Question

t-butyl chloride preferably undergo hydrolysis by

• A. \( \text{S}_\text{N}1 \) mechanism
• B. \( \text{S}_\text{N}2 \) mechanism
• C. any of (a) and (b)
• D. None of the above

Hint:

In \( \text{S}_\text{N}1 \) reactions, the stability of the carbocation intermediate plays a crucial role. Tertiary alkyl halides, like t-butyl chloride, favor \( \text{S}_\text{N}1 \) reactions due to the stability of the carbocation.

Answer 1

The Correct Option is A

The correct answer is the \( \text{S}_\text{N}1 \) mechanism. This preference is because of the following reasons:

1. Stability of Carbocation: The t-butyl group (\((CH_3)_3C-\)) forms a tertiary carbocation upon loss of the chloride ion. Tertiary carbocations are more stable compared to primary or secondary ones due to hyperconjugation and the inductive effect from the surrounding methyl groups.
2. Reaction Mechanism: In the \( \text{S}_\text{N}1 \) mechanism, the reaction proceeds via a two-step process: first forming a carbocation intermediate, which is stabilized in the case of t-butyl chloride, followed by a nucleophile attacking the planar carbocation.
3. Steric Hindrance: The bulky t-butyl group creates steric hindrance, which disfavors a bimolecular \( \text{S}_\text{N}2 \) reaction where the nucleophile would attack directly.

In conclusion, the stability of the carbocation and steric effects make the \( \text{S}_\text{N}1 \) pathway favorable for t-butyl chloride hydrolysis.

Answer 2

t-Butyl chloride undergoes hydrolysis by the \( \text{S}_\text{N}1 \) mechanism. This is because t-butyl chloride is a tertiary alkyl halide, which stabilizes the formation of a carbocation intermediate.
The \( \text{S}_\text{N}1 \) mechanism involves the formation of a carbocation intermediate, followed by the nucleophilic attack by water to form the alcohol. 
The reaction proceeds via a two-step mechanism: the first step is the leaving of the halide ion to form a carbocation, followed by the attack of water.
The \( \text{S}_\text{N}2 \) mechanism is less favorable for t-butyl chloride because the steric hindrance from the bulky t-butyl group makes it difficult for the nucleophile to attack the carbon directly. 
Thus, the correct answer is \( \text{S}_\text{N}1 \) mechanism.