CHEM220 Organic Chemistry

Stereochemistry Tutorial

Section A

1. Choose a molecule from that given below which has an asymmetric centre.

A) C(CH3)3OH B) (CH3)2CHOH C) CH3CH2OH D) CH3CH2CH(CH3)OH

2. Which of the following compounds has an asymmetric center?

3. If an object can be superimposed on its mirror image it is said to be

A) chiral
B) achiral
C) a diastereomer
D) an enantiomer

4. Which of the following objects is most likely to be chiral

A) an A4 sheet of paper
B) a stackable bar stool
C) a coffee mug
D) your right foot

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5. Choose the enantiomer of the compound below.

6. Choose the correct enantiomer of the following molecule from the list below.

NH2
CH2CH3
C
H OH

a. OH b. NH2
H H
C C
H2CH3C NH2 HO CH2CH3

c. CH2CH3 d. NH2
H H
C C
H2N OH H3CH2C OH

7. Choose the correct Fischer projection of the following molecule from the list below:

NH2
CH2CH3
C
H OH

a. NH2 b. NH2 c. OH d. OH

H3CH2C H H CH2CH3 H2N CH2CH3 H3CH2C H

OH OH H NH2

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8. Which of the following groups has the highest priority using the Cahn, Ingold, Prelog
rules?

9. If a compound rotates the plane of polarization of plane polarized light, that compound is
said to be

a. achiral
b. mesomeric
c. a trans isomer
d. chiral

10. Which of the following is/are optically inactive?

A) a 50-50 mixture of R and S enantiomers

B) a racemic mixture
C) every achiral compound
D) a meso compound
E) all the above

11. If a compound rotates the plane of polarized light to the left, it is denoted by the symbol

a. (+)
b. (-)
c. R
d. S

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12. A sample of enantiomerically pure (S)-(+)-2-bromobutane has a specific rotation of
+30.0°. A sample containing the two isomers has an observed specific rotation of
+23.1°. This means that:

a. The R-(+)- isomer is in excess

b. The S-(+) isomer is in excess
c. The R-(-) isomer is in excess
d. The S-(-) isomer is in excess

13. An enantiomerically pure sample of (S)-(+)-2-hydroxybutane has a specific rotation of

32.8°. A 100 g sample of a mixture of isomers has an observed specific rotation of 8.2°.
Which one of the following statements is correct?

a. The mixture contains 32.8 g of the S isomer and 67.2 g of the R isomer
b. The mixture contains 87.5 g of the S isomer and 12.5 g of the R isomer
c. The mixture contains 12.5 g of the S isomer and 87.5 g of the R isomer
d. The mixture contains 62.5 g of the S isomer and 37.5 g of the R isomer

14. The specific rotation of a pure substance is 1.68°.

What is the specific rotation of a mixture containing 75% of this isomer and 25% of the (-)
isomer?

A) + 0.42º B) 0º C) + 0.84º D) + 1.26º E) +1.68º

15. Which of the statements below correctly describes an achiral molecule?

A) The molecule exhibits optical activity when it interacts with plane-polarised light.
B) The molecule might be a meso form.
C) The molecule has an enantiomer
D) The molecule has a non-superimposable mirror image
E) none of the above.

16. The following statement holds true for meso compounds:

a. They are stereoisomers that are enantiomers

b. They are diastereoisomers that are enantiomers

c. They contain a stereogenic centre but are unable to rotate the plane of polarization of
plane polarized light

d. They contain a stereogenic centre and rotate the plane of polarization of plane
polarized light

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17. What is the relationship between the following compounds?

18. The following description satisfies that of a constitutional isomer

A) isomers which differ in the way their atoms are connected

B) isomers which differ in the way their atoms are arranged in space
C) isomers that contain asymmetric centres
D) isomers that have a cis/trans relationship

19. Choose the term that best describes the pair of enantiomers from the list given below.

CH3 CH3

H OH HO H

H2N H H NH2

CH3 CH3

a. erythro enantiomers
b. threo enantiomers
c. meso compounds
d. configurational isomers

20. Identify the meso compound from the molecules below:

a. H3 C b. CH3
OH H
HO C C H H C C OH
H CH3 HO CH3

c. H3 C OH d. H 3C H
H C C H HO C C H
HO CH3 HO CH3

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Section B

1 Define the following terms: (3)

(i) stereocentre

(ii) dextrorotatory compound

(iii) diastereomers

2 Fill in the missing words : (3)

A molecule that has a non-superimposable mirror image is said to be _____________.

An _____________centre is the carbon atom that is bonded to four different groups.

_________________ are stereoisomers that are not mirror images of each other (not
enantiomers).

3 Identify two stereogenic centres in the following molecule.

Place an asterisk (*) next to each atom to indicate a stereogenic centre. (2)

OH

HO

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4 Using the template below, draw the enantiomer of the following molecule A.
(1)
NH2
A OH CH3
C C
H3C Cl

Label the molecule A above as either R or S. (1)

5 Answer the questions based on the following molecule. (4)

CH3
C NH2
H Cl

(i) Name the compound according to the R, S configuration.

Show your working.

(ii) Draw its enantiomer

(iii) If the pure sample above has a specific optical rotation of + 27.5°, calculate
the enantiomeric excess of a sample with an observed optical rotation of
+14.7°.

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6 If pure S-(+)-lactic acid has a specific rotation of +40.0° and a sample of S-lactic acid
has an observed specific rotation of +10.0°, determine the percentage of S-(+)-lactic
acid in the sample. (3)

7 (i) Using the Fischer projection, draw all stereoisomers for the following
compound and indicate which are erythro, threo and enantiomers. (4)

CH3CHCHCH3
Cl NH2

(ii) Draw the perspective formula for either of the erythro enantiomers. (1)

8 How many stereoisomers can you get with a molecule that has three stereocentres. (1)

9 Answer the following questions based on 2,3-dichlorobutane. (5)

CH3CHCHCH3
Cl Cl

(i) How many stereoisomers does the molecule have?

(ii) Draw the Fischer projections of these stereoisomers and label which are erythro,
which are threo and which are enantiomers.

(iii) Draw the perspective formula of the erythro structure.

10 How would you separate a pair of enantiomers? (2)

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