Question

Question: What alcohol can be oxidized to each carboxylic acid?

a.

b.

c.

Short answer

Answer

a.

Starting material for acid (a)

b.

Starting material for acid (b)

c.

Starting material for acid (c)

Step-by-step solution

Step-by-Step Solution Step 1: Preparation of carboxylic acid

Oxidation reactions generally prepare carboxylic acids because the carbon in the carboxyl group is highly oxidized with three C-O bonds.

Alcohols undergo direct oxidation to carboxylic acids in the presence of strong oxidizing agents.

Benzoic acid is prepared by the oxidation of alkylbenzenes using potassium permanganate.

Ozonolysis can also be used for the preparation of acids from alkynes.

Oxidation of alcohols

Alcohols on oxidation get converted into carbonyl compounds, which on further oxidation form carboxylic acids.

But when strong oxidizing agents are used, primary alcohols can be directly converted into carboxylic acid by over oxidation.

The oxidizing agents used for this reaction are sodium dichromate, potassium dichromate, or chromium trioxide in the presence of water and sulfuric acid.

Identifying alcohols used for the preparation of given acids

The starting material required to synthesize the given carboxylic acid is the primary alcohol with the same number of carbon atoms. The retrosynthesis is shown below:

a.

Retro analysis of acid (a)

b.

Retro analysis of acid (b)

c.

Retro analysis of acid (c)