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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

Assign Cahn鈥揑ngold鈥揚relog rankings to the following sets of substituents

a.鈭�CH=CH2,鈭�CH(CH3)2,鈭�C(CH3)3,鈭�CH2CH3

b.鈭�CO2CH3,鈭�COCH3,鈭�CH2OCH3,鈭�CH2CH3

c.鈭�CO2CH3,鈭�COCH3,鈭�CH2OCH3,鈭�CH2CH3

d.鈭�CO2CH3,鈭�COCH3,鈭�CH2OCH3,鈭�CH2CH3,鈭�CO2CH3,鈭�COCH3,鈭�CH2OCH3,鈭�CH2CH3

The IR spectrum of phenylacetylene is shown in Figure 12-28. What absorptionbands can you identify?

Draw structures corresponding to the following IUPAC names:

a)cis-1,2-Cyclohexanedicarboxylic acid

b) Hepatanedioic acid

c) 2-Hexen-4-ynoic acid

d) 4-Ethyl-2-propyloctanoic acid

e) 3-chlorophthalic acid

f) Triphenylacetic acid

g) 2-Cyclobutenecarbonitrile

h) m-Benzoylbenzonitrile

Question: At what approximate positions might the following compounds show

IR absorptions?

(c)

Show the structures of the fragments you would expect in the mass

spectra of the following molecules:
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