/*! This file is auto-generated */ .wp-block-button__link{color:#fff;background-color:#32373c;border-radius:9999px;box-shadow:none;text-decoration:none;padding:calc(.667em + 2px) calc(1.333em + 2px);font-size:1.125em}.wp-block-file__button{background:#32373c;color:#fff;text-decoration:none} Q57. Question: Draw a stepwise mechan... [FREE SOLUTION] | 91影视

91影视

Log out

Learning Materials

Features

Discover

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

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Over 30 million students worldwide already upgrade their learning with 91影视!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

Question: As we learned in Chapter 20, organolithium reagents (RLi) are strong bases that readily react with acidic protons. Why aren鈥檛 organolithium reagents used to generate enolates?

Question: The last step in the synthesis of 尾-vetivone (Problem 23.61) involves treatment of C with CH3Li to form an intermediate X, which forms 尾-vetivone with aqueous acid. Identify the structure of X and draw a mechanism for converting X to 尾-vetivone.

Question: Draw the product formed when each starting material is treated with LDA in THF solution at 鈥�780C.

Question: Which carbonyl compound in each pair exhibits the higher percentage of the enol tautomer?

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

Recommended explanations on Chemistry Textbooks

Organic Chemistry

Read Explanation

Making Measurements

Read Explanation

The Earths Atmosphere

Read Explanation

Inorganic Chemistry

Read Explanation

Chemistry Branches

Read Explanation

Nuclear Chemistry

Read Explanation
View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.