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Chapter 23: Q36. (page 924)

Question:What is the major enolate (or carbanion) formed when each compound is treated with LDA?

Short Answer

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Answer

The major enolate (or carbanion) formed when each compound is treated with LDA is shown below:-

Step by step solution

01

LDA (Lithium Diisopropyl Amide)

LDA is a non-nucleophilic strong base that abstracts the protons from the least hindered side.Nitrogen is attached with two bulky isopropyl groups, and due to this, it abstracts protons from the less crowded site.

02

 Step 2: The least hindered site in the given molecules

The least hindered sites in each molecule are shown below:

03

The product formed in the given reactions

Considering the key steps, the major enolate (or carbanion) formed when each compound is treated with LDA is shown below:-

Reaction a

Reaction b

Reaction c

Reaction d

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Most popular questions from this chapter

Question: Nabumetone is a pain reliever and anti-inflammatory agent sold under the brand name of Relafen.

a. Write out a synthesis of nabumetone from ethyl acetoacetate.

b. What ketone and alkyl halide are needed to synthesize nabumetone by direct enolate alkylation?

Question: Rank the labeled protons in each compound in order of increasing acidity.

Question: Both pentane-2,4-dione and ethyl acetoacetate have two carbonyl groups separated by a single carbon atom. Although an equilibrium mixture of pentane-2,4-dione tautomers contains 76% of the enol forms, an equilibrium mixture of ethyl acetoacetate tautomers contains only 8% of the enol forms. Suggest a reason for this difference.

Question: (a) Identify intermediates A–C in the following stepwise conversion of p-isobutyl benzaldehyde to the analgesic ibuprofen.

(b) Direct alkylation of D by treatment with one equivalent of LDA and CH3I does not form ibuprofen. Identify the product of this reaction and explain how it is formed.

Question:What alkyl halides are needed to prepare each ketone using the acetoacetic ester synthesis?
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