< Question 27 of 85 Submit This proposed reaction would not work. Identify what is wrong with it. 1. LDA, -78 °C 2. benzyl bromide methanol A) The LDA creates an enolate nucleophile to react with the benzyl bromide in a substitution reaction. However, the bromide is not a good enough leaving group for this reaction. Tap here or pull up for additional resources < Question 27 of 85 Submit A) The LDA creates an enolate nucleophile to react with the benzyl bromide in a substitution reaction. However, the bromide is not a good enough leaving group for this reaction. B) The LDA creates an enolate nucleophile to react with the benzyl bromide in a substitution reaction. However, the product of this reaction would have one less CH2 group than the proposed product. C) The LDA reacts rapidly with the alcohol solvent creating an alkoxide base. This base is a thermodynamic base and would remove a proton from the more substituted position resulting in alkylation at the other alpha carbon. D) The LDA creates an enolate nucleophile to react with the benzyl bromide in a substitution reaction. However, the reaction conditions are too cold and would result in alkylation at the other alpha carbon (thermodynamic) rather than the proposed kinetic product. Tap here or pull up for additional resources

Chemistry
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Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Chapter1: Chemical Foundations
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Question 27 of 85
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This proposed reaction would not work. Identify
what is wrong with it.
1. LDA, -78 °C
2. benzyl bromide
methanol
A) The LDA creates an enolate nucleophile to
react with the benzyl bromide in a
substitution reaction. However, the bromide
is not a good enough leaving group for this
reaction.
Tap here or pull up for additional resources
Transcribed Image Text:< Question 27 of 85 Submit This proposed reaction would not work. Identify what is wrong with it. 1. LDA, -78 °C 2. benzyl bromide methanol A) The LDA creates an enolate nucleophile to react with the benzyl bromide in a substitution reaction. However, the bromide is not a good enough leaving group for this reaction. Tap here or pull up for additional resources
<
Question 27 of 85
Submit
A) The LDA creates an enolate nucleophile to
react with the benzyl bromide in a
substitution reaction. However, the bromide
is not a good enough leaving group for this
reaction.
B) The LDA creates an enolate nucleophile to
react with the benzyl bromide in a
substitution reaction. However, the product
of this reaction would have one less CH2
group than the proposed product.
C) The LDA reacts rapidly with the alcohol
solvent creating an alkoxide base. This base
is a thermodynamic base and would remove
a proton from the more substituted position
resulting in alkylation at the other alpha
carbon.
D) The LDA creates an enolate nucleophile to
react with the benzyl bromide in a
substitution reaction. However, the reaction
conditions are too cold and would result in
alkylation at the other alpha carbon
(thermodynamic) rather than the proposed
kinetic product.
Tap here or pull up for additional resources
Transcribed Image Text:< Question 27 of 85 Submit A) The LDA creates an enolate nucleophile to react with the benzyl bromide in a substitution reaction. However, the bromide is not a good enough leaving group for this reaction. B) The LDA creates an enolate nucleophile to react with the benzyl bromide in a substitution reaction. However, the product of this reaction would have one less CH2 group than the proposed product. C) The LDA reacts rapidly with the alcohol solvent creating an alkoxide base. This base is a thermodynamic base and would remove a proton from the more substituted position resulting in alkylation at the other alpha carbon. D) The LDA creates an enolate nucleophile to react with the benzyl bromide in a substitution reaction. However, the reaction conditions are too cold and would result in alkylation at the other alpha carbon (thermodynamic) rather than the proposed kinetic product. Tap here or pull up for additional resources
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