 9

Explanation of Solution

The name indicates that the compound is a ketone containing a five carbon straight chain, having a keto group at position two and a double bond between C₃ and C₄ with a methyl group on C₄.

Conclusion

The structure of 4-methyl-3-penten-2-one is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 10

Interpretation Introduction

g) Butanedial

Interpretation:

The structure for butanedial is to be shown.

Concept introduction:

Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.

To show:

The structure for butanedial.

Expert Solution

Answer to Problem 54AP

The structure of butanedial is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 11

Explanation of Solution

The name of the compound indicates that it has a four carbon straight chain with two aldehyde groups at both ends.

Conclusion

The structure of butanedial is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 12

Interpretation Introduction

h) 3-Phenyl-2-propenal

Interpretation:

The structure for 3-phenyl-2-propenal is to be shown.

Concept introduction:

Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.

To show:

The structure for 3-phenyl-2-propenal.

Expert Solution

Answer to Problem 54AP

The structure of 3-phenyl-2-propenal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 13

Explanation of Solution

The name of the compound indicates that the compound is a three carbon aldehyde with a double bond between C₂ & C₃ and has a phenyl group attached to C₃.

Conclusion

The structure of 3-phenyl-2-propenal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 14

Interpretation Introduction

i) 6,6-Dimethyl-2,4-cyclohexadienone

Interpretation:

The structure for 6,6-dimethyl-2,4-cyclohexadienone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for 6,6-dimethyl-2,4-cyclohexadienone.

Expert Solution

Answer to Problem 54AP

The structure of 6,6-dimethyl-2,4-cyclohexadienone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 15

Explanation of Solution

The name of the compound indicates that it is a cyclic ketone with a cyclohexadiene ring containing two double bonds, one between C₂ & C₃ and other between C₄ & C₅. It also has two methyl groups on C₆.

Conclusion

The structure of 6,6-dimethyl-2,4-cyclohexadienone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 16

Interpretation Introduction

j) p-Nitroacetophenone

Interpretation:

The structure for p-nitroacetophenone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo. Some common names like acetophenone are retained by IUPAC.

To show:

The structure for p-nitroacetophenone.

Expert Solution

Answer to Problem 54AP

The structure of p-nitroacetophenone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 17

Explanation of Solution

The name of the compound indicates that it contains an actyl and nitro groups attached to a benzene ring in para relationship.

Conclusion

The structure of p-nitroacetophenone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 18

Want to see more full solutions like this?

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

Answer 5

Chapter 19.SE, Problem 54AP

Interpretation Introduction

a) Bromoacetone

Interpretation:

The structure for bromoacetone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded carbon is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for bromoacetone.

Expert Solution

Answer to Problem 54AP

The structure of bromoacetone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 1

Explanation of Solution

The name indicates that the compound is a ketone with three carbon straight chain with a bromine atom attached to C₁.

Conclusion

The structure of bromoacetone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 2

Interpretation Introduction

b) (S)-2-Hydroxypropanal

Interpretation:

The structure for (S)-2-hydroxypropanal is to be shown.

Concept introduction:

Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.

To show:

The structure for (S)-2-hydroxypropanal.

Expert Solution

Answer to Problem 54AP

The structure of (S)-2-hydroxypropanal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 3

Explanation of Solution

The name indicates that the compound is an aldehyde with three carbon straight chain with a hydroxyl group attached to C₂. The molecule is chiral. The three groups, -OH(first highest priority), -CHO (second highest priority) and -CH₃(third highest priority) are arranged anticlockwise when viewed from the side away from H (fourth highest priority). Hence it has S stereochemistry.

Conclusion

The structure of (S)-2-hydroxypropanal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 4

Interpretation Introduction

c) 2-Methyl-3-heptanone

Interpretation:

The structure for 2-methyl-3-heptanone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for 2-methyl-3-heptanone.

Expert Solution

Answer to Problem 54AP

The structure of 2-methyl-3-heptanone is

Explanation of Solution

The name indicates that the compound is a ketone with seven carbon straight chain having the keto group at position three and a methyl group attached to C₂.

Conclusion

The structure of 2-methyl-3-heptanone is

Interpretation Introduction

d) (2S,3R)-2,3,4-Trihydroxybutanal

Interpretation:

The structure for (2S,3R)-2,3,4-trihydroxybutanal is to be shown.

Concept introduction:

Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.

To show:

The structure for (2S,3R)-2,3,4-trihydroxybutanal.

Expert Solution

Answer to Problem 54AP

The structure of (2S,3R)-2,3,4-trihydroxybutanal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 5

Explanation of Solution

The name indicates that the compound is an aldehyde with four carbon straight chain and has three hydroxyl groups attached to C₂, C₃ and C₄.

The molecule is chiral. The C₂ is attached to the three groups, -OH(first highest priority), -CHO (second highest priority) and –C₃ (third highest priority) arranged anticlockwise when viewed from the side away from H (fourth highest priority). Hence it has S stereochemistry.

The C₃ is attached to the three groups, -OH(first highest priority), –C₂ (second highest priority) and –CH₂OH--(third highest priority) arranged clockwise when viewed from the side away from H (fourth highest priority). Hence it has R stereochemistry.

Conclusion

The structure of (2S,3R)-2,3,4-trihydroxybutanal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 6

Interpretation Introduction

e) 2,2,4,4-Tetramethyl-3-pentanone

Interpretation:

The structure for 2,2,4,4-tetramethyl-3-pentanone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for 2,2,4,4-tetramethyl-3-pentanone.

Expert Solution

Answer to Problem 54AP

The structure of 2,2,4,4-tetramethyl-3-pentanone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 7

Explanation of Solution

The name indicates that the compound is a ketone with five carbon straight chain with a keto group at position three attached to four methyl groups, two on C₂ and other two on C₄.

Conclusion

The structure of 2,2,4,4-Tetramethyl-3-pentanone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 8

Interpretation Introduction

f) 4-methyl-3-penten-2-one

Interpretation:

The structure for 4-methyl-3-penten-2-one is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for 4-methyl-3-penten-2-one.

Expert Solution

Answer to Problem 54AP

The structure of 4-methyl-3-penten-2-one is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 9

Explanation of Solution

The name indicates that the compound is a ketone containing a five carbon straight chain, having a keto group at position two and a double bond between C₃ and C₄ with a methyl group on C₄.

Conclusion

The structure of 4-methyl-3-penten-2-one is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 10

Interpretation Introduction

g) Butanedial

Interpretation:

The structure for butanedial is to be shown.

Concept introduction:

Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.

To show:

The structure for butanedial.

Expert Solution

Answer to Problem 54AP

The structure of butanedial is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 11

Explanation of Solution

The name of the compound indicates that it has a four carbon straight chain with two aldehyde groups at both ends.

Conclusion

The structure of butanedial is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 12

Interpretation Introduction

h) 3-Phenyl-2-propenal

Interpretation:

The structure for 3-phenyl-2-propenal is to be shown.

Concept introduction:

Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.

To show:

The structure for 3-phenyl-2-propenal.

Expert Solution

Answer to Problem 54AP

The structure of 3-phenyl-2-propenal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 13

Explanation of Solution

The name of the compound indicates that the compound is a three carbon aldehyde with a double bond between C₂ & C₃ and has a phenyl group attached to C₃.

Conclusion

The structure of 3-phenyl-2-propenal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 14

Interpretation Introduction

i) 6,6-Dimethyl-2,4-cyclohexadienone

Interpretation:

The structure for 6,6-dimethyl-2,4-cyclohexadienone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for 6,6-dimethyl-2,4-cyclohexadienone.

Expert Solution

Answer to Problem 54AP

The structure of 6,6-dimethyl-2,4-cyclohexadienone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 15

Explanation of Solution

The name of the compound indicates that it is a cyclic ketone with a cyclohexadiene ring containing two double bonds, one between C₂ & C₃ and other between C₄ & C₅. It also has two methyl groups on C₆.

Conclusion

The structure of 6,6-dimethyl-2,4-cyclohexadienone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 16

Interpretation Introduction

j) p-Nitroacetophenone

Interpretation:

The structure for p-nitroacetophenone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo. Some common names like acetophenone are retained by IUPAC.

To show:

The structure for p-nitroacetophenone.

Expert Solution

Answer to Problem 54AP

The structure of p-nitroacetophenone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 17

Explanation of Solution

The name of the compound indicates that it contains an actyl and nitro groups attached to a benzene ring in para relationship.

Conclusion

The structure of p-nitroacetophenone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 18

Answer 6

Chapter 19.SE, Problem 54AP

Interpretation Introduction

a) Bromoacetone

Interpretation:

The structure for bromoacetone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded carbon is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for bromoacetone.

Expert Solution

Answer to Problem 54AP

The structure of bromoacetone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 1

Explanation of Solution

The name indicates that the compound is a ketone with three carbon straight chain with a bromine atom attached to C₁.

Conclusion

The structure of bromoacetone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 2

Answer 7

Chapter 19.SE, Problem 54AP

Interpretation Introduction

a) Bromoacetone

Interpretation:

The structure for bromoacetone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded carbon is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for bromoacetone.

Answer 8

Expert Solution

Answer to Problem 54AP

The structure of bromoacetone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 1

Answer 9

Expert Solution

Answer 10

Expert Solution

Answer 11

Expert Solution

Answer 12

Explanation of Solution

The name indicates that the compound is a ketone with three carbon straight chain with a bromine atom attached to C₁.

Answer 13

Conclusion

The structure of bromoacetone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 2

Answer 14

Interpretation Introduction

b) (S)-2-Hydroxypropanal

Interpretation:

The structure for (S)-2-hydroxypropanal is to be shown.

Concept introduction:

Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.

To show:

The structure for (S)-2-hydroxypropanal.

Expert Solution

Answer to Problem 54AP

The structure of (S)-2-hydroxypropanal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 3

Explanation of Solution

The name indicates that the compound is an aldehyde with three carbon straight chain with a hydroxyl group attached to C₂. The molecule is chiral. The three groups, -OH(first highest priority), -CHO (second highest priority) and -CH₃(third highest priority) are arranged anticlockwise when viewed from the side away from H (fourth highest priority). Hence it has S stereochemistry.

Conclusion

The structure of (S)-2-hydroxypropanal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 4

Answer 15

Interpretation Introduction

b) (S)-2-Hydroxypropanal

Interpretation:

The structure for (S)-2-hydroxypropanal is to be shown.

Concept introduction:

Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.

To show:

The structure for (S)-2-hydroxypropanal.

Answer 16

Expert Solution

Answer to Problem 54AP

The structure of (S)-2-hydroxypropanal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 3

Answer 17

Expert Solution

Answer 18

Expert Solution

Answer 19

Expert Solution

Answer 20

Explanation of Solution

The name indicates that the compound is an aldehyde with three carbon straight chain with a hydroxyl group attached to C₂. The molecule is chiral. The three groups, -OH(first highest priority), -CHO (second highest priority) and -CH₃(third highest priority) are arranged anticlockwise when viewed from the side away from H (fourth highest priority). Hence it has S stereochemistry.

Answer 21

Conclusion

The structure of (S)-2-hydroxypropanal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 4

Answer 22

Interpretation Introduction

c) 2-Methyl-3-heptanone

Interpretation:

The structure for 2-methyl-3-heptanone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for 2-methyl-3-heptanone.

Expert Solution

Answer to Problem 54AP

The structure of 2-methyl-3-heptanone is

Explanation of Solution

The name indicates that the compound is a ketone with seven carbon straight chain having the keto group at position three and a methyl group attached to C₂.

Conclusion

The structure of 2-methyl-3-heptanone is

Answer 23

Interpretation Introduction

c) 2-Methyl-3-heptanone

Interpretation:

The structure for 2-methyl-3-heptanone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for 2-methyl-3-heptanone.

Answer 24

Expert Solution

Answer to Problem 54AP

The structure of 2-methyl-3-heptanone is

Answer 25

Expert Solution

Answer 26

Expert Solution

Answer 27

Expert Solution

Answer 28

Explanation of Solution

The name indicates that the compound is a ketone with seven carbon straight chain having the keto group at position three and a methyl group attached to C₂.

Answer 29

Conclusion

The structure of 2-methyl-3-heptanone is

Answer 30

Interpretation Introduction

d) (2S,3R)-2,3,4-Trihydroxybutanal

Interpretation:

The structure for (2S,3R)-2,3,4-trihydroxybutanal is to be shown.

Concept introduction:

Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.

To show:

The structure for (2S,3R)-2,3,4-trihydroxybutanal.

Expert Solution

Answer to Problem 54AP

The structure of (2S,3R)-2,3,4-trihydroxybutanal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 5

Explanation of Solution

The name indicates that the compound is an aldehyde with four carbon straight chain and has three hydroxyl groups attached to C₂, C₃ and C₄.

The molecule is chiral. The C₂ is attached to the three groups, -OH(first highest priority), -CHO (second highest priority) and –C₃ (third highest priority) arranged anticlockwise when viewed from the side away from H (fourth highest priority). Hence it has S stereochemistry.

The C₃ is attached to the three groups, -OH(first highest priority), –C₂ (second highest priority) and –CH₂OH--(third highest priority) arranged clockwise when viewed from the side away from H (fourth highest priority). Hence it has R stereochemistry.

Conclusion

The structure of (2S,3R)-2,3,4-trihydroxybutanal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 6

Answer 31

Interpretation Introduction

d) (2S,3R)-2,3,4-Trihydroxybutanal

Interpretation:

The structure for (2S,3R)-2,3,4-trihydroxybutanal is to be shown.

Concept introduction:

Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.

To show:

The structure for (2S,3R)-2,3,4-trihydroxybutanal.

Answer 32

Expert Solution

Answer to Problem 54AP

The structure of (2S,3R)-2,3,4-trihydroxybutanal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 5

Answer 33

Expert Solution

Answer 34

Expert Solution

Answer 35

Expert Solution

Answer 36

Explanation of Solution

The name indicates that the compound is an aldehyde with four carbon straight chain and has three hydroxyl groups attached to C₂, C₃ and C₄.

The molecule is chiral. The C₂ is attached to the three groups, -OH(first highest priority), -CHO (second highest priority) and –C₃ (third highest priority) arranged anticlockwise when viewed from the side away from H (fourth highest priority). Hence it has S stereochemistry.

The C₃ is attached to the three groups, -OH(first highest priority), –C₂ (second highest priority) and –CH₂OH--(third highest priority) arranged clockwise when viewed from the side away from H (fourth highest priority). Hence it has R stereochemistry.

Answer 37

Conclusion

The structure of (2S,3R)-2,3,4-trihydroxybutanal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 6

Answer 38

Interpretation Introduction

e) 2,2,4,4-Tetramethyl-3-pentanone

Interpretation:

The structure for 2,2,4,4-tetramethyl-3-pentanone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for 2,2,4,4-tetramethyl-3-pentanone.

Expert Solution

Answer to Problem 54AP

The structure of 2,2,4,4-tetramethyl-3-pentanone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 7

Explanation of Solution

The name indicates that the compound is a ketone with five carbon straight chain with a keto group at position three attached to four methyl groups, two on C₂ and other two on C₄.

Conclusion

The structure of 2,2,4,4-Tetramethyl-3-pentanone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 8

Answer 39

Interpretation Introduction

e) 2,2,4,4-Tetramethyl-3-pentanone

Interpretation:

The structure for 2,2,4,4-tetramethyl-3-pentanone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for 2,2,4,4-tetramethyl-3-pentanone.

Answer 40

Expert Solution

Answer to Problem 54AP

The structure of 2,2,4,4-tetramethyl-3-pentanone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 7

Answer 41

Expert Solution

Answer 42

Expert Solution

Answer 43

Expert Solution

Answer 44

Explanation of Solution

The name indicates that the compound is a ketone with five carbon straight chain with a keto group at position three attached to four methyl groups, two on C₂ and other two on C₄.

Answer 45

Conclusion

The structure of 2,2,4,4-Tetramethyl-3-pentanone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 8

Answer 46

Interpretation Introduction

f) 4-methyl-3-penten-2-one

Interpretation:

The structure for 4-methyl-3-penten-2-one is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for 4-methyl-3-penten-2-one.

Expert Solution

Answer to Problem 54AP

The structure of 4-methyl-3-penten-2-one is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 9

Explanation of Solution

The name indicates that the compound is a ketone containing a five carbon straight chain, having a keto group at position two and a double bond between C₃ and C₄ with a methyl group on C₄.

Conclusion

The structure of 4-methyl-3-penten-2-one is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 10

Answer 47

Interpretation Introduction

f) 4-methyl-3-penten-2-one

Interpretation:

The structure for 4-methyl-3-penten-2-one is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for 4-methyl-3-penten-2-one.

Answer 48

Expert Solution

Answer to Problem 54AP

The structure of 4-methyl-3-penten-2-one is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 9

Answer 49

Expert Solution

Answer 50

Expert Solution

Answer 51

Expert Solution

Answer 52

Explanation of Solution

The name indicates that the compound is a ketone containing a five carbon straight chain, having a keto group at position two and a double bond between C₃ and C₄ with a methyl group on C₄.

Answer 53

Conclusion

The structure of 4-methyl-3-penten-2-one is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 10

Answer 54

Interpretation Introduction

g) Butanedial

Interpretation:

The structure for butanedial is to be shown.

Concept introduction:

Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.

To show:

The structure for butanedial.

Expert Solution

Answer to Problem 54AP

The structure of butanedial is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 11

Explanation of Solution

The name of the compound indicates that it has a four carbon straight chain with two aldehyde groups at both ends.

Conclusion

The structure of butanedial is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 12

Answer 55

Interpretation Introduction

g) Butanedial

Interpretation:

The structure for butanedial is to be shown.

Concept introduction:

Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.

To show:

The structure for butanedial.

Answer 56

Expert Solution

Answer to Problem 54AP

The structure of butanedial is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 11

Answer 57

Expert Solution

Answer 58

Expert Solution

Answer 59

Expert Solution

Answer 60

Explanation of Solution

The name of the compound indicates that it has a four carbon straight chain with two aldehyde groups at both ends.

Answer 61

Conclusion

The structure of butanedial is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 12

Answer 62

Interpretation Introduction

h) 3-Phenyl-2-propenal

Interpretation:

The structure for 3-phenyl-2-propenal is to be shown.

Concept introduction:

Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.

To show:

The structure for 3-phenyl-2-propenal.

Expert Solution

Answer to Problem 54AP

The structure of 3-phenyl-2-propenal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 13

Explanation of Solution

The name of the compound indicates that the compound is a three carbon aldehyde with a double bond between C₂ & C₃ and has a phenyl group attached to C₃.

Conclusion

The structure of 3-phenyl-2-propenal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 14

Answer 63

Interpretation Introduction

h) 3-Phenyl-2-propenal

Interpretation:

The structure for 3-phenyl-2-propenal is to be shown.

Concept introduction:

Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.

To show:

The structure for 3-phenyl-2-propenal.

Answer 64

Expert Solution

Answer to Problem 54AP

The structure of 3-phenyl-2-propenal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 13

Answer 65

Expert Solution

Answer 66

Expert Solution

Answer 67

Expert Solution

Answer 68

Explanation of Solution

The name of the compound indicates that the compound is a three carbon aldehyde with a double bond between C₂ & C₃ and has a phenyl group attached to C₃.

Answer 69

Conclusion

The structure of 3-phenyl-2-propenal is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 14

Answer 70

Interpretation Introduction

i) 6,6-Dimethyl-2,4-cyclohexadienone

Interpretation:

The structure for 6,6-dimethyl-2,4-cyclohexadienone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for 6,6-dimethyl-2,4-cyclohexadienone.

Expert Solution

Answer to Problem 54AP

The structure of 6,6-dimethyl-2,4-cyclohexadienone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 15

Explanation of Solution

The name of the compound indicates that it is a cyclic ketone with a cyclohexadiene ring containing two double bonds, one between C₂ & C₃ and other between C₄ & C₅. It also has two methyl groups on C₆.

Conclusion

The structure of 6,6-dimethyl-2,4-cyclohexadienone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 16

Answer 71

Interpretation Introduction

i) 6,6-Dimethyl-2,4-cyclohexadienone

Interpretation:

The structure for 6,6-dimethyl-2,4-cyclohexadienone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.

To show:

The structure for 6,6-dimethyl-2,4-cyclohexadienone.

Answer 72

Expert Solution

Answer to Problem 54AP

The structure of 6,6-dimethyl-2,4-cyclohexadienone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 15

Answer 73

Expert Solution

Answer 74

Expert Solution

Answer 75

Expert Solution

Answer 76

Explanation of Solution

The name of the compound indicates that it is a cyclic ketone with a cyclohexadiene ring containing two double bonds, one between C₂ & C₃ and other between C₄ & C₅. It also has two methyl groups on C₆.

Answer 77

Conclusion

The structure of 6,6-dimethyl-2,4-cyclohexadienone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 16

Answer 78

Interpretation Introduction

j) p-Nitroacetophenone

Interpretation:

The structure for p-nitroacetophenone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo. Some common names like acetophenone are retained by IUPAC.

To show:

The structure for p-nitroacetophenone.

Expert Solution

Answer to Problem 54AP

The structure of p-nitroacetophenone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 17

Explanation of Solution

The name of the compound indicates that it contains an actyl and nitro groups attached to a benzene ring in para relationship.

Conclusion

The structure of p-nitroacetophenone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 18

Answer 79

Interpretation Introduction

j) p-Nitroacetophenone

Interpretation:

The structure for p-nitroacetophenone is to be shown.

Concept introduction:

Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo. Some common names like acetophenone are retained by IUPAC.

To show:

The structure for p-nitroacetophenone.

Answer 80

Expert Solution

Answer to Problem 54AP

The structure of p-nitroacetophenone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 17

Answer 81

Expert Solution

Answer 82

Expert Solution

Answer 83

Expert Solution

Answer 84

Explanation of Solution

The name of the compound indicates that it contains an actyl and nitro groups attached to a benzene ring in para relationship.

Answer 85

Conclusion

The structure of p-nitroacetophenone is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 54AP , additional homework tip 18

Answer 86

Ch. 19.1 - Prob. 1P Ch. 19.1 - Draw structures corresponding to the following...Ch. 19.2 - Prob. 3P Ch. 19.2 - How would you carry out the following reactions?...Ch. 19.4 - Treatment of an aldehyde or ketone with cyanide...Ch. 19.4 - p-Nitrobenzaldehyde is more reactive toward...Ch. 19.5 - Prob. 7P Ch. 19.5 - The oxygen in water is primarily (99.8) 16O, but...Ch. 19.6 - Prob. 9P Ch. 19.8 - Show the products you would obtain by...

Concept explainers

Answer to Problem 54AP

Explanation of Solution

Answer to Problem 54AP

Explanation of Solution

Answer to Problem 54AP

Explanation of Solution

Answer to Problem 54AP

Explanation of Solution

Answer to Problem 54AP

Explanation of Solution

Answer to Problem 54AP

Explanation of Solution

Answer to Problem 54AP

Explanation of Solution

Answer to Problem 54AP

Explanation of Solution

Answer to Problem 54AP

Explanation of Solution

Answer to Problem 54AP

Explanation of Solution

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