Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 14: Q 41P (page 747)

Question: Both LiAlH4and Grignard reagents react with carbonyl compounds to give alkoxide ion intermediates (that become protonated in an aqueous workup). Those alkoxides can react with 1o or methyl alkyl halides or tosylates to give ethers. Show how the following ethers can be formed in this two -step process. As starting materials, you may use any reactants containing 8carbons or fewer.

Short Answer

Expert verified

The functional group is which two alkyl groups are bonded to an oxygen atom are known as ethers. Ethers have the general formula R-O-R', where R and R' represent alkyl groups.

Step by step solution

01

Ethers

The functional group is which two alkyl groups are bonded to an oxygen atom are known as ethers. Ethers have the general formula R-O-R', where R and R' represent alkyl groups.

02

Synthesis of ethers

Alkoxide ion intermediates can be formed by the reaction of carbonyl compounds (aldehyde or ketone) with LiAlH4 or Grignard reagents. Alkoxide ion intermediates that are formed can react with methyl alkyl halides or tosylates to give the ethers.

(a)

(b)

(c)

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

(a) Tetramethyloxirane is too hindered to undergo nucleophilic substitution by the hindered alkoxide, potassium tert-butoxide. Instead, the product is the allylic alcohol shown. Propose a mechanism to explain this reaction. What type of mechanism does it follow?

(b) Under mild acid catalysis, 1,1-diphenyloxirane undergoes a smooth conversion to diphenylethanal (diphenylacetaldehyde). Propose a mechanism for this reaction. (Hint: Think Pinacol.)

Rank the given solvents in decreasing order of their ability to dissolve each compound

(a) HCOO-Na+

(b)

(c)


Solvents

Ethyl ether, water, ethanol, dichloromethane

There are two ways of making 2-ethoxyoctane from octan-2-ol using the Williamson ether synthesis. When pure (-) -octan-2-ol of specific rotation -8.240is treated with sodium metal and then ethyl iodide, the product is 2-ethoxyoctane with a specific rotation of -15.60. When pure (-) -octan-2-ol is treated with tosyl chloride and pyridine and then with sodium ethoxide, the product is also 2-ethoxyoctane. Predict the rotation of the 2-ethoxyoctane made using the tosylation/sodium ethoxide procedure, and propose a detailed mechanism to support your prediction.

Question. Give the structures of intermediates A through H in the following synthesis of trans-1-cyclohexyl-2-methoxycyclohexane.

Boron tribromide(BBr3)cleaves ethers to give alkyl halides and alcohols.

The reaction is thought to involve attack by a bromide ion on the Lewis acid-base adduct of the ether with(BBr3)(a strong Lewis acid). Propose a mechanism for the reaction of butyl methyl ether with(BBr3)to give (after hydrolysis) butan-1-ol and bromomethane.
See all solutions

Recommended explanations on Chemistry Textbooks

Inorganic Chemistry

Read Explanation

Physical Chemistry

Read Explanation

Nuclear Chemistry

Read Explanation

Kinetics

Read Explanation

Chemical Reactions

Read Explanation

Ionic and Molecular Compounds

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