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Question: A compound A has a molecular formula \(C_{2}Cl_{3}OH.\) It reduces Fehling solution and on oxidation...

A compound A has a molecular formula C2Cl3OH.C_{2}Cl_{3}OH. It reduces Fehling solution and on oxidation gives a monocarboxylic acid (2). A is obtained by action of chlorine on ethyl alcohol. A is.

A

Chloral

B

CHCl3CHCl_{3}

C

CH3ClCH_{3}Cl

D

Chloroacetic acid

Answer

Chloral

Explanation

Solution

C2Cl3OHA+Fehlingsol.Cu2ORed6muppt\underset{A}{C_{2}Cl_{3}OH} + \text{Fehlingsol.} \rightarrow \underset{\text{Red}\mspace{6mu}\text{ppt}}{Cu_{2}O}

It means –CHO group is present.

C2Cl3OHAOxidationCCl3COOHMonocarboxylicacid\underset{A}{C_{2}Cl_{3}OH}\overset{\quad\text{Oxidation}\quad}{\rightarrow}\underset{\text{Monocarboxylicacid}}{CCl_{3} - COOH}

It means only one –CHO group is present.

C2H5OH+Cl2CH3CHO+2HClC_{2}H_{5}OH + Cl_{2} \rightarrow CH_{3}CHO + 2HCl

CH3CHO+3Cl2CCl3CHOChloral+3HClCH_{3}CHO + 3Cl_{2} \rightarrow \underset{\text{Chloral}}{CCl_{3}CHO} + 3HCl