Q.

A halogen compound ‘A’ on hydrolysis with dilute alkali followed by acidification gives acetic acid. The compound x is

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a

ClCH2CH2Cl

b

CH3CHCl2

c

ClCH2CHCl2

d

CH3CCl3

answer is D.

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Detailed Solution

Hydrolysis: When a halogen compound is hydrolyzed with dilute alkali (NaOH), halogens (Cl) are replaced with hydroxyl groups (OH). Multiple hydroxyl groups may form, leading to an unstable intermediate.

Acidification: After hydrolysis, acidification converts the unstable intermediate into the stable carboxylic acid form, which in this case is acetic acid (CH3COOH).

Identifying the compound: To produce acetic acid, the halogen compound must have the potential to yield a molecule with 2 carbon atoms and eventually form the CH3COOH group.

Analyzing the Options:

Option (a): ClCH2CH2Cl

On hydrolysis, it forms HOCH2CH2OH (ethylene glycol). This does not yield acetic acid after acidification.

Option (b): CH3CHCl2

On hydrolysis, it forms CH3C(OH)2H (geminal diol). Acidification stabilizes the diol by losing water to form CH3CHO (acetaldehyde), not acetic acid.

Option (c): ClCH2CHCl2

On hydrolysis, it forms HOCH2C(OH)2H. Acidification stabilizes this compound to form formic acid (HCOOH), not acetic acid.

Option (d): CH3CCl3

On hydrolysis, it forms CH3C(OH)3 (geminal triol). Acidification stabilizes this intermediate by converting it to acetic acid (CH3COOH).

The correct halogen compound ‘A’ is CH3CCl3 (Option d).

Hydrolysis of CH3CCl3 replaces the chlorine atoms with hydroxyl groups. Acidification stabilizes the intermediate to form acetic acid. None of the other options can yield acetic acid under these conditions.

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