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CUET · CHEMISTRY · PYQ PAPER 2023

Answer the question on basis of passage given below :
A ketone \([A]\) which undergoes haloform reaction gives compound \([B]\) on reduction. Compound
\([B]\) on heating with sulphuric acid gives compound \([C]\) which forms monozonide \([D]\). The compound [D] on hydrolysis in the presence of zinc dust gives compound [E]. 
Compound [E] on oxidation gives \(C _2 H _4 O _2\) [F]
The compound \([ B ]\) formed can be prepared from reaction of aq. KOH . with :

  1. A \(CH _3 CH _2 CH _2- Cl\)
  2. B \(CH _3- CH ( Cl )- CH _3\)
  3. C \(CH _3- CH ( Cl )- CH _2- CH _3\)
  4. D \(\left( CH _3\right)_3 C - Cl\)
Verified Solution

Answer & Solution

Correct Answer

(C) \(CH _3- CH ( Cl )- CH _2- CH _3\)

Step-by-step Solution

Detailed explanation

Oxidation of [E] gives \(C_2H_4O_2\) [F] (Acetic acid). Thus, [E] is \(CH_3CHO\) (Acetaldehyde). Ozonolysis of [C] followed by hydrolysis gives [E]. If [E] is \(CH_3CHO\), then [C] must be \(CH_3CH=CHCH_3\) (2-butene). Dehydration of [B] gives [C]. So, [B] is…
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