Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 20: Q81P (page 764)

Draw a stepwise mechanism for the following reaction of a Grignard reagent with a cyclic amide.

Short Answer

Expert verified

Grignard reaction occurs when the alkyl part of the Grignard reagent attacks at the carbonyl carbon. Subsequently, the hydrolysis forms the substituted alcohol.

The excess Grignard reagent substitutes another alkyl group via the bimolecular substitution reaction.

Step by step solution

01

Grignard reaction

Grignard reaction occurs when the alkyl part of the Grignard reagent attacks at the carbonyl carbon. Subsequently, the hydrolysis forms the substituted alcohol.

The excess Grignard reagent substitutes another alkyl group via the bimolecular substitution reaction.

02

Explanation

In the first step, the anion part of the ethyl magnesium bromide attacks at the carbonyl carbon followed by the hydrolysis.

In the second step, the other ethyl magnesium bromide molecule attacks at the alcoholic carbon and eliminates the hydroxide ion.

The mechanism is shown as:

Grignard reaction mechanism

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.

Start your free trial

Over 30 million students worldwide already upgrade their learning with Vaia!

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

Draw the products formed when A or B is treated with each reagent. In some cases,no reaction occurs.

a.NaBH4,CH3OHb.[1]LiAIH4;[2]H2Oc.[1]CH3MgBr;[2]H2Od.[1]C6H5Li;[2]H2Oe.[1]Na2Cr2O7;H2SO4,H2O

Reaction of benzyl magnesium chloride with formaldehyde yields alcohols N and P after protonation. Draw a stepwise mechanism that shows how both products are formed.

stereochemistry of the products of reduction depends on the reagent used,as you learned in Sections 20.5 and 20.6. With this in mind, how would you convert3,3-dimethylbutan-2-one [CH3COCCH3] to: (a) racemic 3,3-dimethylbutan-2-ol [CH3CHOHCCH33];(b) only (R)-3,3-dimethylbutan-2-ol; (c) only (S)-3,3-dimethylbutan-2-ol?

Draw all stereoisomers formed in each reaction.

Draw the product formed when the α,β-unsaturated ketone A is treated with each reagent.

(a)NaBH4,CH3OH(b)H2,(1equiv),Pd-C(c)H2,(excess),Pd-C(d)[1]CH3Li;[2]H2O(e)[1]CH3CH2MgBr;[2]H2O(f)[1](CH2=CH2)2CuLi;[2]H2O
See all solutions

Recommended explanations on Chemistry Textbooks

Physical Chemistry

Read Explanation

Organic Chemistry

Read Explanation

Ionic and Molecular Compounds

Read Explanation

Nuclear Chemistry

Read Explanation

Chemical Reactions

Read Explanation

Chemistry Branches

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.

Sign-up for free