Chapter 5, Problem 5.45EP

(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 $\text{C}-\text{O}$ bonds increase and/or number of $\text{C}-\text{H}$ bonds decrease.

In organic chemistry, reduction reaction is referred to the number $\text{C}-\text{O}$ bonds decrease and/or number of $\text{C}-\text{H}$ 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.

Answer to Problem 5.45EP

The structural formula of the expected product is,

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,

Given substance is,

This is a primary alcohol.  The given compound is ethanol.  Ethanol on oxidation gives ethanal as the intermediate product.  The formed ethanal on oxidation gives ethanoic acid as the product.  The complete scheme can be represented as shown below,

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

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 $\text{C}-\text{O}$ bonds increase and/or number of $\text{C}-\text{H}$ bonds decrease.

In organic chemistry, reduction reaction is referred to the number $\text{C}-\text{O}$ bonds decrease and/or number of $\text{C}-\text{H}$ 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.

Answer to Problem 5.45EP

The structural formula of the expected product is,

Explanation of Solution

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

Given substance is,

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

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

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 $\text{C}-\text{O}$ bonds increase and/or number of $\text{C}-\text{H}$ bonds decrease.

In organic chemistry, reduction reaction is referred to the number $\text{C}-\text{O}$ bonds decrease and/or number of $\text{C}-\text{H}$ 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.

Answer to Problem 5.45EP

The structural formula of the expected product is,

Explanation of Solution

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

Given substance is,

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

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

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 $\text{C}-\text{O}$ bonds increase and/or number of $\text{C}-\text{H}$ bonds decrease.

In organic chemistry, reduction reaction is referred to the number $\text{C}-\text{O}$ bonds decrease and/or number of $\text{C}-\text{H}$ 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.

Answer to Problem 5.45EP

The structural formula of the expected product is,

Explanation of Solution

Given substance is,

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,

The product formed is benzoic acid.

Conclusion

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