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stereochemistry note. organic chemistry students
Typology: Exercises
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H 3
C
CH 3 H 3
C CH 3
CH 3
n-butane isobutane
structural isomers
CH 3
H 3
C
(
)
-limonene
CH 3
H 3
C
(
Stereochemical isomers
"orangy taste" "lemony taste"
Figure 1
3
3
σ
n
3
3
3
3
1,
n
n
Group of Low Symmetry
Yes
No
1
s
i
Group of High
Symmetry
d
h
h
∞ v
∞ h
Yes
No
Highest Order
Rotational Axis
n
Perpendicular
2
Axes
Yes
No
C or S groups D groups
σ
h
Yes
No
σ
d
No
n
nd
nh
σ
h
No
Yes
nh
σ v
No
2n
nv
Yes Yes
nv
No
n
Figure 2
Cl
Me Me
Cl
Me Me
mirror
Cl
Me Et
Cl
Et Me
Cl
Et Me
Cl
Me Et
2-Chloropropane
2-Chlorobutane
all groups align
therefore, molecules are
superimposable
two groups fail to align
therefore, molecules are
nonsuperimposable
Cl
Me Me
Cl
Me Me
Figure 3
x 100
x 100
3
3
3
3
cis -but-2-ene trans -but-2-ene
Figure 4
3
3
3
3
3
3
cis -4- tert -butylcyclohexanol
trans
tert -butylcyclohexanol
3
3
3
3
3
3
Figure 5
3
3
3
3
cis -2,3-dimethyloxirane
3
3
trans -2,3-dimethyloxirane
Achiral compound Chiral compound
σ
Figure 6
s s t t
e e
r r
e e
o o gg
e e
n n i i
c c
c c
e e
n n t t
r r
e e
≡
≡
i i
s s
c c h h
e e
r r pp
r r
o o j j
e e
c c t t i i
o o
n n
o o
n n d d
s s
a a b b
o o
v v
e e
t t
h h
e e p p
l l
a a
n n
e e
o o
f f p p
a a p p
e e
r r
o o
n n d d
s s b b
e e l l
o o
w w
t t h h
e e
p p
l l
a a
n n
e e
o o
f f p p
a a p p
e e
r r
Figure 8
Ph COOH
Ph H
Ph
3
3
3
3
H Ph
Figure 9
Ph
3
3
H Ph
3
3
3
3
H Ph
Eclipsed Staggered
60° rotation
1
2
2
1 1
2
Figure 10
3
3 3
3 3
r r
o o t t
a a t t i i
o o
n n
e e
c c l l i i pp
s s
e e d d
s s
t t
a a gg gg
e e
r r
e e
d d
Figure 11
1
2
1
2
Fi scher pro j
ection
Br
2
5
3
Br
3
2
5
180° rotation of C 2
2
1
Br
2
5
3
Br
3
2
5
Br
3
2
5
Br
3
2
5
Sawhorse pro j
ection
Figure 3
1
2
1
2
1
2
1
2
2
1
2
Line of sight
from C 1
to C 2
through C 1
2
Figure 3
2
D-glyceraldehyde
2
L-glyceraldehyde
Figure 4
2
D-glucose
2
L-arabinose
2
D-Mannose
2
D-Xylose
Figure 5
3
2
2
3
2
2
2
2
2
2
2
3
2
2
Br
3
2
3
2
break and duplicate
becomes
becomes
becomes
becomes
break and duplicate
break and duplicate
break and duplicate
becomes
Br
2
3
1
3
1
3
Br
3
1
becomes (C)
Br
3
3
3
Br
2
3
3
Br
2
3
Br R
3
2
3
Br
2
3
3
1
-7-bromo-3-methyloct-1-en-3-ol
Cl
2
2
3
3
2
Cl
3
2
2
2
3
-3-chlorohexane (
-3-chlorohexane