General, Organic, and Biological Chemistry Seventh Edition
General, Organic, and Biological Chemistry Seventh Edition
7th Edition
ISBN: 9781305767867
Author: H. Stephan Stoker
Publisher: Cengage Learning
Question
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Chapter 16, Problem 16.46EP

(a)

Interpretation Introduction

Interpretation:

The structural formula for carboxylic acid that is expected to be formed on oxidation of the given substance has to be drawn.

Concept Introduction:

In organic chemistry, oxidation reaction is referred to the number CO bonds increase and/or number of CH bonds decrease.

In organic chemistry, reduction reaction is referred to the number CO bonds decrease and/or number of CH bonds increase.

Alcohols undergo oxidation reaction and reduction reaction.  This depends upon the number of hydrogen atoms that is bonded to the alpha carbon atom.  Primary and secondary alcohol undergoes oxidation reaction while tertiary alcohol does not undergo oxidation reaction.  Primary alcohols undergo oxidation to give aldehyde and carboxylic acid as product.  Secondary alcohol undergoes oxidation to give ketone as the product.

Aldehyde undergoes oxidation to give carboxylic acid as the product while ketone does not undergo oxidation reaction.

Aromatic carboxylic acids are prepared from alkyl substituted benzenes.

(a)

Expert Solution
Check Mark

Answer to Problem 16.46EP

The structural formula of the expected product is,

General, Organic, and Biological Chemistry Seventh Edition, Chapter 16, Problem 16.46EP , additional homework tip  1

Explanation of Solution

Aldehyde on oxidation gives carboxylic acid as the product.  The general scheme can be represented as shown below,

General, Organic, and Biological Chemistry Seventh Edition, Chapter 16, Problem 16.46EP , additional homework tip  2

Given substance is,

General, Organic, and Biological Chemistry Seventh Edition, Chapter 16, Problem 16.46EP , additional homework tip  3

The given compound is propanal and it is an aldehyde.  Propanal on oxidation gives propanoic acid as the product.  The complete scheme can be represented as shown below,

General, Organic, and Biological Chemistry Seventh Edition, Chapter 16, Problem 16.46EP , additional homework tip  4

The carboxylic acid that is formed on oxidation of the given substance is propanoic acid.  The structural formula of propanoic acid is given below,

General, Organic, and Biological Chemistry Seventh Edition, Chapter 16, Problem 16.46EP , additional homework tip  5

Conclusion

Structural formula of the carboxylic acid formed by the oxidation of given substance is drawn.

(b)

Interpretation Introduction

Interpretation:

The structural formula for carboxylic acid that is expected to be formed on oxidation of the given substance has to be drawn.

Concept Introduction:

In organic chemistry, oxidation reaction is referred to the number CO bonds increase and/or number of CH bonds decrease.

In organic chemistry, reduction reaction is referred to the number CO bonds decrease and/or number of CH bonds increase.

Alcohols undergo oxidation reaction and reduction reaction.  This depends upon the number of hydrogen atoms that is bonded to the alpha carbon atom.  Primary and secondary alcohol undergoes oxidation reaction while tertiary alcohol does not undergo oxidation reaction.  Primary alcohols undergo oxidation to give aldehyde and carboxylic acid as product.  Secondary alcohol undergoes oxidation to give ketone as the product.

Aldehyde undergoes oxidation to give carboxylic acid as the product while ketone does not undergo oxidation reaction.

Aromatic carboxylic acids are prepared from alkyl substituted benzenes.

(b)

Expert Solution
Check Mark

Answer to Problem 16.46EP

The structural formula of the expected product is,

General, Organic, and Biological Chemistry Seventh Edition, Chapter 16, Problem 16.46EP , additional homework tip  6

Explanation of Solution

Primary alcohol on oxidation gives aldehyde as intermediate product.  This on further oxidation gives carboxylic acid as the product.  The general scheme can be represented as shown below,

General, Organic, and Biological Chemistry Seventh Edition, Chapter 16, Problem 16.46EP , additional homework tip  7

Given substance is,

General, Organic, and Biological Chemistry Seventh Edition, Chapter 16, Problem 16.46EP , additional homework tip  8

This is a primary alcohol.  The given compound is propanol.  Propanol on oxidation gives propanal as the intermediate product.  The formed propanal on oxidation gives propanoic acid as the product.  The complete scheme can be represented as shown below,

General, Organic, and Biological Chemistry Seventh Edition, Chapter 16, Problem 16.46EP , additional homework tip  9

The carboxylic acid that is formed on oxidation of the given substance is propanoic acid.  The structural formula of propanoic acid is given below,

General, Organic, and Biological Chemistry Seventh Edition, Chapter 16, Problem 16.46EP , additional homework tip  10

Conclusion

Structural formula of the carboxylic acid formed by the oxidation of given substance is drawn.

(c)

Interpretation Introduction

Interpretation:

The structural formula for carboxylic acid that is expected to be formed on oxidation of the given substance has to be drawn.

Concept Introduction:

In organic chemistry, oxidation reaction is referred to the number CO bonds increase and/or number of CH bonds decrease.

In organic chemistry, reduction reaction is referred to the number CO bonds decrease and/or number of CH bonds increase.

Alcohols undergo oxidation reaction and reduction reaction.  This depends upon the number of hydrogen atoms that is bonded to the alpha carbon atom.  Primary and secondary alcohol undergoes oxidation reaction while tertiary alcohol does not undergo oxidation reaction.  Primary alcohols undergo oxidation to give aldehyde and carboxylic acid as product.  Secondary alcohol undergoes oxidation to give ketone as the product.

Aldehyde undergoes oxidation to give carboxylic acid as the product while ketone does not undergo oxidation reaction.

Aromatic carboxylic acids are prepared from alkyl substituted benzenes.

(c)

Expert Solution
Check Mark

Answer to Problem 16.46EP

The structural formula of the expected product is,

General, Organic, and Biological Chemistry Seventh Edition, Chapter 16, Problem 16.46EP , additional homework tip  11

Explanation of Solution

Aldehyde on oxidation gives carboxylic acid as the product.  The general scheme can be represented as shown below,

General, Organic, and Biological Chemistry Seventh Edition, Chapter 16, Problem 16.46EP , additional homework tip  12

Given substance is,

General, Organic, and Biological Chemistry Seventh Edition, Chapter 16, Problem 16.46EP , additional homework tip  13

The given compound is 2,3-dimethylbutanal and it is an aldehyde.  2,3-dimethylbutanal on oxidation gives 2,3-dimethylbutanoic acid as the product.  The complete scheme can be represented as shown below,

General, Organic, and Biological Chemistry Seventh Edition, Chapter 16, Problem 16.46EP , additional homework tip  14

The carboxylic acid that is formed on oxidation of the given substance is 2,3-dimethylbutanoic acid.  The structural formula of 2,3-dimethylbutanoic acid is given below,

General, Organic, and Biological Chemistry Seventh Edition, Chapter 16, Problem 16.46EP , additional homework tip  15

Conclusion

Structural formula of the carboxylic acid formed by the oxidation of given substance is drawn.

(d)

Interpretation Introduction

Interpretation:

The structural formula for carboxylic acid that is expected to be formed on oxidation of the given substance has to be drawn.

Concept Introduction:

In organic chemistry, oxidation reaction is referred to the number CO bonds increase and/or number of CH bonds decrease.

In organic chemistry, reduction reaction is referred to the number CO bonds decrease and/or number of CH bonds increase.

Alcohols undergo oxidation reaction and reduction reaction.  This depends upon the number of hydrogen atoms that is bonded to the alpha carbon atom.  Primary and secondary alcohol undergoes oxidation reaction while tertiary alcohol does not undergo oxidation reaction.  Primary alcohols undergo oxidation to give aldehyde and carboxylic acid as product.  Secondary alcohol undergoes oxidation to give ketone as the product.

Aldehyde undergoes oxidation to give carboxylic acid as the product while ketone does not undergo oxidation reaction.

Aromatic carboxylic acids are prepared from alkyl substituted benzenes.

(d)

Expert Solution
Check Mark

Answer to Problem 16.46EP

The structural formula of the expected product is,

General, Organic, and Biological Chemistry Seventh Edition, Chapter 16, Problem 16.46EP , additional homework tip  16

Explanation of Solution

Given substance is,

General, Organic, and Biological Chemistry Seventh Edition, Chapter 16, Problem 16.46EP , additional homework tip  17

Oxidation of the alkyl side chain in a benzene derivative leads to the formation of aromatic acids.  All the carbon atoms in alkyl group are lost except the one that is attached to the ring.  The one carbon that is attached to the ring becomes a part of carboxyl functional group.  This can be depicted as shown below,

General, Organic, and Biological Chemistry Seventh Edition, Chapter 16, Problem 16.46EP , additional homework tip  18

The product formed is benzoic acid.

Conclusion

Structural formula of the carboxylic acid formed by the oxidation of given substance is drawn.

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Chapter 16 Solutions

General, Organic, and Biological Chemistry Seventh Edition

Ch. 16.3 - Prob. 1QQCh. 16.3 - Prob. 2QQCh. 16.3 - Prob. 3QQCh. 16.4 - Prob. 1QQCh. 16.4 - Prob. 2QQCh. 16.4 - Prob. 3QQCh. 16.5 - Prob. 1QQCh. 16.5 - Prob. 2QQCh. 16.5 - Prob. 3QQCh. 16.6 - Prob. 1QQCh. 16.6 - Prob. 2QQCh. 16.7 - Prob. 1QQCh. 16.7 - Prob. 2QQCh. 16.7 - Prob. 3QQCh. 16.8 - Prob. 1QQCh. 16.8 - Prob. 2QQCh. 16.8 - Prob. 3QQCh. 16.8 - Prob. 4QQCh. 16.9 - Prob. 1QQCh. 16.9 - Prob. 2QQCh. 16.10 - Prob. 1QQCh. 16.10 - Prob. 2QQCh. 16.11 - Prob. 1QQCh. 16.11 - Prob. 2QQCh. 16.11 - Prob. 3QQCh. 16.12 - Prob. 1QQCh. 16.12 - Prob. 2QQCh. 16.12 - Prob. 3QQCh. 16.12 - Prob. 4QQCh. 16.13 - Prob. 1QQCh. 16.13 - Prob. 2QQCh. 16.14 - Prob. 1QQCh. 16.14 - Prob. 2QQCh. 16.14 - Prob. 3QQCh. 16.15 - Prob. 1QQCh. 16.15 - Prob. 2QQCh. 16.15 - Prob. 3QQCh. 16.16 - Prob. 1QQCh. 16.16 - Prob. 2QQCh. 16.16 - Prob. 3QQCh. 16.17 - Prob. 1QQCh. 16.17 - Prob. 2QQCh. 16.18 - Prob. 1QQCh. 16.18 - Prob. 2QQCh. 16.18 - Prob. 3QQCh. 16.19 - Prob. 1QQCh. 16.19 - Prob. 2QQCh. 16.19 - Prob. 3QQCh. 16.19 - Prob. 4QQCh. 16.20 - Prob. 1QQCh. 16.20 - Prob. 2QQCh. 16.20 - Prob. 3QQCh. 16.20 - Prob. 4QQCh. 16 - Prob. 16.1EPCh. 16 - Prob. 16.2EPCh. 16 - Prob. 16.3EPCh. 16 - Prob. 16.4EPCh. 16 - Prob. 16.5EPCh. 16 - Prob. 16.6EPCh. 16 - Prob. 16.7EPCh. 16 - Prob. 16.8EPCh. 16 - Prob. 16.9EPCh. 16 - Prob. 16.10EPCh. 16 - Prob. 16.11EPCh. 16 - Prob. 16.12EPCh. 16 - Prob. 16.13EPCh. 16 - Prob. 16.14EPCh. 16 - Prob. 16.15EPCh. 16 - Prob. 16.16EPCh. 16 - Prob. 16.17EPCh. 16 - Prob. 16.18EPCh. 16 - Prob. 16.19EPCh. 16 - Prob. 16.20EPCh. 16 - Prob. 16.21EPCh. 16 - Prob. 16.22EPCh. 16 - Prob. 16.23EPCh. 16 - Prob. 16.24EPCh. 16 - Prob. 16.25EPCh. 16 - Prob. 16.26EPCh. 16 - Prob. 16.27EPCh. 16 - Prob. 16.28EPCh. 16 - Prob. 16.29EPCh. 16 - Prob. 16.30EPCh. 16 - Prob. 16.31EPCh. 16 - Prob. 16.32EPCh. 16 - Prob. 16.33EPCh. 16 - Prob. 16.34EPCh. 16 - Prob. 16.35EPCh. 16 - Prob. 16.36EPCh. 16 - Prob. 16.37EPCh. 16 - Prob. 16.38EPCh. 16 - Prob. 16.39EPCh. 16 - Prob. 16.40EPCh. 16 - Determine the maximum number of hydrogen bonds...Ch. 16 - Prob. 16.42EPCh. 16 - Prob. 16.43EPCh. 16 - Prob. 16.44EPCh. 16 - Prob. 16.45EPCh. 16 - Prob. 16.46EPCh. 16 - Prob. 16.47EPCh. 16 - Prob. 16.48EPCh. 16 - Prob. 16.49EPCh. 16 - Prob. 16.50EPCh. 16 - Prob. 16.51EPCh. 16 - Prob. 16.52EPCh. 16 - Prob. 16.53EPCh. 16 - Prob. 16.54EPCh. 16 - Prob. 16.55EPCh. 16 - Prob. 16.56EPCh. 16 - Give the IUPAC name for each of the following...Ch. 16 - Give the IUPAC name for each of the following...Ch. 16 - Prob. 16.59EPCh. 16 - Give the common name for each of the carboxylic...Ch. 16 - Prob. 16.61EPCh. 16 - Write a chemical equation for the preparation of...Ch. 16 - Prob. 16.63EPCh. 16 - Prob. 16.64EPCh. 16 - Prob. 16.65EPCh. 16 - Prob. 16.66EPCh. 16 - Prob. 16.67EPCh. 16 - Prob. 16.68EPCh. 16 - Prob. 16.69EPCh. 16 - Prob. 16.70EPCh. 16 - Prob. 16.71EPCh. 16 - Prob. 16.72EPCh. 16 - Prob. 16.73EPCh. 16 - Prob. 16.74EPCh. 16 - Prob. 16.75EPCh. 16 - Prob. 16.76EPCh. 16 - Prob. 16.77EPCh. 16 - Prob. 16.78EPCh. 16 - Prob. 16.79EPCh. 16 - Prob. 16.80EPCh. 16 - Prob. 16.81EPCh. 16 - Prob. 16.82EPCh. 16 - Prob. 16.83EPCh. 16 - Prob. 16.84EPCh. 16 - Prob. 16.85EPCh. 16 - Prob. 16.86EPCh. 16 - Prob. 16.87EPCh. 16 - Prob. 16.88EPCh. 16 - Prob. 16.89EPCh. 16 - Prob. 16.90EPCh. 16 - Prob. 16.91EPCh. 16 - Prob. 16.92EPCh. 16 - Assign an IUPAC name to each of the following...Ch. 16 - Prob. 16.94EPCh. 16 - Prob. 16.95EPCh. 16 - Prob. 16.96EPCh. 16 - Prob. 16.97EPCh. 16 - Prob. 16.98EPCh. 16 - Prob. 16.99EPCh. 16 - Prob. 16.100EPCh. 16 - How many carbon atoms are present in a molecule of...Ch. 16 - Prob. 16.102EPCh. 16 - Prob. 16.103EPCh. 16 - Prob. 16.104EPCh. 16 - Prob. 16.105EPCh. 16 - Prob. 16.106EPCh. 16 - Prob. 16.107EPCh. 16 - Prob. 16.108EPCh. 16 - Prob. 16.109EPCh. 16 - Prob. 16.110EPCh. 16 - Prob. 16.111EPCh. 16 - Prob. 16.112EPCh. 16 - Prob. 16.113EPCh. 16 - Prob. 16.114EPCh. 16 - Prob. 16.115EPCh. 16 - Prob. 16.116EPCh. 16 - Prob. 16.117EPCh. 16 - Prob. 16.118EPCh. 16 - Prob. 16.119EPCh. 16 - Prob. 16.120EPCh. 16 - Prob. 16.121EPCh. 16 - Prob. 16.122EPCh. 16 - Prob. 16.123EPCh. 16 - Prob. 16.124EPCh. 16 - Prob. 16.125EPCh. 16 - Prob. 16.126EPCh. 16 - Prob. 16.127EPCh. 16 - Prob. 16.128EPCh. 16 - Prob. 16.129EPCh. 16 - Prob. 16.130EPCh. 16 - Prob. 16.131EPCh. 16 - Prob. 16.132EPCh. 16 - Prob. 16.133EPCh. 16 - Prob. 16.134EPCh. 16 - Prob. 16.135EPCh. 16 - Prob. 16.136EPCh. 16 - Prob. 16.137EPCh. 16 - Prob. 16.138EPCh. 16 - Prob. 16.139EPCh. 16 - Prob. 16.140EPCh. 16 - Prob. 16.141EPCh. 16 - Prob. 16.142EPCh. 16 - Prob. 16.143EPCh. 16 - Prob. 16.144EPCh. 16 - Prob. 16.145EPCh. 16 - Prob. 16.146EPCh. 16 - Prob. 16.147EPCh. 16 - Prob. 16.148EPCh. 16 - Draw a condensed structural formula for the...Ch. 16 - Prob. 16.150EPCh. 16 - Prob. 16.151EPCh. 16 - Prob. 16.152EPCh. 16 - Prob. 16.153EPCh. 16 - Prob. 16.154EPCh. 16 - Prob. 16.155EPCh. 16 - Prob. 16.156EPCh. 16 - Prob. 16.157EPCh. 16 - Prob. 16.158EPCh. 16 - Prob. 16.159EPCh. 16 - Prob. 16.160EPCh. 16 - Prob. 16.161EPCh. 16 - Prob. 16.162EPCh. 16 - Prob. 16.163EPCh. 16 - Prob. 16.164EP
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