Practicing Success

Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Haloalkanes and Haloarenes

Question:

Statement I: Hydrolysis of (–)-2-Bromooctane proceeds with inversion of configuration

Statement II: This reaction proceeds through the formation of a carbocation

Options:

Both statement I and statement II are correct and statement II is the correct explanation of statement I

Both statement I and statement II are correct but statement II is not the correct explanation of statement I

Statement I is correct but statement II is false

Statement I is false but statement II is correct

Correct Answer:

Statement I is correct but statement II is false

Explanation:

The correct answer is (3) Statement I is correct but statement II is false.

Statement I: Hydrolysis of (–)-2-Bromooctane proceeds with inversion of configuration

This statement is true. The hydrolysis of 2-bromooctane proceeds through the SN2 mechanism, which is a nucleophilic substitution reaction that proceeds with inversion of configuration.

Statement II: This reaction proceeds through the formation of a carbocation

The statement is false. The SN2 reaction does not form a carbocation intermediate. Instead, it proceeds through a transition state in which the nucleophile and leaving group are both attached to the carbon atom. The transition state is very unstable, and it quickly collapses to form the product.

The SN2 reaction is a concerted reaction, which means that the nucleophile attacks the carbon atom and the leaving group leaves at the same time. This is why the SN2 reaction does not form a carbocation intermediate. If the leaving group left first, then there would be a carbocation intermediate. However, the nucleophile attacks the carbon atom so quickly that there is no time for a carbocation to form.

The SN2 reaction is a very fast reaction, and it is often used to synthesize compounds with inverted stereochemistry. This is because the nucleophile attacks the carbon atom from the opposite side of the leaving group. This results in the nucleophile replacing the leaving group on the opposite side of the carbon atom, which is the opposite side of where it started.