EXERCISE STEREOCHEMISTRY

(CHM3201 SEM 1 2011/2012)

1. Draw the structural formula and give the IUPAC name for the following compounds:

a) cis-CH3CH2CH = CHCH2CH3
b) trans-(CH3)2CHCH=CHCH(CH3)2
c) (R)-2-chlorobutane
d) (S)-3-chloro-1-pentene
e) (Z)-2-bromo-2-pentene
f) (3Z,6E)-1,3,6,-octatriene
g) (2R,3R)-2,3-hexanediol

2. Give the complete name of the compounds below including their stereochemistry:
OH
CH3 O
Cl CH3
i. CH3CH2CHCH2-C-OCH2CH3 ii.
CH(CH 3)2

CH(CH 3)2
H3C H
iii.
iv. (H 3C) 2HC
H CH3
HO
H

OH
CH3 O
Cl CH3
i. CH3CH2CHCH2-C-OCH2CH3 ii.
CH(CH 3)2

CH(CH 3)2
H3C H
iii.
iv. (H 3C)2HC
H CH3
HO
H

3. Consider the molecules with molecular formula C2H2Br2Cl2.

a) Draw a structure that is optically inactive because it does not have an
asymmetric center.
b) Draw a structure that is optically inactive because it is a meso compound.
c) Draw a structure that is optically active because it is chiral.

4. Consider the molecule, 3-chloropropanoic acid. Draw the 3 staggered and 3 eclipsed
conformers for the 360o rotation around the C2-C3 bond.

5. Assign priorities to the following pairs of groups according to Cahn-Ingold-Prelog :

a) CH3- , CH3CH2-
b) (CH3)3C- , (CH3)2CH-
c) (CH3)2CH , CH2=CH-
d) - CH(OH)CH3 , -OH, - COOH, -CH2OH
e) - CH2NH2, -NO2, -CN, -NH2

1
6. Draw and determine the R and S configuration of pairs of enantiomers (if any) for
the following compounds:

a) 3-Bromohexane d) 3-Chloro-3-methylpentane
b) 1,2-Dibromo-2-methylbutane e) 1,3-Dichloropentane
c) 3-Methyl-3-pentanol f) 3-Methylhexanoic acid

7. Determine the configurations (R or S) of the following molecules and convert their

structures to Fisher projections:

H CH2OH Cl H
H CH3
a C
c
C C
H3C OH
HOH2C OH

Br
H3C
b
C

HOH2C H

8. Assign R and S configurations to each chirality centre in the molecules below.

CHO CH3
a b
H c
CN C

H COOH
H Cl Br

CH2Br
OH
d
C
H3C COOH
H

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9. Label all chiral carbons (if any) in the following molecules:

O CH3

a. b. c. d. O
OH Cl
Cl

e. (CH3)2CHCHBrCH3 f. CH3CH2CH2CHOH(CH3)
g. H2NCH(CH3)COOH h. CH3CHBrCHBrCH3
i. CH3CH2CH2CH(CH3)2 j. CH2=CHCHBrCH3

10. Draw and determine the R and S configuration of pair of enantiomers (if any)
from the following compounds:

a) 3-Bromohexane b) 3-Chloro-3-methyl-pentane
c) 1,2-Dibromo-2-methylbutane d) 1,3-Dichloropentane
e) 3-Methyl-3-pentanol f) 3-Methylhaxanoic acid

11. Convert the following structures into Newman projections:

HO H
Br Cl H
CH2OH H CH3 OH
a. H b. H3C c. d. HOH2C CH3
H3C OH HOH2C H HOH2C H
OH
12. Draw all the possible stereoisomers for the following compounds:

a) 2-Methyl-2,3-pentadiol b) 3,4-Diaminopentanal
c) 3,4-Dichlorohexane d) 4-Methyl-3-hexanol

For every stereoisomers, label all chiral carbons and determine their R or S
configurations. Indicate pairs of enantiomers, diastereomers and meso compounds.

13. In a chlorination of propane experiment, four products (A, B, C and D) with

molecular formula C3H6Cl2 have been isolated. What are their structures?

a. Each one of the product was further chlorinated and the number of trichloro
products (C3H5Cl3) from each were determined by gas chromatography. A
gave only one trichloro, B gave two trichloro, C and D each gave three
trichloro products. What are the structures for A, B, C and D?

b. By using other synthetic method, C was found to be optically active. What is

the correct structure for C and D.

14. What are the relationships (enantiomers, diastereomers, meso compound or

identical isomers) amongst the following molecules?

3
 CH3 CH3
COOH NH2
a. H2N H HOOC H H2N COOH
H CH3 H3C COOH NH2 H

H H CH3 OH
b. HO CH2CH3 HO CH3 HO H H3C H

H OH HO H H OH H3CH2C H

CH3 CH2CH3 CH2CH3 OH

H H Br Br
c. H3CH2C Br H CH2CH3 H CH2CH3
H3CH2C Br

Br H H3CH2C H Br H H CH2CH3

CH2CH3 Br CH2CH3 Br

Cl CH2CH3 Cl
H
d. H H CH3
H3CH2C H H H
Cl CH2CH3
Cl CH3 H3CH2C Cl
H CH3 Cl CH3
CH3
Cl H
15. Draw all the possible Fisher projecdtion of 2,3-pentandiol. Label pairs of
enantiomers, diastereomers and meso compounds (if applicable).