/*! 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} Q16P Propose a mechanism for the reac... [FREE SOLUTION] | 91影视

91影视

Log out

Learning Materials

Features

Discover

Chapter 10: Q16P (page 519)

Propose a mechanism for the reaction of acetyl chloride with phenylmagnesium bromide to give 1,1-diphenylethanol.

Short Answer

Expert verified

When acid chloride is added to 2 equivalents of Grignard reagent in an ether solvent, and after protonation, it forms tertiary alcohol. In acid chlorides, the OH group of the acid is replaced by a Cl atom.

Step by step solution

01

Addition of acid chloride to Grignard reagent

When acid chloride is added to 2 equivalents of Grignard reagent in an ether solvent, and after protonation, it forms tertiary alcohol. In acid chlorides, the OH group of the acid is replaced by a Cl atom.

02

Mechanism for the reaction between an acid chloride and phenylmagnesium bromide

The mechanism shows the nucleophilic substitution, and Cl is the leaving group. It takes place at carbonyl carbon, which is the unusual feature we see in this mechanism.

Mechanism of reaction between an acid chloride and Grignard reagent

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

Predict which member of each pair is more acidic, and explain the reasons for your predictions.

(a) cyclohexanol or 3-chlorophenol

(b) cyclopentanol or cyclopentanethiol

(c) cyclopentanol or cyclopentanecarboxylic acid

(d) pentan-1-ol or 2,2-dichloropentan-1-ol

Predict which member of each pair will be more soluble in water. Explain the reasons for your answers.

(a) hexan-1-ol or cyclohexanol

(b) heptan-1-ol or 4-methylphenol

(c)3-ethylhexan-3-ol or octan-2-ol

(d)hexan-2-ol or cyclooctane-1,4-diol

(e)

Suggest carbonyl compounds and reducing agents that might be used to form the following alcohols.

  1. heptan-1-ol
  2. 1-cyclohexylethanol
  3. 1-phenylpropan-1-ol

e)

f)

Predict the products you would expect from the reaction of NaBH4 with the following compounds. You may assume that these reactions take place in methanol as the solvent

a.CH3(CH2)8-CHO

b.

c. Ph-COOH

d.

e.

f.

Show how you would synthesize the following compounds from alkyl halides, vinyl halides, and aryl halides containing no more than six carbon atoms.

  1. octane
  2. vinylcyclohexane
  3. trans-oct-3-ene
  4. cyclopentyl propyl ketone
See all solutions

Recommended explanations on Chemistry Textbooks

Making Measurements

Read Explanation

Chemical Analysis

Read Explanation

The Earths Atmosphere

Read Explanation

Chemistry Branches

Read Explanation

Kinetics

Read Explanation

Organic 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.