Stereochemistry Exam Preparation Pack

Answer Key- Advanced

note - all problems can also be found here (link)
Section A: Find Chiral Centers and Determine R/S
Find the chiral centers in each of these molecules with “alternative
uses” and determine R/S for each chiral center. Link to answer
https://bit.ly/3F2e8Sc

R
R R
R
S
S

Cocaine LSD

R
R

R S S
R R

THC Heroin

Section B: Convert to Fischer Projection

For each of the three molecules below:

• Label each chiral center as R/S
• Convert the drawing into a Fischer projection
• Draw the other stereoisomers as Fischer projections
• Indicate which of these stereoisomers is the enantiomer
• Indicate which stereoisomer(s) are diastereomers

Stereochemistry Answer
Key - Advanced
1 https://www.masterorganicchemistry.com
 B-1 2,3-Dibromosuccinic acid https://bit.ly/2WjbAxm

no enantiomer (meso!) other stereoisomers (both diastereomers)

B-2 2,3-Dichlorobutane https://bit.ly/3AUeGXJ

Fischer projection Enantiomer Diastereomer (meso!)

B-3 3-Chlorobutan-2-ol https://bit.ly/3kKhoJH

Fischer projection Diastereomer Diastereomer Enantiomer

Section C: Chiral or Achiral Molecules?

C-1 Chiral or achiral molecules? https://bit.ly/2XWI5lm
If meso, indicate

achiral chiral chiral achiral

meso meso

Stereochemistry Answer
Key - Advanced
2 https://www.masterorganicchemistry.com
 C-2 Chiral or achiral molecules? If meso, indicate
https://bit.ly/3CSBO9E

achiral chiral

achiral meso chiral

C-3 Chiral or achiral molecules? Indicate if meso
https://bit.ly/3zKH64Z
achiral

achiral

achiral
achiral
meso
C-4 Chiral or achiral molecules? Indicate meso (if present)
https://bit.ly/3um8DJd

chiral achiral

chiral chiral

Stereochemistry Answer
Key - Advanced
3 https://www.masterorganicchemistry.com
 D-1 Draw the enantiomer (+ more) https://bit.ly/3uhaBdK
Your mission is to:
1) identify all chiral centers in
Zocor
2) Draw the enantiomer
3) How many stereoisomers
are possible for Zocor?

*
*

* * *
*
*
Zocor enantiomer
27 stereoisomers possible

E-1 Enantiomers, Diastereomers, Constitutional Isomers,

or the Same? https://bit.ly/3AX3iuo
For each pair: Are these molecules enantiomers,
diastereomers, the same, or constitutional isomers?
Would an equal mixture of these two compounds
rotate plane-polarized light?

a) same a) enantiomers
b) yes b) no

a) same
b) no

Stereochemistry Answer
Key - Advanced
4 https://www.masterorganicchemistry.com
 E-2 Enantiomers, Diastereomers, Constitutional Isomers, or
the Same? https://bit.ly/3AQwAe1
a) same
b) no

a) diastereomers
b) yes

a) same
b) yes

E-3 Enantiomers, Diastereomers, Constitutional Isomers, or

the Same? https://bit.ly/2WlZPX9

a) same
b) no

a) enantiomers
b) no

a) same
b) yes

Stereochemistry Answer
Key - Advanced
5 https://www.masterorganicchemistry.com
 E-4 Enantiomers, Diastereomers, Constitutional Isomers, or
the Same?
https://bit.ly/3zVJGpa

a) enantiomers
b) no

a) diastereomers
b) yes

a) enantiomers
b) no

E-5 How are these three molecules (A, B, and C) related to

each other? https://bit.ly/3zVJOVG

A B C

A and B: same
A and C: diastereomers
B and C: diastereomers
Section F: Given the name, draw the structure
a) Draw (2S,3R)-2,3-Difluorohexane using wedge/dash
b) Draw the diastereomers https://bit.ly/39OwBTT

2S, 3R 2R, 3R 2S, 3S 2R, 3S

diastereomer diastereomer (enantiomer)

Stereochemistry Answer
Key - Advanced
6 https://www.masterorganicchemistry.com
 Section G, H, I: Cycloalkanes https://bit.ly/3kPVbtM
G-1 a) Draw the two achiral forms of 1,3,5-Trimethylcyclohexane
b) Which is more stable?

achiral #1 most stable achiral #2 most stable

chair form chair form
(most stable overall)

H-1 https://bit.ly/3kPPDzv
a) Draw the most stable achiral isomer of a cyclohexane with a
single fluoro and a single bromo substituent on the ring
b) Draw the most stable chiral isomer of a cyclohexane with a
single fluoro and a single bromo substituent on the ring

achiral most stable chiral most stable

chair form chair form

I-1 a) Draw one version of 1,3-Dimethylcyclohexane that is chiral, and

one that is achiral https://bit.ly/3ATf6gZ
b) One of these isomers has two conformers of very different energy.
Draw those two chair conformations.

chiral achiral achiral has conformers of very

different energy

Stereochemistry Answer
Key - Advanced
7 https://www.masterorganicchemistry.com
 J-1 Draw The Enantiomer (+ more) https://bit.ly/3kQpoZW
Escitalopram (Celexa):

enantiomer
• Pure S enantiomer shows a specific rotation of +120°. Sven, a
worker in the quality control unit, observed a specific rotation of –30°
for a test sample. What is the percentage of (R) and the percentage
of (S) in that sample?
62.5 % (R) 37.5 % (S)

K-1 Optical Activity https://bit.ly/2Wl9EV7

An 80:20 mixture of the (R,R) and (S,S) enantiomers of 2,3-dibro-
mobutane has an optical rotation of –30°.
Using these templates, show the stereochemical representation of
these compounds, their stereoisomers, and their optical rotations:

2R, 3R 2S, 3S 2R, 3S

[ a ]: –50° [ a ]: +50° [ a ]: 0° C

Stereochemistry Answer
Key - Advanced
8 https://www.masterorganicchemistry.com
 L-1 Resolution https://bit.ly/39IRIa2
Draw the two products of the following reaction, clearly showing stereochemistry
(it’s OK to use “R3N” for (+)-brucine). Note that (+/–) implies a 1:1 mixture of en-
antiomers.
Racemic mixture of mandelic acid: reaction with (+)-Brucine

(+)-mandelic acid (–)-mandelic acid

• How are these products related to each other? diastereomers
• How might you exploit this to resolve mandelic acid into its
enantiomers? Describe this process briefly

1) add (+)-brucine to racemic mixture. 2) recrystallize, and

separate crystals (one diastereomer) from mother liquor,
which contains other diastereomer. 3) add acid to crystals,
re-forming mandelic acid, then extract in separatory funnel
using water and organic solvent to separate optically active
mandelic acid from the salts (can do the same for the mother
liquor)
M-1 Chiral Nitrogens https://bit.ly/3zNGV99
Although the nitrogen in the molecule A below has four different
substituents, the nitrogen does not give rise to a pair of enantio-
mers. Why not?
Would you expect the nitrogen in molecule B to be a chiral center?
Why or why not?

constrained geometry; inversion is

disfavored.
nitrogen is a chiral center

A B
inverts rapidly, can’t
be separated
Stereochemistry Answer
Key - Advanced
9 https://www.masterorganicchemistry.com