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Worksheets

Stereochemistry

Total questions: 20

Worksheet time: 18mins

Name
Class
Date
1.

What is the relationship between the compounds?

a)

unrelated

b)

enantiomers

c)

diastereomers

d)

conformational isomers

e)

constitutional isomers

2.

Choose the compound that is a constitutional isomer of this compound:

a)
b)
c)
d)
3.

What is the relationship between the compounds:

(3S,4R)-4-methylheptan-3-ol

and

(3R,5S)-5-methylheptan-3-ol

a)

unrelated

b)

enantiomers

c)

diastereomers

d)

conformational isomers

e)

constitutional isomers

4.

What is the relationship between the compounds:

(3S,5R,8S)-8-chloro-5-methyldecan-3-ol

and

(3R,5S,8S)-8-chloro-5-methyldecan-3-ol

a)

unrelated

b)

enantiomers

c)

diastereomers

d)

conformational isomers

e)

constitutional isomers

5.

What is the relationship between the compounds?

a)

same compound

b)

enantiomers

c)

diastereomers

d)

conformational isomers

e)

constitutional isomers

6.

What is the relationship between the compounds?

a)

unrelated

b)

enantiomers

c)

diastereomers

d)

conformational isomers

e)

constitutional isomers

7.

What is the relationship between the compounds?

a)

unrelated

b)

enantiomers

c)

diastereomers

d)

conformational isomers

e)

constitutional isomers

8.

What is the relationship between the compounds?

a)

same compound

b)

enantiomers

c)

diastereomers

d)

conformational isomers

e)

constitutional isomers

9.

What is the relationship between the compounds?

a)

same compound

b)

enantiomers

c)

diastereomers

d)

conformational isomers

e)

constitutional isomers

10.

Assume all you know about a compound is that the name is (+)-d-glucose and select all true statements. (i.e., do NOT look up information about the structure. Use the name only.)

a)

It is chiral.

b)

It has one chiral center.

c)

The enantiomer rotates plane-polarized light counterclockwise.

d)

It has three diastereomers.

e)

It rotates plane-polarized light clockwise.

11.

What is the relationship between the compounds?

a)

same compound

b)

enantiomers

c)

diastereomers

d)

conformational isomers

e)

constitutional isomers

12.

Select the true statement.

a)

These compounds are enantiomers.

b)

These compounds are diastereomers.

c)

The compounds are not enantiomers because they both have the S configuration.

d)

The compounds are not enantiomers because they both have the R configuration.

13.

Select ALL meso compounds.

a)
b)
c)
d)
e)
14.

To determine the R/S configuration, the groups attached to a chiral center would go in this order for highest priority (1) to lowest (4). Listed 1-2-3-4.

a)

Br, ethyl, isopropyl, methyl

b)

methyl, ethyl, isopropyl, Br

c)

Br, ethyl, methyl, isopropyl

d)

Br, isopropyl, ethyl, methyl

15.

Select ALL compounds that are chiral.

a)
b)
c)
d)
e)
16.

You have a 75:25 mixture of (S)-3-bromohexane and (R)-3-bromohexane, respectively. Select the true statement.

a)

The enantiomeric excess is 50%.

b)

The enantiomeric excess is 75%.

c)

The enantiomeric excess is 25%.

d)

It is a racemic mixture.

17.

You have a sample of decan-2-ol that is a mixture of the two enantiomers with 95:5 relative abundance S:R. Select the true statement.

a)

The sample will rotate plane-polarized light clockwise because S is more abundant and S always rotates the light clockwise.

b)

The sample will rotate plane-polarized light counterclockwise because S is more abundant and S always rotates the light counterclockwise.

c)

The sample will rotate plane-polarized light but you cannot know the direction without running the experiment.

d)

The sample will not rotate plane-polarized light.

18.

What is the maximum number of configurational isomers for the line structure shown?

a)

2

b)

4

c)

8

d)

16

19.

This compound has:

a)

No enantiomer and two diastereomers.

b)

One enantiomer and two diastereomers.

c)

Two enantiomers and no diastereomers.

d)

One enantiomer and one diastereomer.

20.

What is the relationship between 1,4-dichlorobutane and 1,6-dichlorohexane?

a)

unrelated

b)

enantiomers

c)

diastereomers

d)

conformational isomers

e)

constitutional isomers