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Chapter 5: Q-5-25P (page 280)

The following structures are optically active compounds. Star (*) the asymmetric carbon atoms in these structures.

Short Answer

Expert verified

When four different atoms or groups are attached to the central carbon atom, it is known as asymmetric carbon. The chirality of a structure can be predicted by the presence of an asymmetric center. Though an asymmetric carbon atom is a very important aspect in determining the chirality of a molecule, it is not the only factor determining chirality. Several ring structures also show axial chirality.

Step by step solution

01

Asymmetric carbon

When four different atoms or groups are attached to the central carbon atom, it is known as asymmetric carbon. The chirality of a structure can be predicted by the presence of an asymmetric center. Though an asymmetric carbon atom is a very important aspect in determining the chirality of a molecule, it is not the only factor determining chirality. Several ring structures also show axial chirality.

02

Asymmetric center of the first structure

The asymmetric carbon is marked with an asterisk.

Both structure a and b represent the same molecule. Structure b gives more clarity as it shows that the central carbon is bonded to four different groups. The four different groups are : CH2Br, NH2, CF3 and

03

Asymmetric centre of the second structure’

This structure has two asymmetric carbons marked with asterisk.

04

Asymmetric center of the third structure

This structure has three asymmetric carbons marked with asterisk.

05

Asymmetric center of the fourth structure

This structure has three asymmetric carbons marked with asterisk.

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Most popular questions from this chapter

(+)-Tartaric acid has a specific rotation of +12.0掳. Calculate the specific rotation of a mixture of 68% (+)@tartaric acid and 32% (-)@tartaric acid.

Question: For each pair, give the relationship between the two compounds. Making models will be helpful.

(a) (2R,3S)-2,3-dibromohexane and (2S,3R)-2,3-dibromohexane

(b) (2R,3S)-2,3-dibromohexane (2R,3R)-2,3-dibromohexane

(c)

(d)

(e)

(f)

(g)

(h)

(i)

Question: For each of the compounds described by the following names,

1. draw a three-dimensional representation

2. star (*) each chiral center

3. draw any planes of symmetry.

4. draw any enantiomer.

5. draw any diastereomers.

6. label each structure you have drawn as chiral or achiral

(a) (S)-2-chlorobutane

(b)(R)-1,1,2-trimethylcyclohexane

(c) (2R,3S)-2,3-dibromohexane

(d) (1R,2R)-1,2-dibromocyclohexane

(e) meso-hexane-3,4-diol,CH3CH2CH(OH)CH(OH)CH2 CH3

(f) 卤-hexane-3,4-diol

Question: Draw all distinct stereoisomers for each structure. Show the relationships (enantiomers, diastereomers, etc.) between the isomers. Label any meso iosmers, and draw any mirror planes of symmetry.

(a) CH3 -CHCI-CHOH-COOH

(b) tartaric acid, HOOC-CHOH - CHOH-COOH

(c) HOOC -CHBr-CHOH- CHOH-COOH

(d)

(e)

Question. For each structure,

  1. Draw all the stereoisomers.
  2. Label each structure as chiral or achiral.
  3. Give the relationships between the stereoisomers (enantiomers, diastereomers).
See all solutions

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