Organic Compounds Containing Halogens Question 92

Question: Reaction of t-butyl bromide with sodium methoxide produces

[CBSE PMT 1994]

Options:

A) Isobutane

B) Isobutylene

C) Sodium t-butoxide

D) t-butyl methyl ether

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Answer:

Correct Answer: B

Solution:

$ CH_3-\underset{CH_3}{\overset{CH_3}{\mathop{\underset{|}{\overset{|}{\mathop{C-}}}}}}Br+CH_3ONa\xrightarrow{Elimination} $

$ \underset{Isobutylene}{\mathop{CH_3-\overset{CH_3}{\mathop{\overset{|}{\mathop{C=}}}}CH_2}}+CH_3OH+NaBr $

$ CH_3ONa\to CH_3{O^{-}}+N{a^{+}} $ methoxide ion $ (CH_3{O^{-}}) $ is a strong base, therefore it abstract proton from $ 3^{o} $ alkyl halide and favours elimination reaction.