Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 12: Q25E (page 354)

Reaction of acetone with D3O+yields hexadeuterioacetone. That is, all the hydrogens in acetone are exchanged for deuterium. Review the mechanism of mercuric-ion-catalyzed alkyne hydration, and then propose a mechanism for this deuterium incorporation.

Short Answer

Expert verified

An interconversion between two forms occurs in this mechanism, one of which is ketone, and another of which is enol. The hydrogen atom takes part in the interconversion by exchanging with the solvent atom.

Step by step solution

01

Mechanism of mercuric-ion-catalyzed alkyne hydration

An interconversion between two forms occurs in this mechanism, one of which is ketone, and another of which is enol. The hydrogen atom takes part in the interconversion by exchanging with the solvent atom.

02

Mechanism for conversion of acetone into hexadeuterioacetone

In the first step, Addition of D+to the acetone results into a formation of enol and the one from the methyl group displace and one deuterium atom gets attached.

Similarly removal of the hydrogen atom and addition of the deuterium atom takes place and at last there is a formation of an hexadeuterioacetone takes place.

General 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

Predict the product and provide the complete electron-pushing mechanism for the following two-step synthetic processes:

Question: 4-Methyl-2-pentanone and 3-methylpentanal are isomers. Explain how you could tell them apart, both by mass spectrometry and by infrared spectroscopy.


Draw the structure of an alkene that yields only acetone, (CH3)2C=O, on ozonolysis followed by treatment with Zn.

What functional groups might the following molecules contain?

(a) A compound with a strong absorption at 1710 cm-1

(b) A compound with a strong absorption at 1540 cm-1

(c) A compound with strong absorptions at 1720 cm-1 and 2500 to 3100cm-1

Question: The mass spectrum (a) and the infrared spectrum (b) of another unknown hydrocarbon are shown. Propose as many structures as you can.
See all solutions

Recommended explanations on Chemistry Textbooks

Chemical Analysis

Read Explanation

Chemical Reactions

Read Explanation

Organic Chemistry

Read Explanation

The Earths Atmosphere

Read Explanation

Nuclear Chemistry

Read Explanation

Inorganic 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