Subjection of 1-bromo-1-methylcyclopentane to the hydrolytic conditions shown leads to a mixture of products. Br -CH3 H₂O heat -CH3 OH -CH3 y =CH₂ + H₂O* + Br A B с a. Which alkene do you expect to be most abundant in the product mixture? b. Provide a stepwise mechanism to explain how the alkene labeled C is formed. c. The reaction above is shown with hydronium ion (pK₂~-1.7) and bromide as products rather than HBr (pKa ~-9). Use acid-base concepts to explain why HBr does not exist when there is an abundance of water.

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5.
Subjection of 1-bromo-1-methylcyclopentane to the hydrolytic conditions shown leads to
a mixture of products.
Br
-CH3
H₂O
heat
-CH3
OH
-CH3
=CH₂ + H3O+ + Br
A
B
с
a. Which alkene do you expect to be most abundant in the product mixture?
b. Provide a stepwise mechanism to explain how the alkene labeled C is formed.
c. The reaction above is shown with hydronium ion (pK₂~-1.7) and bromide as products
rather than HBr (pKa ~ -9). Use acid-base concepts to explain why HBr does not exist
when there is an abundance of water.
Transcribed Image Text:5. Subjection of 1-bromo-1-methylcyclopentane to the hydrolytic conditions shown leads to a mixture of products. Br -CH3 H₂O heat -CH3 OH -CH3 =CH₂ + H3O+ + Br A B с a. Which alkene do you expect to be most abundant in the product mixture? b. Provide a stepwise mechanism to explain how the alkene labeled C is formed. c. The reaction above is shown with hydronium ion (pK₂~-1.7) and bromide as products rather than HBr (pKa ~ -9). Use acid-base concepts to explain why HBr does not exist when there is an abundance of water.
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