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Question
Reaction of 2,3-dimethyl-1-butene with HBr leads to an alkyl bromide, . On treatment of this alkyl bromide with KOH in methanol, elimination of HBr occurs and a hydrocarbon that is isomeric with the starting alkene is formed. What is the structure of this hydrocarbon, and how do you think it is formed from the alkyl bromide?
Step-by-Step Solution
VerifiedThe structure of hydrocarbon formed from alkyl bromide is,
When hydrogen halide reacts with alkenes, it forms alkyl halides. The addition of hydrogen bromide in alkene forms alkyl bromide. The addition is Markovnikov, where hydrogen attached to that carbon has more hydrogen atoms.
When 2,3-Dimethyl-1-butene is treated with HBr, it forms 2-Bromo-2,3-dimethylbutane. The further reaction of 2-bromo-2,3-dimethylbutane with KOH in methanol results in the formation of 2,3-Dimethyl-2-butene by eliminating HBr. The double bond formed is highly substituted.
Formation of hydrocarbon formed from the alkyl bromide