Draw the major product of this reaction. Ignore inorganic byproducts. O 1. LDA, -78 °C 2. PhCH₂Br (1 equiv)

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter8: Haloalkanes, Halogenation, And Radical Reactions
Section: Chapter Questions
Problem 8.28P
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**Question 7 of 22**

**Instruction:** Draw the major product of this reaction. Ignore inorganic byproducts.

**Structure:** The depicted structure is a cyclohexanone molecule with a methyl group attached to the ring, adjacent to the carbonyl group.

**Reaction Conditions:**

1. **Reagent 1:** LDA (Lithium diisopropylamide), at -78°C
2. **Reagent 2:** PhCH₂Br (benzyl bromide), 1 equivalent

**Process Explanation:**

- **Step 1:** The use of LDA, a strong, non-nucleophilic base at -78°C, indicates a deprotonation of the most acidic hydrogen, leading to an enolate formation.
  
- **Step 2:** The enolate then acts as a nucleophile, attacking the electrophilic benzyl bromide (PhCH₂Br) to form a new carbon-carbon bond, resulting in the alkylation of the cyclohexanone.

**Expected Major Product:** The major product will feature an additional benzyl group attached via the newly formed carbon-carbon bond, resulting in a benzyl alkylated cyclohexanone.
Transcribed Image Text:**Question 7 of 22** **Instruction:** Draw the major product of this reaction. Ignore inorganic byproducts. **Structure:** The depicted structure is a cyclohexanone molecule with a methyl group attached to the ring, adjacent to the carbonyl group. **Reaction Conditions:** 1. **Reagent 1:** LDA (Lithium diisopropylamide), at -78°C 2. **Reagent 2:** PhCH₂Br (benzyl bromide), 1 equivalent **Process Explanation:** - **Step 1:** The use of LDA, a strong, non-nucleophilic base at -78°C, indicates a deprotonation of the most acidic hydrogen, leading to an enolate formation. - **Step 2:** The enolate then acts as a nucleophile, attacking the electrophilic benzyl bromide (PhCH₂Br) to form a new carbon-carbon bond, resulting in the alkylation of the cyclohexanone. **Expected Major Product:** The major product will feature an additional benzyl group attached via the newly formed carbon-carbon bond, resulting in a benzyl alkylated cyclohexanone.
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