CHEM 210 [CHAPTER 5: STEREOCHEMISTRY – STEREOISOMERS

Skills you must master for Chapter 5:

1. Know the difference between isomeric types
2. Be able to draw all possible stereoisomers for a compound and indicate the interrelationships.
3. Learn how to apply these skills to cyclic compounds

Isomerism:

Problem 1: Determine whether the following molecules are identical, constitutional isomers, enantiomers or
diastereomers.

a. b.

c. d.

e. f.

g. h.

i. j.

k. l.

m. m.

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Problem 1: Continued.

n. o.

p. q.

r. s.

t. u.

v. w.

x. y.

z. aa.

bb. cc.

dd. ee.

ff. gg.

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Problem 2: Draw all stereoisomers for the following molecules; indicate the stereochemical interrelationships for all
possible pairs.

Problem 3: Menthol is a member of the terpene family of natural products. It exists in a (1R,2S,5R) form and a (1S,2R,5S)
form. Draw the two molecules in their most stable chair conformer(s). Are these two compounds enantiomers or
diastereomers ?

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KEY
Problem 1:

a. diastereomers b. enantiomers

c. enantiomers d. diasteromers

e. diastereomers f. diastereomers

g. diastereomers h. Identical - (3R,4S)-3,4-dimethylhexane

i. Constitutional isomers j. Constitutional isomers

k. diastereomers l. identical

m. enantiomers m. diastereomers

n. identical o. identical

p. identical q. identical

r. enantiiomers s. identical

t. enatiomers u. diastereomers

v. enantiomers w. diastereomers

x. enantiomers y. enantiomers

z. identical aa. diastereomers

bb. constitutional isomers cc. diastereomers

dd. enantiomers ee. Constitutional isomers

ff. diastereomers gg. diastereomers

Problem 2:

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Problem 3:

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