BACH2113 Kinetics, Mechanisms and Stereochemistry

Tutorial 3 – Stereochemistry (Part 1)

1. Important keys
-
- Absolute configuration
- Configurational isomers
- R and S configuration
- D and L configuration
- E and Z configuration
- Constitution isomers
- Stereoisomers
- Asymmetric/chiral/stereo-center
- Achiral
- Optically active
- Specific rotation
- Plane-polarized light
- Polarimeter
- Racemate
- Racemic mixture
- Fischer projection
- Enantionmers
- Geometric isomers
- Meso compounds
- Plane of symmetry
- Relative configuration
- Resolution of racemic mixture
- Regioselective and Stereoselective
- Stereospecific
- Syn- and anti-addition
2.

2. Which of the following objects are chiral:

(i) Screwdriver
(ii) A screw
(iii) A bean stalk
(iv) A shoe
(v) A hammer

3. Which of the following compounds are optically active?

CHBr2Cl, BHFCl, CH3CHCl2, CHFBrCl, BeHCl

4. Assign R or S configurations to each chiral center in an ascorbic acid.

5. Name each of the following compounds using R, S, E and Z designations where necessary.

6. A 1.50 g sample of caniine, the toxic extract of poison hemlock, was dissolved in 10 mL of ethanol
and placed in a sample cell with a 5.0 cm pathlength. The observed rotation at the sodium D line was
+1.21. Calculate []D for coniine.

7. A sample of pure (S)-2-butanol was placed in a 10.0 cm polarimeter tube. Using the D line of a
sodium lamp, the observed rotation at 20 C was α = +104. The density of this compound is 0.805
gmL-1. What is the specific rotation of (S)-2-butanol?

8. Calculate the observed rotation of a solution of 0.5245g of (S)-1-amino-1-phenylethane diluted to a

volume of 10.0 mL with methanol at 20 C, using the D line of a sodium lamp and a 1.00 dm tube.
Specific rotation of this material: [α]D23 = -30.0.
9. Draw a tetrahedral representation of (R)-2-chlorobutane.
Assign priorities to the following sets of substituents:
(i) –H, -Br, -CH2CH3, -CH2CH2OH
(ii) –COOH, -COOCH3, -CH2OH, -OH
(iii) –CN, -CH2NH2, -CH2NHCH3, -NH2
(iv) –Br, -CH2Br, -Cl, -CH2Cl

10. Draw structural formula for each of the following compound, clearly showing all aspects of the
stereochemistry.

(i) Z-3,7-dimethyl-2,6-octadien-1-ol

(ii) R-4-methyl-4-phenylcyclohex-2-enone

(iii) (7S, 8R)-7,8-epoxy-2-methyloctadecane

(iv) E-2-methyl-2-buten-1-ol

(v) (2Z, 4E)-2-chlorohexa-2,4-diene

11. Indicate whether each of the following pairs of compounds are identical or are enantiomers,
diastereomers or constitutional isomers:

12. Draw all possible stereoisomers of cyclobutane-1,2-dicarboxylic acid, and indicate the
interrelationships. Which, if any, are optically active? Do the same for cyclobutane-1,3-
dicarboxylic acid.

13. (i) With suitable examples differentiate between the terms “diastereoisomer” and “enantiomers”.
(ii) Compare and contrast the properties of optical and of geometric isomers.