Q. 12.30 - An Introduction to General, Organic, and Biological Chemistry

Question

Draw the condensed structural or line-angle formula for the aldehyde or ketone formed when each of the following alcohols is oxidized [O] (if no reaction, write none): 

Step-by-Step Solution

Answer

a. $2-\mathrm{Methylpropanal}$

b. None

c. Cyclobutanone 

d. $4-\mathrm{Methylpentane}-2-\mathrm{one}$

Part(a) Step 1: Given information

We need to draw the condensed structural or line-angle formula for the aldehyde or ketone formed when following alcohol is oxidized: 

${\mathrm{CH}}_3-\mathrm{CH}\left({\mathrm{CH}}_3\right)-{\mathrm{CH}}_2-\mathrm{OH} (2-\mathrm{Methyl}-\mathrm{propanol})$

Part(a) Step 2: Explanation

Alcohols are converted to aldehydes and ketones during the oxidation process. This is one of the most crucial reactions in organic chemistry. When primary alcohols are oxidised, aldehydes and carboxylic acids are generated; when secondary alcohols are oxidised, ketones are formed. Tertiary alcohols, on the other hand, can't be oxidised without destroying the molecule's C–C bonds.

Given, ${\mathrm{CH}}_3-\mathrm{CH}\left({\mathrm{CH}}_3\right)-{\mathrm{CH}}_2-\mathrm{OH} (2-\mathrm{Methyl}-\mathrm{propane}-1-\mathrm{ol})$ is a primary alcohol. Hence, it is oxidized to ${\mathrm{CH}}_3-\mathrm{CH}\left({\mathrm{CH}}_3\right)-\mathrm{CHO} (2-\mathrm{Methyl}-\mathrm{propanal})$.

Part(b) Step 1: Given information

We need to draw the condensed structural or line-angle formula for the aldehyde or ketone formed when following alcohol is oxidized: 

${\mathrm{CH}}_3-{\mathrm{CH}}_2-\mathrm{C}\left({\mathrm{CH}}_3\right)\mathrm{OH}-{\mathrm{CH}}_3$

Part(b) Step 2: Explanation

When primary alcohols are oxidized, aldehydes and carboxylic acids are generated; when secondary alcohols are oxidized, ketones are formed. Tertiary alcohols, on the other hand, can't be oxidized without destroying the molecule's C–C bonds.

Given, ${\mathrm{CH}}_3-{\mathrm{CH}}_2-\mathrm{C}\left({\mathrm{CH}}_3\right)\mathrm{OH}-{\mathrm{CH}}_3 (2-\mathrm{Methyl}-\mathrm{butane}-2-\mathrm{ol})$ is a tertiary alcohol. Hence, no oxidation will take place.

Part(c) Step 1: Given information

We need to draw the condensed structural or line-angle formula for the aldehyde or ketone formed when following alcohol is oxidized: 

Part(c) Step 2: Explanation

When primary alcohols are oxidized, aldehydes and carboxylic acids are generated; when secondary alcohols are oxidized, ketones are formed. Tertiary alcohols, on the other hand, can't be oxidized without destroying the molecule's C–C bonds.

Given, Cyclobutanol is a secondary alcohol. Hence, it is oxidized to Cyclobutanone. 

Part(d) Step 1: Given information

We need to draw the condensed structural or line-angle formula for the aldehyde or ketone formed when following is oxidized. 

Part(d) Step 2: Explanation

When primary alcohols are oxidized, aldehydes and carboxylic acids are generated; when secondary alcohols are oxidized, ketones are formed. Tertiary alcohols, on the other hand, can't be oxidized without destroying the molecule's C–C bonds.

Given, ${\mathrm{CH}}_3-\mathrm{CH}\left({\mathrm{CH}}_3\right)-{\mathrm{CH}}_2-\mathrm{CH}\left(\mathrm{OH}\right)-{\mathrm{CH}}_3(4-\mathrm{Methylpentane}-2-\mathrm{ol})$ is a secondary alcohol. Hence, it is oxidized to ${\mathrm{CH}}_3-\mathrm{CH}\left({\mathrm{CH}}_3\right)-{\mathrm{CH}}_2-\mathrm{CO}-{\mathrm{CH}}_3(4-\mathrm{Methylpentane}-2-\mathrm{one})$.