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Medical College Admission Test
Chemical and Physical Foundations of Biological Systems

Addition Reaction of Trans-2-Pentene with HBr

Very Hard Organic Chemistry Addition Reactions

A certain alkene, 2-pentene, undergoes an addition reaction with hydrogen bromide to yield a product. Given that 2-pentene can exist in both cis and trans forms, consider the following products formed from each stereoisomer when treated with hydrogen bromide in an electrophilic addition mechanism.

Identify the structure of the major product formed from the reaction of trans-2-pentene with hydrogen bromide, taking into account Markovnikov's rule and potential carbocation rearrangements.

Hint

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