A mechanism for the reaction of bromine with 4,4-dimethylcyclopentene in water is shown below. Which of the following statements about this mechanism is correct? Step 1 Br Br Br + Br Br Step 2 Br OH2 OH2 Br Br OH2 Step 3 + Hо H OH O In Step 1, bromine could add to the other face of the alkene, giving a bromonium ion that is the enantiomer of the one shown. O In Step 2, water could attack the other carbon atom of the bromonium ion, leading to the enantiomer of the product shown. O This mechanism is complete and correct. O In Step 2, water could attack the bromonium ion from the other side, leading to the cis product.

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter10: Organohalides
Section10.SE: Something Extra
Problem 20MP: In light of the fact that tertiary alkyl halides undergo spontaneous dissociation to yield a...
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A mechanism for the reaction of bromine with 4,4-dimethylcyclopentene in water is shown below.
Which of the following statements about this mechanism is correct?
Step 1
Br
Br
Br
+ Br
Br
Step 2
Br
;OH
OH2
Br
Br
XX
..
Step 3
+ Hо
HO:)
H.
O In Step 1, bromine could add to the other face of the alkene, giving a bromonium ion that is the enantiomer of
the one shown.
O In Step 2, water could attack the other carbon atom of the bromonium ion, leading to the enantiomer of the
product shown.
O This mechanism is complete and correct.
O In Step 2, water could attack the bromonium ion from the other side, leading to the cis product.
Transcribed Image Text:A mechanism for the reaction of bromine with 4,4-dimethylcyclopentene in water is shown below. Which of the following statements about this mechanism is correct? Step 1 Br Br Br + Br Br Step 2 Br ;OH OH2 Br Br XX .. Step 3 + Hо HO:) H. O In Step 1, bromine could add to the other face of the alkene, giving a bromonium ion that is the enantiomer of the one shown. O In Step 2, water could attack the other carbon atom of the bromonium ion, leading to the enantiomer of the product shown. O This mechanism is complete and correct. O In Step 2, water could attack the bromonium ion from the other side, leading to the cis product.
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