1
Draw this molecule in both chair forms and then circle the one that is the favored.
Ph
HO
CH3
Br
Draw the Newman conformation for the following molecule exactly as drawn
sighting down the indicated carbons. Then draw the other 5 conformations in
order by rotating the front carbon counterclockwise. Label each conformation as
anti, gauche, eclipsed or worst eclipsed.
sight down Carbons
4-5 with 4 in front
Br
2
1
4
6
3
5
H
7
Phenyl is the largest group on
carbon 4. t-Butyl is the largest
group on carbon 5
2
E. In the following pairs, label them as the same molecule, enantiomers or
diastereomers.
H2N
H
H
NH2
a. ____________________
H
H
OH
H3C H
OH
Br H
b. ____________________
H3CH2C
Br
H3CH2C
CH3
(2R,3R)-2,3-dichloropentane and
(2S,3R)-2,3-dichloropentane
c. ____________________
d. ____________________
e. ____________________
f. ____________________
3
Give the R and S for each of the following stereocenters in the following molecules.
Label the groups 1-4.
H OH
H3C F
Cl
H H
F
H
O
Br
F
OH
Draw this molecule in both chair forms and then circle the one that is the favored.
Ph
5
6
4
1
HO
3
2
CH3
Br
Ph
OH
CH3
1
6
2
4
6
5
3
Ph
4
Br
HO
5
2
1
3
Br
CH3
4
Draw the Newman conformation for the following molecule exactly as drawn
sighting down the indicated carbons. Then draw the other 5 conformations in
order by rotating the front carbon counterclockwise. Label each conformation as
anti, gauche, eclipsed or worst eclipsed.
sight down Carbons
4-5 with 4 in front
Br
2
1
4
Phenyl is the largest group on
carbon 4. t-Butyl is the largest
group on carbon 5
6
3
5
7
H
Ethyl
Br
Ph
Ethyl
Ph Ethyl
Ph
Propyl
H
t-butyl
Propyl
GAUCHE
H
Br
t-butyl
Eclipsed
Propyl Ethyl
H
t-butyl
Br
ANTI
Br Ethyl
ethyl
Propyl
H
Ph
Propyl
Br
t-butyl
Eclipsed
Br
H
t-butyl
H
Propyl
Ph
t-butyl
Ph
GAUCHE
Worst Eclipsed
5
In the following pairs, label them as the same molecule, enantiomers or
diastereomers.
H2N
H
H
NH2
DIASTEREOMERS
a. ____________________
H
H
OH
H3C H
OH
Br H
ENANTIOMERS
b. ____________________
H3CH2C
Br
H3CH2C
CH3
(2R,3R)-2,3-dichloropentane and
(2S,3R)-2,3-dichloropentane
DIASTEREOMERS
DIASTEREOMERS
c. ____________________
DIASTEREOMERS
d. ____________________
SAME MOLECULE
SAME MOLECULE
e. ____________________
ENANTIOMERS
f. ____________________
6
Give the R and S for each of the following stereocenters in the following molecules.
Label the groups 1-4.
S
3
1
H
H OH
H H
2
c
d
2
F
3
d
4
O
S
2
F
1
b
Cl
S
1
S
3
c
a
b
R
4
2
a
b
3
Br OH
a
c
1
4
H3C F
4
R
S
7
H
Br
Br
H
H
H
Br
Cl
H
I
Br
Br
H3 C
Cl
Cl
Cl
H
I
H
Br
H
Cl
Cl
F
F
Br
F
Cl
I
F
Br
(2R, 3R, 4S, 5R)
(2S, 3S, 4R, 5S)
Cl
H
I
8
SAME
ENANTIOMERS
H
Br
Br
H
SAME
H
H
Br
Cl
H
Cl
Cl
I
Br
Br
H3C
Cl
H
DIASTEREOMERS
I
H
Br
H
DIFFERENT CMPDS
Cl
Cl
F
F
ENANTIOMERS
Br
F
Cl
I
DIASTEREOMERS
F
Br
(2R, 3R, 4S, 5R)
(2S, 3S, 4R, 5S)
Cl
H
I
ENANTIOMERS
9
OH
Br
H
OH
HO CH2CH3
H3C
H
H3C OH
Br
OH
OH
ENANTIOMERS
DIASTEREOMERS
Br
H
HO CH2CH3
H3C
H
H3C OH
DIASTEREOMERS
Br
SAME MOLECULE
SAME MOLECULE
10
1. Draw the structure for the following using bond-line formula structure.
a. 4-sec-butyl-3-fluoro-5-isopropyl-6-cyclobutyl-2,4-nonadien-1-ol
b. 4-fluoro-3-ethyl-2-methoxy-1,3-cyclohexadiene
2. Write the correct name for the following.
11
3. Draw the Newman conformation for the following molecule exactly as drawn sighting down the indicated
carbons, carbon 4 is the front carbon and carbon 5 is the back carbon. Then draw the other 5 conformations
in order by rotating the front carbon clockwise.
4. Draw this molecule in both chair forms and then circle the one that is the favored.
12
5. In the following pairs, label them as the same molecule, different conformations of the same molecule,
different molecules, enantiomers or diastereomers.
6. Label the following as R or S on every stereocenter below(label 1,2,3,4).
Br
Cl
H
Br
I
Cl
CH3
H
H
H
13
6.
14
1. Draw the structure for the following using bond-line formula structure.
a. 4-sec-butyl-3-fluoro-5-isopropyl-6-cyclobutyl-2,4-nonadien-1-ol
b. 4-fluoro-3-ethyl-2-methoxy-1,3-cyclohexadiene
2. Write the correct name for the following.
5-tert-butyl-6-chloro-8-fluro-3,7-nonadien-1-ol
bicycle[4.2.2]decan-7-ol
15
3. Draw the Newman conformation for the following molecule exactly as drawn sighting down the indicated
carbons, carbon 4 is the front carbon and carbon 5 is the back carbon. Then draw the other 5 conformations
in order by rotating the front carbon clockwise.
4. Draw this molecule in both chair forms and then circle the one that is the favored.
16
5. In the following pairs, label them as the same molecule, different conformations of the same molecule,
different molecules, enantiomers or diastereomers.
6. Label the following as R or S on every stereocenter below(label 1,2,3,4).
17
6.
indicate if the following are enantiomers, diastereomers or same molecule in different conformation
Br
OH
Cl
H 3C
CH3
Br
Cl
SAME
HO
CH3
DIASTEREOMERS
SAME
ENANTIOMERS
Br
H
1
OH
F
H
S
2
3
F
2
S
OH
Br
1
SAME
3