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Question 59 of 72

Q.n-propyl bromide on reaction with alcoholic KOH gives:

(a) Butyl alcohol
(b) Propene
(c) Butene
(d) Propyl alcohol
Puducherry TnboardTamil Nadu HSC First Year (DGE) Board 2020MCQ· 1mImportance★★★★★
82% · 59/72 Questions
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Alcoholic KOH favours elimination over substitution, so n-propyl bromide (CH3-CH2-CH2-Br) loses HBr to form propene (CH3-CH=CH2).

Whether a haloalkane undergoes substitution or elimination with KOH depends on the solvent. Aqueous KOH provides OH- ions, which are good nucleophiles and favour substitution (SN2), giving an alcohol. Alcoholic KOH, however, generates ethoxide ions (from the solvent) which are strong, bulky bases that preferentially abstract a beta-hydrogen atom from the substrate, in an E2 elimination, expelling the bromide ion and forming a carbon-carbon double bond.

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