Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 17: 17-54P (page 847)

A racemic mixture of 2-methyl-1-phenyl-1-butanone is formed when (R)-2-methyl-1-phenyl-1-butanone is dissolved in an acidic or basic aqueous solution. Give an example of another ketone that undergoes acid- or base-catalyzed racemization.

Short Answer

Expert verified

For racemization, we need a ketone with an carbon that is asymmetric in nature. For example:

Step by step solution

01

Acid or base catalyzation of (R)-2-methyl-1-phenyl-1-butanone

A ketone having carbon results in the formation of enol by the acid or base catalysis losses the asymmetric center. After some time, the enol reforms the ketone again with an asymmetric center and forms the S-2-methyl-1-phenyl-1-butanone.

02

Acid or base catalyzation of 4-Methyl-3-oxo-hexene

4-Methyl-3-oxo-hexene, on acid or base catalyzation, gives the racemic mixture of R and S molecules.

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

In the presence of excess base and excess halogen, a methyl ketone is converted to a carboxylate ion. The reaction is known as the haloform reaction because one of the products is haloform (chloroform, bromoform, or iodoform). Before spectroscopy became a routine analytical tool, the haloform reaction served as a test for methyl ketones: the formation of iodoform, a bright yellow compound, signaled that a methyl ketone was present. Why do only methyl ketones form a haloform?

Use retrosynthetic analysis to plan a synthesis of the following target molecules. The only carbon-containing compounds available for the syntheses are cyclohexanol, ethanol, and carbon dioxide.

(a)

(b)

(c)

(d)

There are other condensation reactions similar to the aldol and claisen condensations:

a. The Perkin condensation is the condensation of an aromatic aldehyde and acetic anhydride. Draw the product obtained from the following Perkin condensation:

b. What compound is formed if water is added to the product of a Perkin condensation?

c. The Knoevenagel condensation is the condensation of an aldehyde or a ketone that has no alpha- hydrogens and a compound such as diethyl malonate that has an alpha-carbon flanked by two electron- withdrawing groups. Draw the product obtained from the following Knoevenagel condensation:

d. What product is obtained when the product of a Knoevenagel condensation is heated in an aqueous acidic solution?

When the enzymatic decarboxylation of acetoacetate is carried out inH218O, all the acetone that is formed contains18O. What does this tell you about the mechanism of the reaction?

Which of the following compounds will decarboxylate when heated?
See all solutions

Recommended explanations on Chemistry Textbooks

Inorganic Chemistry

Read Explanation

Ionic and Molecular Compounds

Read Explanation

Kinetics

Read Explanation

Physical Chemistry

Read Explanation

Organic Chemistry

Read Explanation

Chemistry Branches

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