Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Haloalkanes and Haloarenes

Question:

What will be the configuration of the product formed during the given reaction?

Options:

Retention

Inversion

Racemization

No Product will be formed

Correct Answer:

Retention

Explanation:

The correct answer is option 1. Retention.

 

The reaction in the image shows a chiral alcohol reacting with $SOCl_{2}$ in the presence of ether.

1. Mechanism: $S_{N}i$ (Internal Nucleophilic Substitution)

When $SOCl_{2}$ reacts with an alcohol in a non-polar or weakly polar solvent like ether, it proceeds via the $S_{N}i$ mechanism.

  • Step 1: The alcohol reacts with $SOCl_{2}$ to form an intermediate called an alkyl chlorosulfite.

  • Step 2: This intermediate decomposes. The chlorine atom from the chlorosulfite group attacks the carbon from the same side that the leaving group was attached to.

  • Result: Because the attack happens from the front (the same side), the stereochemistry is preserved.

2. Configuration of the Product

Since the nucleophile ($Cl$) replaces the hydroxyl group ($-OH$) at the exact same position without any backside attack, the configuration of the product is Retention.

  • Statement: The correct answer is Option 1: Retention.