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Halogenation of Alpha Carbon

A compound A ...

Question

A compound A has a molecular formula $C_{2} C l_{3} O H$ . It reduces Fehling's solution and on oxidation, gives a monocarboxylic acid B. A can be obtained by the action of chlorine on ethyl alcohol. A is :

A

chloroform

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B

chloral

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C

methyl chloride

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D

monochloroacetic acid

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Solution

The correct option is B chloral
The compound reduces Fehling's solution, so it must contain aldehyde group,-CHO. again oxidation gives monocarboxylic acid (-COOH) which suggest containing -CHO group. A can be prepared from ethyl alcohol by chlorination as follows
$C H_{3} C H_{2} O H + C l_{2} \to C H_{3} C H O$
$C H_{3} C H O + C l_{2} \to C C l_{3} C H O$ (chloral).
So, option B is the right answer.

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