/*! 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} Q48P Grignard reagents react slowly w... [FREE SOLUTION] | 91影视

91影视

Log out

Learning Materials

Features

Discover

Chapter 10: Q48P (page 538)

Grignard reagents react slowly with oxetane to produce primary alcohols. Propose a mechanism for this reaction, and suggest why oxetane reacts with Grignard reagents even though most ethers do not.

Short Answer

Expert verified

When Grignard reagent reacts with oxetane, it produces primary alcohol very slowly. There is a cleavage of bonds in the oxetane ring by the Grignard reagent.A new C-C bond is formed.

Step by step solution

01

Grignard reaction with oxetane

When Grignard reagent reacts with oxetane, it produces primary alcohol very slowly. There is a cleavage of bonds in the oxetane ring by the Grignard reagent.A new C-C bond is formed.

02

 Step 2: Mechanism of oxetane with Grignard reagent

The mechanism of the Grignard reagent with oxetane is similar to epoxide cleavage in ethylene oxide by the Grignard reagent. In this, the driving force is the presence of 4-membered cyclic ether, which relieves ring strain. That is why it undergoes a Grignard reaction while most other ethers do not

.

Mechanism of oxetane with 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

Show how you would accomplish the following transformations. You may use any additional reagents you need.

  1. octan-3-ol from hexanal, CH3 (CH 2)4CHO
  2. octan-1-ol from 1-bromoheptane
  3. 1-cyclohexylethanol from acetaldehyde, CH3CHO
  4. 1-cyclohexylethanol from bromocyclohexane
  5. benzylalcohol (ph-CH2-CHO)from bromobenzene (ph-Br)

g. cyclopentylphenylmethanol from benzaldehyde

h. octan-1-ol from 1-bromohexane

Give IUPAC names for the following compounds.

a.

b.

c.

Arrange the following compounds in order of decreasing acidity.

CH3COOH CH3OH CH3CH3 CH3SO3H CH3NH2 CH3SH CH3CCH

Question: Predict the products of the following reactions.

(a)CH3CH2Br+Mg鈫�ether

(b) isobutyliodide+2Li鈫�hexane

(c) 1-bromo-4-fluorocyclohexane+Mg鈫�THF

(d) CH2=CCl-CH2CH3+2Li鈫�ether

Ever since the Grignard reaction was discovered to react with ethylene oxide, chemists have experimented with other epoxides to test the limits of this reaction (which chemists call the scope of the reaction). The conclusion is that the success of the Grignard reaction is limited by the steric hindrance in the epoxide. One group published results of several Grignard reagents on one epoxide; one of their products is shown here. What Grignard reagent and what epoxide were used to make this compound? Comment on the steric requirements of the epoxide and the stereochemistry of the product.
See all solutions

Recommended explanations on Chemistry Textbooks

Inorganic Chemistry

Read Explanation

Ionic and Molecular Compounds

Read Explanation

Nuclear Chemistry

Read Explanation

The Earths Atmosphere

Read Explanation

Organic Chemistry

Read Explanation

Physical 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.