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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

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Most popular questions from this chapter

Predict the product(s) and provide the mechanism for each reaction below. What does each mechanism have in common?

b.

c.

d.

Predict the products of the following polar reaction, a step in the citric acid cycle for food metabolism, by interpreting the flow of electrons indicated by the curved arrows:

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?

Rank the double bonds below in terms of increasing stability:

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

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