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Question
2,3-dimethyl-2-butene can be prepared by heating which of the following compounds with a strong acid?
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Solution
The correct option is D (CH3)3C−CH=CH2
(CH3)3C−CH=CH2Strongacid−−−−−−→ΔCH3C(CH3)=C(CH3)CH3
In presence of strong acid, rearrangement reaction occurs.
In the first step, a proton is added.
(CH3)3C−CH=CH2Strongacid−−−−−−→Δ(CH3)3C−CH+−CH3
In the next step, a methyl group migrates.
(CH3)3C−CH+−CH3→(CH3)2C+−C(CH3)H−CH3
In the last step, a proton is removed.
(CH3)2C+−C(CH3)H−CH3−H+−−−→CH3C(CH3)=C(CH3)CH3
(CH3)3C−CH=CH2Strongacid−−−−−−→ΔCH3C(CH3)=C(CH3)CH3
In presence of strong acid, rearrangement reaction occurs.
In the first step, a proton is added.
(CH3)3C−CH=CH2Strongacid−−−−−−→Δ(CH3)3C−CH+−CH3
In the next step, a methyl group migrates.
(CH3)3C−CH+−CH3→(CH3)2C+−C(CH3)H−CH3
In the last step, a proton is removed.
(CH3)2C+−C(CH3)H−CH3−H+−−−→CH3C(CH3)=C(CH3)CH3
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