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Stereochemistry Worksheet Lab

This document is a stereochemistry worksheet that contains questions about: 1) Labeling stereoisomers in molecules 2) Assigning R/S configuration to stereocenters 3) Providing examples of stereoisomer types 4) Drawing chiral molecules with multiple stereocenters 5) Completing stereochemical reactions and determining product relationships 6) Drawing mechanisms for stereochemical reactions involving substitution, elimination, and addition.

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Daniel McDermott
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815 views3 pages

Stereochemistry Worksheet Lab

This document is a stereochemistry worksheet that contains questions about: 1) Labeling stereoisomers in molecules 2) Assigning R/S configuration to stereocenters 3) Providing examples of stereoisomer types 4) Drawing chiral molecules with multiple stereocenters 5) Completing stereochemical reactions and determining product relationships 6) Drawing mechanisms for stereochemical reactions involving substitution, elimination, and addition.

Uploaded by

Daniel McDermott
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
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Stereochemistry Worksheet Lab

Section #
TA Name

Student Name
Student ID

1. Label (by circling or marking with an asterisk) all the stereoisomers on the following molecules. Note: you
cannot label absolute configuration (R or S) on the given structures since there is no wedge/dash scheme.
HN
B.

A.
H
N

F3C
Cl
Fluoxetine

Cl
HO

Setraline

C.

O
HO
O

F
O
Triamcinolone acetonide

2. Label the following compounds as having R or S configuration around the stereocenter(s).


HO H
1 2

Br
1
H

AcO H

H OH

1
H

H
Br

Br

OH

OTs

2
OH

F
Cl H

3. Give an example of:


a. A compound with two or more stereocenters that is superimposable on its mirror image.

b. A pair of compounds that are chiral but are non-superimposable and non-mirror images.

c. A pair of compounds with 2 or more stereocenters that are non-superimposable and mirror
images.

4. Draw the following compounds


a. (2S,5R)-5-chloro-2-ethylhexanoic acid

b. (1R,2R,4R)-4-ethylcyclohexane-1,2-diol

c. (2S,3R)-3-amino-2-phenylbutanal

d. (1S,2S,3R)-2-fluoro-3-propylcyclobutanol

e. (2E, 7Z)-5-bromo-2,7-nonadiene

5. For the following reactions:


a. Complete the reactions with both possible chiral products.
b. Determine and label the absolute configuration (R or S) of all stereocenters.
c. Label the reaction type and the stereochemical relationship (meso, enantiomer, diastereomer, or
none).
Starting
material

Reagents

Products

type

OsO4

H 2O

D2, Pd/C

MeOH

H 3O

Ph

HCl
Ether

OH

heat

Cl

Br2
CH2Cl
2

d. For reactions 5c through 5f, draw the reaction mechanism showing lone pairs, arrows, bond
making/breaking, etc. for each reaction.
3

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