Practicing Success

Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Haloalkanes and Haloarenes

Question:

In SN2 reaction, the correct order of reactivity for the following compounds:

CH3Cl,CH3CH2Cl, (CH3)2CHCl and (CH3)3CCl is

Options:

CH3Cl > CH3CH2Cl > (CH3)2CHCl > (CH3)3CCl

CH3CH2Cl > CH3Cl > (CH3)2CHCl > (CH3)3CCl

(CH3)2 CHCl > CH3CH2Cl > CH3Cl > (CH3)3CCl

CH3Cl > (CH3)2CHCl > CH3CH2Cl > (CH3)3CCl

Correct Answer:

CH3Cl > CH3CH2Cl > (CH3)2CHCl > (CH3)3CCl

Explanation:

The correct answer is option 1. CH3Cl > CH3CH2Cl > (CH3)2CHCl > (CH3)3CCl.

Reactivity order 1° halide > 2° halide > 3° halide.

Reactivity of SN2 = \(\frac{1}{\text{steric hindrance}}\).

Here is a detailed explanation for the correct order of reactivity in an SN2 reaction for the given compounds:

1. CH3Cl (methyl chloride): This compound contains a primary carbon atom bonded to the chlorine. Primary carbon atoms have the least steric hindrance because they are only bonded to one alkyl group. The absence of additional alkyl groups allows the nucleophile to approach the carbon atom more easily, resulting in higher reactivity. Therefore, CH3Cl is the most reactive compound among the given options.

2. CH3CH2Cl (ethyl chloride): This compound has a secondary carbon atom bonded to the chlorine. Secondary carbon atoms have more steric hindrance compared to primary carbon atoms due to the presence of an additional alkyl group. The presence of the ethyl group introduces some hindrance, making the approach of the nucleophile slightly more difficult. As a result, CH3CH2Cl is less reactive than CH3Cl but more reactive than compounds with higher steric hindrance.

3. (CH3)2CHCl (isopropyl chloride): This compound contains a secondary carbon atom bonded to the chlorine, similar to ethyl chloride. However, (CH3)2CHCl has two methyl groups attached to the secondary carbon, resulting in increased steric hindrance compared to ethyl chloride. The presence of two alkyl groups makes the approach of the nucleophile even more difficult, leading to decreased reactivity compared to both CH3Cl and CH3CH2Cl.

4. (CH3)3CCl (tert-butyl chloride): This compound has a tertiary carbon atom bonded to the chlorine. Tertiary carbon atoms have the highest steric hindrance because they are bonded to three alkyl groups. The bulky nature of the three methyl groups significantly obstructs the approach of the nucleophile, resulting in the lowest reactivity among the given options.

Therefore, the correct order of reactivity for the compounds in an SN2 reaction is:

CH3Cl > CH3CH2Cl > (CH3)2CHCl > (CH3)3CCl