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Chapter 24: Problem 23

Predict products when \(\mathrm{HBr}\) is added to (a) 1 -butene and (b) 2 -butene.

Short Answer

Expert verified
When \(\mathrm{HBr}\) is added to 1-butene, 2-bromobutane is formed. When \(\mathrm{HBr}\) is added to 2-butene, a mixture of 2-bromobutane and 1-bromobutane is formed.

Step by step solution

01

Electrophilic addition to 1-butene

The double bond in 1-butene allows for the electrophilic addition of HBr. The H from the HBr forms a sigma bond with the carbon atom on the end, forming a secondary carbocation intermediate. The bromine atom, being negatively charged, bonds to the secondary carbon, forming 2-bromobutane.
02

Electrophilic addition to 2-butene

In the case of 2-butene, the double bond again allows the HBr molecule to add. The H from the HBr forms a sigma bond with one of the carbon atoms forming a secondary carbocation intermediate. The bromine atom then bonds to the other carbon atom. As the 2-butene molecule can have both cis and trans forms, it leads to two products - 2-bromobutane and 1-bromobutane.

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Most popular questions from this chapter

Identify the functional groups in each of the following molecules: (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\) (b) \(\mathrm{CH}_{3} \mathrm{COOC}_{2} \mathrm{H}_{5}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\)

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