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Chapter 5: Q5-56-E_a (page 148)

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

Short Answer

Expert verified

In stereochemistry, prochirality is converting achiral compounds into chiral ones. There are two faces in prochirality, one is Re face, and the other is Si face.Re face is when priority groups are arranged clockwise, and Si face is when priority groups are arranged anticlockwise.

Step by step solution

01

Prochirality

In stereochemistry, prochirality is converting achiral compounds into chiral ones. There are two faces in prochirality, one is Re face, and the other is Si face.Re face is when priority groups are arranged clockwise, and Si face is when priority groups are arranged anticlockwise.

02

The faces in the pyruvate molecule

a) According to C.I.P. sequence order, Re face is when priority substitutents are arranged in clockwise order. When we turn over the molecule, the priority substituents become anticlockwise, this is Si face. The 鈥楻e鈥� face is given to upper planar face. Here, the carbonyl group is given 1st priority, followed by anion which is given 2nd priority, and the 3rd priority is given to group. The 鈥楽i鈥� face is given to lower planar face which is anticlockwise.

Re and Si faces in pyruvate

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Most popular questions from this chapter

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

(a)

(b)

What is the stereochemical configuration of the enantiomer of (2S,4R)-2,4-octanediol? (A diol is a compound with two-OH groups.)

Draw examples of the following:

(a) A meso compound with the formula

(b) A meso compound with the formula

(c) A compound with two chirality centers, one R and the other S

Draw the meso form of each of the following molecules, and indicate the plane of symmetry in each:

(a)

(b)

(c)

One of the steps in fat metabolism is the hydration of crotonate to yield 3-hydroxybutyrate. This reaction occurs by addition of 鈥揙H to the Si face at C3, followed by protonation at C2, also from the Si face. Draw the product of the reaction, showing the stereochemistry of each step.
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