Question

Draw the structure of the major product of each step in the following three-step synthesis. Show the formal charges, where applicable. As a start, the benzene ring is drawn for you in each product.

Answer 1

Concepts and reason

Oxidation of alkyl benzene:

Alkyl benzene is an organic compound in which the benzylic carbon is oxidized to benzoic acid in the presence of.

Nitration:

Nitronium ion, () is an electrophile which reacts with benzene to form nitro-benzene. It is an example of an electrophilic substitution reaction.

Bromination:

Bromine acts as an electrophile in the electrophilic substitution reaction. It reacts with the pi electrons of benzene C=C (nucleophile) in the presence of to give bromo-benzene. It is also an example of an electrophilic substitution reaction.

Fundamentals

The mechanism for the nitration of benzene:

Step 1: Generation of nitronium ion, :

Step 2: Formation of an arenium ion:

Step 3: Deprotonation of an arenium ion:

The mechanism for the bromination of benzene:

Step 1: Formation of an electrophile, :

Step 2: Formation of an arenium ion:

Step 3: Deprotonation of an arenium ion;

The Side-chain oxidation reaction of cumene:

Ans: