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CUET · CHEMISTRY · PYQ PAPER 2023

"An alkyl halide with molecular formula \(C6H13Br\) on dehydrohalogenation gave two isomeric alkenes \(A\) and \(B\) with molecular formula \(C6H12\). On reductive ozonolysis, \(A\) and \(B\) gave four compounds \(CH3COCH3\), \(CH3CHO\), \(CH3CH2CHO\) and \((CH3)2CHCHO\). The alkyl halide is :"

  1. A 2-Bromohexane
  2. B 2,2-Dimethyl-1-bromobutane
  3. C 2-Bromo-2,3-dimethylbutane
  4. D 3-Bromo-2-methylpentane
Verified Solution

Answer & Solution

Correct Answer

(D) 3-Bromo-2-methylpentane

Step-by-step Solution

Detailed explanation

Ozonolysis products: \(CH_3COCH_3\), \(CH_3CHO\), \(CH_3CH_2CHO\), \((CH_3)_2CHCHO\). Reconstruct alkenes A and B: \(CH_3COCH_3 + CH_3CH_2CHO \rightarrow CH_3-C(CH_3)=CH-CH_2CH_3\) (2-methylpent-2-ene). \(CH_3CHO + (CH_3)_2CHCHO \rightarrow CH_3-CH=CH-CH(CH_3)_2\)…
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