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What are the starting materials to get 2...

What are the starting materials to get 2-methylpropene as the major product?

A

Sodium methoxide and sec-butyl bromide

B

Sodium ethoxide and sec-butyl bromide

C

Sodium tert-butoxide and ethyl bromide

D

Sodium methoxide and tert-butyl bromide

Text Solution

Verified by Experts

The correct Answer is:
D
Alkoxide ions are both powerful nucleophiles and bases. Thus, when they are treated with a tert alkyl halide, they bring its dehydrohalogenation resulting in the formation of alkene. Hence, the alkyl halide taken must be tertiary.
`underset("tert-butyl bromide")(H_(3)C-underset(Br)underset(|)overset(CH_(3))overset(|)(C)-CH_(3))+underset("sodium methoxide")(CH_(3)ONa)undersetunderset(-CH_(3)OH)(-NaBr)rarrunderset("2-methylpropene")(Coverset(3)H_(3)-overset(CH_(3))overset(2|)(C)=Coverset(1)H_(2))`
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