Textbook Question
When tert-butyl bromide is heated with an equal amount of ethanol in an inert solvent, one of the products is ethyl tert-butyl ether.
a. What happens to the reaction rate if the concentration of ethanol is doubled?
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7. Substitution Reactions
Substitution Comparison
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Predict the product of the reaction
A
B
C
D
Verified step by step guidance1
Identify the type of reaction: The reaction involves a secondary alkyl chloride and a potassium acetate (CH3CO2-K+), suggesting a nucleophilic substitution reaction.
Determine the mechanism: Given the secondary carbon and the presence of a good leaving group (Cl), the reaction is likely to proceed via an SN2 mechanism, where the nucleophile attacks the electrophilic carbon, displacing the leaving group.
Analyze the stereochemistry: In an SN2 reaction, the nucleophile attacks from the opposite side of the leaving group, leading to an inversion of configuration at the chiral center.
Predict the product: The acetate ion (CH3CO2-) will attack the carbon bearing the chlorine, replacing the Cl with an OAc group, resulting in an inversion of stereochemistry.
Consider the possible products: The product will be an ester with the acetate group attached to the carbon that originally held the chlorine, and the stereochemistry will be inverted compared to the starting material.
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