/*! 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} Q36. Question:聽Outline two different... [FREE SOLUTION] | 91影视

91影视

Log out

Learning Materials

Features

Discover

Chapter 22: Q36. (page 911)

Question:Outline two different ways that butan-2-one can be prepared from a nitrile and a Grignard reagent.

Short Answer

Expert verified

Answer

Step by step solution

01

Step-by-Step Solution Step 1: Reaction of nitriles with Grignard reagents

Nitriles react with Grignard reagents to form a compound with a new C-C bond and a ketone group. The alkyl or aryl group of the Grignard reagent acts as the nucleophile and attacks at the electrophilic carbon of the cyanide group.

The mechanism for the reaction with the Grignard reagent is given below:

Reaction with Grignard reagent

02

 Preparation of butan-2-one

The structure of butan-2-one is given below:

butan-2-one

You can prepare butan -2-one from a nitrile and a Grignard Reagent in two ways. The

retrosynthetic analysis is shown below:

Retrosynthetic analysis of butan-2-one

Thus, the synthetic pathway based on the nitriles and Grignard reagents obtained is as follows:

Synthesis of butan-2-one

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

Compelling evidence for the existence of a tetrahedral intermediate in nucleophilic acyl substitution was obtained in a series of elegant experiments carried out by Myron Bender in 1951. The key experiment was the reaction of aqueous with ethyl benzoate C6H5COOCH2CH3labelled at the carbonyl oxygen with 18O. Bender did not allow the hydrolysis to go to completion, and then examined the presence of a label in the recovered the starting material.

He found that some of the recovered ethyl benzoate no longer contained a label at the carbonyl oxygen. With reference to the accepted mechanism of nucleophilic acyl substitution, explain how this provides evidence for a tetrahedral intermediate.

What ester and Grignard reagent are needed to prepare each alcohol?

a.

b.

c.

Draw the product formed when each organometallic reagent is treated with H2O.

Identify the lettered compounds in the following reaction scheme. Compounds F, G, and K are isomers of molecular formula C13H18O. How could 1HNMR spectroscopy distinguish these three compounds from each other?

Question: What carboxylic acid and alcohol are needed to prepare each ester by Fischer esterification?

a.

b.

See all solutions

Recommended explanations on Chemistry Textbooks

The Earths Atmosphere

Read Explanation

Organic Chemistry

Read Explanation

Chemical Reactions

Read Explanation

Physical 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.