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Question 21.6: Alkene Addition Reactions Determine the products of each rea...

Alkene Addition Reactions

Determine the products of each reaction.

(a) CH_3CH_2CH = CH_2+ Br_2 \longrightarrow      (b) CH_3CH_2CH = CH_2+ HBr \longrightarrow

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(a) The reaction of 1-butene with bromine is an example of a symmetric addition. The bromine adds across the double bond, and each carbon forms a single bond to a bromine atom. H-\overset{\overset{H}{|} }{\underset{\overset{|}{H} }{C}}- \overset{\overset{H}{|} }{\underset{\overset{|}{H} }{C}}-\overset{\overset{H}{|} }{C} = \overset{\overset{H}{|} }{C}- H + Br  –  Br\longrightarrow H -\overset{\overset{H}{|} }{\underset{\overset{|}{H} }{C}} -\overset{\overset{H}{|} }{\underset{\overset{|}{H} }{C}}-\overset{\overset{H}{|} }{\underset{\overset{|}{Br} }{C}}-\overset{\overset{Br}{|} }{\underset{\overset{|}{H} }{C}} – H
(b) The reaction of 1-butene with hydrogen bromide is an example of an unsymmetrical addition. Apply Markovnikov’s rule to determine which carbon the hydrogen bonds with and which carbon the bromine atom bonds with. Markovnikov’s rule predicts that the hydrogen bonds to the end carbon in this case. H-\overset{\overset{H}{|} }{\underset{\overset{|}{H} }{C}}- \overset{\overset{H}{|} }{\underset{\overset{|}{H} }{C}}-\overset{\overset{H}{|} }{C} = \overset{\overset{H}{|} }{C}- H + H  –  Br\longrightarrow H -\overset{\overset{H}{|} }{\underset{\overset{|}{H} }{C}} -\overset{\overset{H}{|} }{\underset{\overset{|}{H} }{C}}-\overset{\overset{H}{|} }{\underset{\overset{|}{Br} }{C}}-\overset{\overset{H}{|} }{\underset{\overset{|}{H} }{C}} – H

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