The hydrolysis reaction (with aq. NaOH) that takes place at the slowest rate, among the following, is :
Answer: (A) (A) chloro-dimethylbenzene (aryl chloride) phenol derivative. In an aryl chloride the bond has partial double-bond character due to resonance of the halogen lone pair into the ring, and the carbon is hybridised, holding the halogen tightly.
- A.(A) chloro-dimethylbenzene (aryl chloride) phenol derivative✓
- B.(B) (ethyl chloride)
- C.(C) (allyl chloride)
- D.(D) (benzyl chloride)
Correct Answer
(A) (A) chloro-dimethylbenzene (aryl chloride) phenol derivative
Solution & Explanation
In an aryl chloride the bond has partial double-bond character due to resonance of the halogen lone pair into the ring, and the carbon is hybridised, holding the halogen tightly. Nucleophilic substitution/hydrolysis therefore requires drastic conditions and is the slowest. Ethyl chloride (, ), allyl chloride and benzyl chloride (both give resonance-stabilised carbocations / fast ) all hydrolyse readily, so the aryl chloride reacts slowest.
