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Chapter 5: Q56 E_b. (page 148)

Identify the indicated faces in the following molecules as Re or Si:

(a)

(b)

Short Answer

Expert verified

(b)

Step by step solution

01

Re or Si face

There are two planar faces in a compound, with a prochiral hybridized group designated Re and Si faces.The ‘Re’ face is clockwise, and the ‘Si’ face is anticlockwise. The Si face can be obtained by flipping the molecule.

02

The faces in the crotonate molecule

(b) According to C.I.P. sequence order, ‘Re’ face is given to the lower planar face, which is clockwise. ‘Si’ face is given to the upper planar face, which is anticlockwise.


Re and Si faces in crotonate

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Most popular questions from this chapter

The first step in the metabolism of glycerol, formed by digestion of fats, is phosphorylation of the pro-R -CH2OHgroup by reaction with adenosine triphosphate (ATP) to give the corresponding glycerol phosphate plus adenosine diphosphate (ADP). Show the stereochemistry of the product.

Draw both cis- and trans-1,3-dimethyl cyclohexane in their more stable chair conformations.

(a) How many stereoisomers are there of cis-1,3-dimethyl cyclohexane, and how many of trans-1,3-dimethyl cyclohexane?

(b) Are any of the structures chiral?

(c) What are the stereochemical relationships among the various stereoisomers of 1,3-dimethyl cyclohexane?

Erythronolide B is the biological precursor of erythromycin, a broadspectrumantibiotic. How many chirality centers does erythronolide Bhave? Identify them.

Orient each of the following drawings so that the lowest-ranked group is toward the rear, and then assign R or S configuration

Ketones react with sodium acetylide (the sodium salt of acetylene,Na+-:C≡CH) to give alcohols. For example, the reaction of sodium acetylide with 2-butanone yields 3-methyl-1-pentyn-3-ol

(a)Is the product chiral?

(b)Assuming that the reaction takes place with equal likelihood from both Reand Sifaces of the carbonyl group, is the product optically active? Explain.
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