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Chapter 5: Q-5-29P (page 280)

Convert the following Fischer projections to perspective formulas.

Short Answer

Expert verified

(a)

(b)

(c)

(d)

Step by step solution

01

General concept

The Fischer projection looks like a cross, with the asymmetric carbon atom at the point where the line cross. The horizontal lines are taken to be wedges i.e., bonds that project out towards the viewer. The vertical lines are taken to project away from the viewer, as dashed lines.

02

(a), (b), (c)

Hold the molecule so that,the chiral center (i.e C) is on the plane of the paper,two bonds are coming out of the plane of the paper and are on a horizontal plane,the three remaining bonds are going into the plane of the paper and are on a vertical plane.

03

(d)

Hold the molecule so that the two chiral centers (i.e., C) are on the plane of the paper, four bonds are coming out of the plane of the paper and are on a horizontal plane, and the two remaining bonds are going into the plane of the paper and are on a vertical plane.

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Most popular questions from this chapter

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).

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) ±-hexane-3,4-diol

(+)-Tartaric acid has a specific rotation of +12.0°. Calculate the specific rotation of a mixture of 68% (+)@tartaric acid and 32% (-)@tartaric acid.
  1. Make a model of each compound, draw it in its most symmetric conformation, and determine whether it is capable of showing optical activity.
  1. 1-bromo-1-chloroethane
  2. 1-bromo-2-chloroethane
  3. 1,2-dichloropropane
  4. Cis-1,3-dibromocyclohexane
  5. Trans-1,3-dibromocyclohexane
  6. Trans-1,4-dibromocyclohexane.

2.Star (*) each asymmetric carbon atom in part (1), label each as (R) or (S) and compare your result from part (1) with the prediction you would make based on the asymmetric carbons.

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)
See all solutions

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