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Chapter 23: Q57. (page 924)

Question: Draw a stepwise mechanism showing how two alkylation products are formed in the following reaction.

Short Answer

Expert verified

Answer

Stepwise mechanism:

Step 1

Step 2

Step by step solution

01

Enolate ion formation using LDA

Strong organic bases such as LDA can be used to drive the ketone-enolate equilibrium completely to the enolate side.

The bulky isopropyl groups make LDA non-nucleophilic and useful for deprotonation.

02

Alkylation product mechanism

The mechanism for alkylation products is given as:

In the first step, the acidic hydrogen is deprotonated by diisopropyl amide giving a resonance stabilized enolate ion.

Formation of resonance stabilized enolate

In the next step, the enolate reacts with methyl bromide, attacking the methyl group and expelling the bromide ion, and forming the alkylated product

Reaction with alkyl halide

Formation of alkylated product

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Most popular questions from this chapter

Question: What enolate is formed when each ketone is treated with LDA in THF solution? What enolate is formed when these same ketones are treated with NaOCH3in CH3OHsolution?

Question: What hydrogen atoms in each compound have a pka≤ 25?

Question:What ketones are prepared by the following reactions?

Question: What reaction conditions—base, solvent, and temperature—are needed to convert ketone A to either B or C by an intramolecular alkylation reaction?

Question: As we learned in Chapter 20, organolithium reagents (RLi) are strong bases that readily react with acidic protons. Why aren’t organolithium reagents used to generate enolates?
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