Logout Open In App
Open In App
Warning: foreach() argument must be of type array|object, bool given in /var/www/html/web/app/themes/studypress-core-theme/template-parts/header/mobile-offcanvas.php on line 20

Chapter 21: 35P (page 817)

How would you use a protecting group to carry out the following transformation?

Short Answer

Expert verified

Any chemical compound used in the modification of the reacting compound in order to specify the site of chemo-selectivity is known as the ‘protecting groups.’

Acetals are used as the protecting group of carbonyl compounds.

Step by step solution

01

Protecting group

Any chemical compound used in the modification of the reacting compound in order to specify the site of chemo-selectivity is known as the ‘protecting groups.’

Acetals are used as the protecting group of carbonyl compounds.

02

Acetal group

The given compound has two reactive functional groups among which ketone is more reactive than the ester group.

Therefore, the carbonyl group is converted into an acetal group as follows,

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

Design a stepwise synthesis to convert cyclopentanone and 4-bromobutanal to hydroxy aldehyde A.

Draw a stepwise mechanism for the following reaction, a key step in the synthesis of the anti-inflammatory drug celecoxib (trade name Celebrex).

Besides the tert-butyldimethylsilyl ethers introduced in Chapter 20, there are many other widely used alcohol protecting groups. For example, an alcohol such as cyclohexanol can be converted to a methoxy methyl ether (a MOM protecting group) by treatment with base and chloromethyl methyl ether, . The protecting group can be removed by treatment with aqueous acid.

a. Write a stepwise mechanism for the formation of a MOM ether from cyclohexanol.

b. What functional group comprises a MOM ether?

c. Besides cyclohexanol, what other products are formed by aqueous hydrolysis of the MOM ether? Draw a stepwise mechanism that accounts for formation of each product.

Draw a stepwise mechanism for the following reaction, a key step in the synthesis of conivaptan (trade name Vaprisol), a drug used in the treatment of low sodium levels.

What Wittig reagent and carbonyl compound are needed to prepare each alkene? When two routes are possible, indicate which route, if any, is preferred.

a.

b.

c.
See all solutions

Recommended explanations on Chemistry Textbooks

Chemical Analysis

Read Explanation

The Earths Atmosphere

Read Explanation

Inorganic Chemistry

Read Explanation

Kinetics

Read Explanation

Ionic and Molecular Compounds

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.

Sign-up for free