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

Amino acids can be prepared by reaction of alkyl halides with diethyl acetamidomalonate, followed by heating the initial alkylation product with aqueous HCl. Show how you would prepare alanine, CH3CH(NH2)CO2H, one of the twenty amino acids found in proteins, and propose a mechanism for acid-catalyzed conversion of the initial alkylation product to the amino acid.

Question: Ketones undergo a reduction when treated with sodium borohydride, NaBH4.What is the structure of the compound produced by reactionof 2-butanone with NaBH4 if it has an IR absorption at 3400cm-1andM+=74in the mass spectrum?

Nitriles, R - C = N , undergo a hydrolysis reaction when heated with

aqueous acid. What is the structure of the compound produced by hydrolysis of propanenitrile, CH3CH2C=N , if it has IR absorptions from 2500-3100cm-1 and at 1710cm-1 , and has M+ = 74?

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

Rank the double bonds below in terms of increasing stability:
See all solutions

Recommended explanations on Chemistry Textbooks

Making Measurements

Read Explanation

Nuclear Chemistry

Read Explanation

Organic Chemistry

Read Explanation

Kinetics

Read Explanation

Chemical Analysis

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