Hydrocarbons 2 Question 3

3. The major product of the following addition reaction is

$$ \mathrm{H}{3} \mathrm{C}-\mathrm{CH}=\mathrm{CH}{2} \xrightarrow{\mathrm{Cl}{2} / \mathrm{H}{2} \mathrm{O}} $$

(a) $\mathrm{CH}{3}-\underset{\mathrm{Cl}}{\mathrm{CH}}-\underset{\mathrm{OH}}{\mathrm{CH}{2}}$

(2019 Main, 12 April I)

(b)

(c)

(d)

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Answer:

Correct Answer: 3. (d)

Solution:

  1. The major product of the given addition reaction is

In this reaction, $\mathrm{H}_{2} \mathrm{O}$ is used as a solvent and the major product of the reaction will be a vicinal halohydrin. A halohydrin is an organic molecule that contains both $\mathrm{OH}$ group and a halogen. In a vicinal halohydrin, the $\mathrm{OH}$ and halogen are bonded to adjacent carbons.

$\mathrm{H}{3} \mathrm{C}-\mathrm{CH}=\mathrm{CH}{2} \xrightarrow{\mathrm{Cl}{2} / \mathrm{H}{2} \mathrm{O}} \mathrm{H}{3} \mathrm{C}-\underset{\mathrm{OH}}{\mathrm{CH}}-\underset{\mathrm{Cl}}{\mathrm{CH}{2}}+$

A chlorohydrin (major product)

(Minor product)

The reaction proceeds through following mechanism :