Drills on Stereochemistry

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A. Identifying chiral center.

1. In each of the compounds below, indicate the chiral center with an asterisk ( ), and label
the four groups from 1 to 4 using the system of priorities based on atomic number.
a) b) c) d)

2. Build models of cis-1,2-dichlorocyclopentane and trans-1,2-dichlorocyclopentane.

a. Identify the chiral centers in each.
b. Classify each molecule as chiral or achiral. If you have trouble deciding, build models of
the mirror images and see if they are superimposable.
Drills on Stereochemistry Organic Chemistry for Engineering

B. Determine the R and S configuration of the following molecules

a) b) c)

________ ________ ________

d) e) f)

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 ________ ________ _______

C. Enantiomers and Diastereomers

a. Build a model of CH2BrCl. Next, build a model of the mirror image of your first molecule.
How are these models related?

b. Build a model of CHBrClF. Next, build of model of the mirror image of your first molecule.
How are these molecules related?

c. Consider the molecule

Drills on Stereochemistry Organic Chemistry for Engineering

i) How many stereoisomers are possible? Recall: the maximum number of stereoisomers
is equal to 2n, where n = number of stereogenic centers.
ii) Draw each of the possible stereoisomers.
iii) Identify pairs of enantiomers, pairs of diastereomers and meso compound, if any.

C. Fischer Projection
1. For each compound below, determine the configuration (R or S) of every stereocenter. Then
draw the enantiomer of each compound.
a) b) c) d)

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