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Chapter 5: Q.10 (page 185)

Locate the stereogenic centers in each compound.

a.

b.

Short Answer

Expert verified

a.

b.

Step by step solution

01

Stereogenic centers

The point that gives rise to stereoisomers on the interchange of any two substituents attached to it is termed chiral centers or stereogenic centers.

Generally, in molecules involving carbon atoms, the stereogenic centers are the sp3hybridized carbon atom bonded to four different groups of atoms.

02

Stereogenic centers in cholesterol

The cholesterol molecules consist of eight chiral carbon centers and therefore have eight stereogenic centers

Stereogenic centers in cholesterol

03

Stereogenic centers in simvastatin

The simvastatin molecule consists of seven chiral carbon atoms and thus has seven stereogenic centers. The blue circles represent the stereogenic centers.

Stereogenic centers in simvastatin

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Most popular questions from this chapter

a. Locate the stereogenic centres in the ball-and-stick model of lisinopril, a drug used to treat high blood pressure.

b. Label each stereogenic centre as R or S.

Rank the following groups in order of decreasing priority.

  1. -F,-NH2,-CH3,-OH
  2. -CH3,-CH2CH3,-CH2CH2CH3,-(CH2)3CH3
  3. -NH2,-CH2NH2,-CH3,-CH2NHCH3
  4. -COOH,-CH2OH,-H,-CHO
  5. -Cl,-CH3,-SH,-OH
  6. -C≡CH,-CH(CH3)2,-CH2CH3,-CH=CH2

Compare the physical properties of the three stereoisomers of 1,3-dimethylcyclopenatane.

  1. How do the boiling points of A and B compare? What about A and C?
  2. Characterize a solution of each of the following as optically active or optically inactive: pure A; pure B; pure C; an equal mixture of A and B; an equal mixture of A and C.
  3. A reaction forms a 1:1:1 mixture of A, B, and C. If this mixture is distilled, how many fractions would be obtained? Which fractions would be optically active and which would be optically inactive?

Without drawing out the structures, label each pair of compounds as enantiomers or diastereomers.

a. (2R,3S)-hexane-2,3-diol and (2R,3R)-hexane-2,3-diol

b. (2R,3R)-hexane-2,3-diol and (2S,3S)-hexane-2,3-diol

c. (2R,3S,4R)-hexane-2,3,4-triol and (2S,3R,4R)-hexane-2,3,4-triol

Compounds E and F are two isomers of 2,3-dibromopentane drawn in staggered conformations. Which compounds (A–D) in Figure 5.8 are identical to E and F?
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