Organic Chemistry I Recitation Problem set
Chapter 5: Stereoisomerism
1) Identify the relationship between the following pairs of molecules. Are they the same compound,
structural isomers, or stereoisomers? If they are stereoisomers, are they enantiomers or
diastereomers? Assign R or S configuration to all asymmetric carbons.
a) H C H
3 f)
H C CH Br HO C CH
2 3
HO BrH2C
HO H H OH
b) H3C Br g)
H OH
H C Br H C CH
3
H3CH2C H3CH2C HO H
c) H H3C h)
H3C C Br H C Br
H3CH2C H3CH2C HO H HO H
k) m) OH
OH OH l) OH OH OH
i) CH3 OH
HO H
H3C j)
CH2OH HO
H OH H3C CH3
CH2OH OH
OH
2) Label each asymmetric carbons as R or S on the molecule on the right. How many
possible stereoisomers does this molecule have? How many are enantiomers?
3) Draw Fischer projections of the following molecules. Assign configuration to each stereocenter.
What is the relationship between each molecule (identical, enantiomers, diastereomers,
constitutional isomers, different compound)?
B O H C H O
A OH OH
HO H OH OH
HO HO
OH O
HO OH
OH OH
4) Draw Fischer projections from the following names.
a) (S)-2-hydroxybutanoic acid, CH3CH2CH(OH)COOH.
b) (2R,4R)-2,4-dibromopentane.
c) (2R,3R,4S)-2,3,4-trichloroheptane
5) For the following molecules,
a) Circle all tetrahedral stereogenic centers.
b) Test for chirality (1. Draw the mirror image, 2. Draw any internal planes of symmetry, 3.
Determine configuration of each stereocenter—R or S). Label each compound above as chiral,
achiral, or achiral and meso
1.
Br 3. Br
Br
Br
2. 4.
Br
Br Br
6) Identify each molecule below as chiral, achiral, or achiral and meso. SHOW YOUR WORK (mirror
images, planes of symmetry, R/S configuration)
1. 2. 4.
3. OH
CH2OH
HO2C C CO H
2
OH H
5. 6. 7. CH2OH 8.
H3CH2C H Cl F H OH
SH
C C
H CH2CH3 F H OH
Cl
CH2OH
7) What is the % enantiomeric excess of the following scalemic mixtures?
a) 20% S, 80 % R
b) 13% d, 87% l
c) 33% (+), 67% (-)
d) 5% D, 95% L
8) Calculate the percent of each enantiomer present from the % enantiomeric excess. (How much of it is a
racemic mixture?)
a) 98% ee of R enantiomer
b) 70% ee of (-) enantiomer
c) 30% ee of D enantiomer
9) Would a 50:50 mixture of (2R,3R)-2,3-dibromobutane and (2R,3S)-2,3-dibromobutane be optically
active? Explain.
10) Translate the structure below to a Fischer projection.
11) For the molecules below,
a) Convert each chair projection and Newman projection into a perspective drawing using wedges
and dashes to indicate “up” and “down” substituents on the ring.
b) Indicate configurations of all stereocenters centers with R/S and unsymmetrical double bonds with
E/Z.
c) What is the relationship between the molecule in the box and each structure below? Choose one of
the following:
• not an isomer (different molecular formula)) • structural isomer
• different conformation (same molecule) • enantiomer
• different perspective (same conformation) • diasteriomer
OH
HO Me
perspective (wedge/dash)
1 3 OH H 4
H OH 2 O
H OH HO Me HO H
1 3 OH H 4
H OH 2 HO O
H H H
3HO Me
H
1 OH Me 4
H
Me HOH 2 HOOH H OH H H O
H
H HOH Me HHO Me H
OH H H
Me H
H H H Me
OH H H
Me H
5 OH 6 Me H 7 OH
OH
8
HO H OH
5 OH H 6 Me H 7Me OH
H OH
8 OH
HO OH
5 OHH 6 HMe HH Me
7 OH OH OH
HH OH
OH
8
HO OH
H H Me
H OH
H OH OH
H H
OH
11 12 H OH
9 OH 10 Me OH HO Me H
11 12 H OH
9HO OH 10 Me OH HO
H H
Me OH
H
Me OH H H
HO 11 H O 12H H OH
OH
9 OH 10 Me OH
OH
HO Me
H H H
Me
O
HO H H OH
Me OH H H
O