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 :"
- A 2-Bromohexane
- B 2,2-Dimethyl-1-bromobutane
- C 2-Bromo-2,3-dimethylbutane
- D 3-Bromo-2-methylpentane
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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