Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 12: Q20P (page 354)

Assign R or S stereochemistry to the two chirality centers in isocitrate, and tell whether OH and H add to the Si face or the Re face of the double bond.

Short Answer

Expert verified

H group adds at the Re face of the carbon group

Step by step solution

01

Citric acid cycle

The water can be added reversibly to the-unsaturated carbonyl compounds to give-hydroxyl carbonyl compounds. An addition that is related to a -unsaturated carboxylic acid occurs in a biological way such as the citric acid cycle of food metabolism, where cis-aconitate is converted into isocitrate by the conjugate addition of the water to a double bond.

02

Stereochemistry

The stereochemistry of the two chiral centers in isocitrate is (2S,3R). The -OH group adds to the Re face of the carbon group. The H group adds at the Re face of the carbon group which is as shown:

H group adds at the Re face of the carbon group

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

Question: Grignard reagents undergo a general and very useful reaction with

ketones. Methylmagnesium bromide, for example, reacts with cyclohexanoneto yield a product with the formulaC7H14O . What is the structure of this product if it has an IR absorption at 3400cm-1?

Question: At what approximate positions might the following compounds showIR absorptions?

(f)

In light of the nitrogen rule mentioned in Problem 12-17, what is themolecular formula of pyridine, M+=79?

Where might the following compounds have IR absorptions?

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.
See all solutions

Recommended explanations on Chemistry Textbooks

Chemical Reactions

Read Explanation

Chemistry Branches

Read Explanation

Chemical Analysis

Read Explanation

The Earths Atmosphere

Read Explanation

Organic Chemistry

Read Explanation

Making Measurements

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