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Tutorial 2. Stereochemistry PDF

1. This document provides a tutorial on stereochemistry, including: identifying chiral and achiral molecules; distinguishing between enantiomers and diastereomers; assigning R/S configurations to asymmetric carbons; drawing 3D structures of stereoisomers; determining the number of asymmetric carbons and identifying meso compounds. 2. Key concepts covered include distinguishing between stereoisomers based on their mirror-image and non-mirror-image relationships, drawing Fischer projections, and labeling asymmetric carbons as either R or S. 3. Examples provide practice in applying these stereochemistry concepts to determine structural and configurational relationships between stereoisomers.

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Matthew Pok
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308 views5 pages

Tutorial 2. Stereochemistry PDF

1. This document provides a tutorial on stereochemistry, including: identifying chiral and achiral molecules; distinguishing between enantiomers and diastereomers; assigning R/S configurations to asymmetric carbons; drawing 3D structures of stereoisomers; determining the number of asymmetric carbons and identifying meso compounds. 2. Key concepts covered include distinguishing between stereoisomers based on their mirror-image and non-mirror-image relationships, drawing Fischer projections, and labeling asymmetric carbons as either R or S. 3. Examples provide practice in applying these stereochemistry concepts to determine structural and configurational relationships between stereoisomers.

Uploaded by

Matthew Pok
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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TUTORIAL 2.

STEREOCHEMISTRY

1. Indicate whether the molecules shown below are chiral or achiral:

a)

OH

OH

b)

H
CH3
C C C
H CO2OH

c)

CH2OH

C
HO2C CO2H
H

d)

Cl

e)

3
O

2. a) Which of the following terms best describes the pair of compounds shown: enantiomers,
diastereomers, or the same compound?

CH3
CO2OH
CO2H H2
C H
H N
NH2 CH3
b)
CH3
H C
OH

HO

3. Label each asymmetric carbon in the compound below as R or S.

a)

OH
CH3

b)

OH
H CH3

H CH3
OH

c)

Cl

4. Draw the structure of (a) (2R,3S)-2,3-dichloropentane, (b) (S)-1-bromo-1-chloropropane and (c) 1,3-
dichlorocyclopentane . Take particular care to indicate three- dimensional stereochemical detail properly.

5. How many asymmetric carbons are present in the compound below?

a)
CH3
b)

HOH2C
HO O
HO OH
OH

c)

CO2H
H OH
H OH
CO2H

d) ethyl-2,2,4-trimethylpentane

6. Can the molecules shown below be properly described as a meso compound?


a)

b)

Cl

Cl

c)

Cl Cl

7. Draw the structure of (1R, 2R)-1-bromo-2-chlorocyclobutane. Take particular care to indicate stereochemistry
properly.

8. Stereoisomers which are not mirror image isomers are .


9. Is it theoretically possible to separate the pair of compounds below by distillation? Explain briefly.

O O

CH3 CH3

Br Br

10. Draw the Fischer projection of (S)-2-hydroxybutanoic acid, CH3CH2CH(OH)COOH.

11. How many enantiomers are there of the molecule shown below?

OH

OH

12. Which of the following terms best describes the pair of compounds shown: enantiomers,
diastereomers, or the same compound?

a)
Cl Cl
H3C H

H CH3
Cl Cl

b)

Br CH3

H H Br
H3C
CH2CH3 CH2CH3

13. Label each asymmetric carbon in the molecule below as having the R or S configuration.

HO2C H
F H

H3C CH2CH3

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