Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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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
Check Mark

Answer to Problem 54AP

The structure of bromoacetone is

Organic Chemistry, 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

Organic Chemistry, 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
Check Mark

Answer to Problem 54AP

The structure of (S)-2-hydroxypropanal is

Organic Chemistry, 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

Organic Chemistry, 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
Check Mark

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
Check Mark

Answer to Problem 54AP

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

Organic Chemistry, 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

Organic Chemistry, 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
Check Mark

Answer to Problem 54AP

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

Organic Chemistry, 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

Organic Chemistry, 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
Check Mark

Answer to Problem 54AP

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

Organic Chemistry, 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

Organic Chemistry, 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
Check Mark

Answer to Problem 54AP

The structure of butanedial is

Organic Chemistry, 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

Organic Chemistry, 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
Check Mark

Answer to Problem 54AP

The structure of 3-phenyl-2-propenal is

Organic Chemistry, 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

Organic Chemistry, 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
Check Mark

Answer to Problem 54AP

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

Organic Chemistry, 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

Organic Chemistry, 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
Check Mark

Answer to Problem 54AP

The structure of p-nitroacetophenone is

Organic Chemistry, 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

Organic Chemistry, Chapter 19.SE, Problem 54AP , additional homework tip  18

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Chapter 19 Solutions

Organic Chemistry

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