Organic And Biological Chemistry
Organic And Biological Chemistry
7th Edition
ISBN: 9781305081079
Author: STOKER, H. Stephen (howard Stephen)
Publisher: Cengage Learning,
Question
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Chapter 5, Problem 5.46EP

(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 C−O bonds increase and/or number of C−H bonds decrease.

In organic chemistry, reduction reaction is referred to the number C−O bonds decrease and/or number of C−H 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 5.46EP

The structural formula of the expected product is,

Organic And Biological Chemistry, Chapter 5, Problem 5.46EP , 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,

Organic And Biological Chemistry, Chapter 5, Problem 5.46EP , additional homework tip 2

Given substance is,

Organic And Biological Chemistry, Chapter 5, Problem 5.46EP , 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,

Organic And Biological Chemistry, Chapter 5, Problem 5.46EP , 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,

Organic And Biological Chemistry, Chapter 5, Problem 5.46EP , 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 C−O bonds increase and/or number of C−H bonds decrease.

In organic chemistry, reduction reaction is referred to the number C−O bonds decrease and/or number of C−H 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 5.46EP

The structural formula of the expected product is,

Organic And Biological Chemistry, Chapter 5, Problem 5.46EP , 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,

Organic And Biological Chemistry, Chapter 5, Problem 5.46EP , additional homework tip 7

Given substance is,

Organic And Biological Chemistry, Chapter 5, Problem 5.46EP , 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,

Organic And Biological Chemistry, Chapter 5, Problem 5.46EP , 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,

Organic And Biological Chemistry, Chapter 5, Problem 5.46EP , 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 C−O bonds increase and/or number of C−H bonds decrease.

In organic chemistry, reduction reaction is referred to the number C−O bonds decrease and/or number of C−H 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 5.46EP

The structural formula of the expected product is,

Organic And Biological Chemistry, Chapter 5, Problem 5.46EP , 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,

Organic And Biological Chemistry, Chapter 5, Problem 5.46EP , additional homework tip 12

Given substance is,

Organic And Biological Chemistry, Chapter 5, Problem 5.46EP , 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,

Organic And Biological Chemistry, Chapter 5, Problem 5.46EP , 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,

Organic And Biological Chemistry, Chapter 5, Problem 5.46EP , 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 C−O bonds increase and/or number of C−H bonds decrease.

In organic chemistry, reduction reaction is referred to the number C−O bonds decrease and/or number of C−H 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 5.46EP

The structural formula of the expected product is,

Organic And Biological Chemistry, Chapter 5, Problem 5.46EP , additional homework tip 16

Explanation of Solution

Given substance is,

Organic And Biological Chemistry, Chapter 5, Problem 5.46EP , 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,

Organic And Biological Chemistry, Chapter 5, Problem 5.46EP , 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 5 Solutions

Organic And Biological Chemistry

Ch. 5.1 - Prob. 1QQCh. 5.1 - Prob. 2QQCh. 5.1 - Prob. 3QQCh. 5.1 - Prob. 4QQCh. 5.1 - Prob. 5QQCh. 5.2 - Prob. 1QQCh. 5.2 - Prob. 2QQCh. 5.2 - Prob. 3QQCh. 5.2 - Prob. 4QQCh. 5.2 - Prob. 5QQ
Ch. 5.3 - Prob. 1QQCh. 5.3 - Prob. 2QQCh. 5.3 - Prob. 3QQCh. 5.4 - Prob. 1QQCh. 5.4 - Prob. 2QQCh. 5.4 - Prob. 3QQCh. 5.5 - Prob. 1QQCh. 5.5 - Prob. 2QQCh. 5.5 - Prob. 3QQCh. 5.6 - Prob. 1QQCh. 5.6 - Prob. 2QQCh. 5.7 - Which of the following statements about acid...Ch. 5.7 - Prob. 2QQCh. 5.7 - Prob. 3QQCh. 5.8 - Prob. 1QQCh. 5.8 - Prob. 2QQCh. 5.8 - Prob. 3QQCh. 5.8 - Prob. 4QQCh. 5.9 - Prob. 1QQCh. 5.9 - Prob. 2QQCh. 5.10 - Prob. 1QQCh. 5.10 - Prob. 2QQCh. 5.11 - Prob. 1QQCh. 5.11 - Prob. 2QQCh. 5.11 - Prob. 3QQCh. 5.12 - Prob. 1QQCh. 5.12 - Prob. 2QQCh. 5.12 - Prob. 3QQCh. 5.12 - Prob. 4QQCh. 5.13 - Prob. 1QQCh. 5.13 - Prob. 2QQCh. 5.14 - Prob. 1QQCh. 5.14 - Prob. 2QQCh. 5.14 - Prob. 3QQCh. 5.15 - Prob. 1QQCh. 5.15 - Prob. 2QQCh. 5.15 - Prob. 3QQCh. 5.16 - Prob. 1QQCh. 5.16 - Prob. 2QQCh. 5.16 - Prob. 3QQCh. 5.17 - Prob. 1QQCh. 5.17 - Prob. 2QQCh. 5.18 - Prob. 1QQCh. 5.18 - Prob. 2QQCh. 5.18 - Prob. 3QQCh. 5.19 - Prob. 1QQCh. 5.19 - Prob. 2QQCh. 5.19 - Prob. 3QQCh. 5.19 - Prob. 4QQCh. 5.20 - Prob. 1QQCh. 5.20 - Prob. 2QQCh. 5.20 - Prob. 3QQCh. 5.20 - Prob. 4QQCh. 5 - Prob. 5.1EPCh. 5 - Prob. 5.2EPCh. 5 - Prob. 5.3EPCh. 5 - Indicate whether or not each of the compounds in...Ch. 5 - Prob. 5.5EPCh. 5 - Prob. 5.6EPCh. 5 - Prob. 5.7EPCh. 5 - Prob. 5.8EPCh. 5 - Prob. 5.9EPCh. 5 - Prob. 5.10EPCh. 5 - Prob. 5.11EPCh. 5 - Prob. 5.12EPCh. 5 - Prob. 5.13EPCh. 5 - Prob. 5.14EPCh. 5 - Prob. 5.15EPCh. 5 - Assign an IUPAC name to each of the following...Ch. 5 - Prob. 5.17EPCh. 5 - Prob. 5.18EPCh. 5 - Prob. 5.19EPCh. 5 - Prob. 5.20EPCh. 5 - Prob. 5.21EPCh. 5 - Prob. 5.22EPCh. 5 - Prob. 5.23EPCh. 5 - Prob. 5.24EPCh. 5 - Prob. 5.25EPCh. 5 - Prob. 5.26EPCh. 5 - Prob. 5.27EPCh. 5 - Prob. 5.28EPCh. 5 - Prob. 5.29EPCh. 5 - Prob. 5.30EPCh. 5 - Prob. 5.31EPCh. 5 - Prob. 5.32EPCh. 5 - Prob. 5.33EPCh. 5 - Prob. 5.34EPCh. 5 - Prob. 5.35EPCh. 5 - Prob. 5.36EPCh. 5 - Prob. 5.37EPCh. 5 - Prob. 5.38EPCh. 5 - Prob. 5.39EPCh. 5 - Prob. 5.40EPCh. 5 - Determine the maximum number of hydrogen bonds...Ch. 5 - Prob. 5.42EPCh. 5 - Prob. 5.43EPCh. 5 - Prob. 5.44EPCh. 5 - Prob. 5.45EPCh. 5 - Prob. 5.46EPCh. 5 - Prob. 5.47EPCh. 5 - Prob. 5.48EPCh. 5 - Prob. 5.49EPCh. 5 - Prob. 5.50EPCh. 5 - Prob. 5.51EPCh. 5 - Prob. 5.52EPCh. 5 - Prob. 5.53EPCh. 5 - Prob. 5.54EPCh. 5 - Draw structural formulas for the following...Ch. 5 - Prob. 5.56EPCh. 5 - Give the IUPAC name for each of the following...Ch. 5 - Give the IUPAC name for each of the following...Ch. 5 - Prob. 5.59EPCh. 5 - Prob. 5.60EPCh. 5 - Prob. 5.61EPCh. 5 - Prob. 5.62EPCh. 5 - Prob. 5.63EPCh. 5 - Prob. 5.64EPCh. 5 - Prob. 5.65EPCh. 5 - Which three carboxylic acids have salts that are...Ch. 5 - Prob. 5.67EPCh. 5 - Which carboxylic acid has salts that are used to...Ch. 5 - Prob. 5.69EPCh. 5 - Prob. 5.70EPCh. 5 - Prob. 5.71EPCh. 5 - Prob. 5.72EPCh. 5 - Prob. 5.73EPCh. 5 - Prob. 5.74EPCh. 5 - Prob. 5.75EPCh. 5 - Prob. 5.76EPCh. 5 - Prob. 5.77EPCh. 5 - Prob. 5.78EPCh. 5 - Prob. 5.79EPCh. 5 - Prob. 5.80EPCh. 5 - Prob. 5.81EPCh. 5 - Prob. 5.82EPCh. 5 - Prob. 5.83EPCh. 5 - Prob. 5.84EPCh. 5 - Prob. 5.85EPCh. 5 - Prob. 5.86EPCh. 5 - Prob. 5.87EPCh. 5 - Prob. 5.88EPCh. 5 - Prob. 5.89EPCh. 5 - Prob. 5.90EPCh. 5 - Assign common names to each of the esters in...Ch. 5 - Prob. 5.92EPCh. 5 - Prob. 5.93EPCh. 5 - Assign an IUPAC name to each of the following...Ch. 5 - Draw a structural formula for each of the...Ch. 5 - Prob. 5.96EPCh. 5 - Prob. 5.97EPCh. 5 - Prob. 5.98EPCh. 5 - Prob. 5.99EPCh. 5 - Prob. 5.100EPCh. 5 - Prob. 5.101EPCh. 5 - How many carbon atoms are present in a molecule of...Ch. 5 - Prob. 5.103EPCh. 5 - Prob. 5.104EPCh. 5 - Prob. 5.105EPCh. 5 - Prob. 5.106EPCh. 5 - Prob. 5.107EPCh. 5 - Prob. 5.108EPCh. 5 - Prob. 5.109EPCh. 5 - Prob. 5.110EPCh. 5 - Prob. 5.111EPCh. 5 - Prob. 5.112EPCh. 5 - Prob. 5.113EPCh. 5 - Prob. 5.114EPCh. 5 - Prob. 5.115EPCh. 5 - Prob. 5.116EPCh. 5 - Prob. 5.117EPCh. 5 - Prob. 5.118EPCh. 5 - Prob. 5.119EPCh. 5 - Prob. 5.120EPCh. 5 - Prob. 5.121EPCh. 5 - Prob. 5.122EPCh. 5 - Prob. 5.123EPCh. 5 - Prob. 5.124EPCh. 5 - Write the structural formulas of the reaction...Ch. 5 - Prob. 5.126EPCh. 5 - Prob. 5.127EPCh. 5 - Prob. 5.128EPCh. 5 - Prob. 5.129EPCh. 5 - Prob. 5.130EPCh. 5 - Prob. 5.131EPCh. 5 - Prob. 5.132EPCh. 5 - Prob. 5.133EPCh. 5 - Prob. 5.134EPCh. 5 - Prob. 5.135EPCh. 5 - Prob. 5.136EPCh. 5 - Prob. 5.137EPCh. 5 - Prob. 5.138EPCh. 5 - Prob. 5.139EPCh. 5 - Prob. 5.140EPCh. 5 - Prob. 5.141EPCh. 5 - Prob. 5.142EPCh. 5 - Prob. 5.143EPCh. 5 - Prob. 5.144EPCh. 5 - Prob. 5.145EPCh. 5 - Prob. 5.146EPCh. 5 - Prob. 5.147EPCh. 5 - Prob. 5.148EPCh. 5 - Draw a condensed structural formula for the...Ch. 5 - Draw a condensed structural formula for the...Ch. 5 - Prob. 5.151EPCh. 5 - Prob. 5.152EPCh. 5 - Prob. 5.153EPCh. 5 - Prob. 5.154EPCh. 5 - Prob. 5.155EPCh. 5 - Prob. 5.156EPCh. 5 - Prob. 5.157EPCh. 5 - Prob. 5.158EPCh. 5 - Prob. 5.159EPCh. 5 - Prob. 5.160EPCh. 5 - Prob. 5.161EPCh. 5 - Prob. 5.162EPCh. 5 - Prob. 5.163EPCh. 5 - Prob. 5.164EP
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