Textbook Question
SN1 substitution and E1 elimination frequently compete in the same reaction.
a. Propose a mechanism and predict the products for the solvolysis of 2-bromo-2,3,3-trimethylbutane in methanol.
8. Elimination Reactions
Cumulative Substitution/Elimination
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Predict the mechanism for the following reactions. Provide the full mechanism and draw the final product.
A
B
C
D
Verified step by step guidance1
Identify the type of reaction: The reaction involves a cyclohexane ring with a bromine (Br) and a hydroxyl (OH) group. The reagent is NaSH, which suggests a nucleophilic substitution reaction.
Determine the leaving group: In this reaction, the bromine (Br) is the leaving group. It is a good leaving group due to its ability to stabilize the negative charge after leaving.
Identify the nucleophile: The nucleophile in this reaction is the SH- ion from NaSH. It will attack the carbon atom bonded to the bromine.
Predict the mechanism: The reaction likely follows an SN2 mechanism, where the SH- ion attacks the carbon from the opposite side of the leaving group, leading to an inversion of configuration at that carbon center.
Draw the final product: After the nucleophilic attack and the departure of the bromine, the final product will have the SH group replacing the Br, with the OH group remaining in its original position.
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