Identify the set of reagents/reaction conditions X and Y in the following set of transformations: CH_3CH_2CH_2Br X Product Y (CH_3)_2CHBr

JEE Main Chemistry question

Identify the set of reagents/reaction conditions and in the following set of transformations:

CH_3CH_2CH_2Br Product

(A) dilute aq. NaOH, ; HBr/acetic acid,
(B) conc., alc. NaOH, ; HBr/acetic acid, Correct
(C) dilute aq. NaOH, ; ,
(D) conc., alc. NaOH, ; ,

Answer: (B)

Solution

Concentrated alcoholic NaOH under heating (80°C) promotes E2 dehydrohalogenation of 1-bromopropane to propene (not substitution, which dilute aqueous NaOH would favour). Treating propene with HBr in acetic acid then adds HBr across the double bond following Markownikoff's

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Question ID VK-148284