Question

Toluene on reaction with the reagent X gave Y, which dissolves in NaHCO\( _3 \) and when reacted with Br\( _2 \)/Fe gave Z. What are X and Z?

• A.

  

• B.

  

• C.

  

• D.

  

Hint:

KMnO\( _4 \)/OH\( ^- \), \(\Delta\) followed by H\( _3 \)O\( ^+ \) is a strong oxidizing agent that converts alkylbenzenes to benzoic acids.

Answer 1

The Correct Option is D

Toluene reacts with KMnO\( _4 \)/OH\( ^- \), \(\Delta\) followed by H\( _3 \)O\( ^+ \) to give benzoic acid (Y). Benzoic acid dissolves in NaHCO\( _3 \) due to the formation of sodium benzoate. When benzoic acid reacts with Br\( _2 \)/Fe, it undergoes electrophilic substitution. The -COOH group is a deactivating and meta-directing group. So, the bromine atom will be substituted at the meta position. Thus, X is KMnO\( _4 \)/OH\( ^- \), \(\Delta\) followed by H\( _3 \)O\( ^+ \) and Z is m-bromobenzoic acid.