Ch 5 :

stereoisomerism
↳
Isomers w/ same connectivity between atoms but
different 3D , spatial arrangement of their atoms

Double Bonds 4 Rings

f- C cannot rotate 02 diff isomers :
CIS 4 trans
bc of IT bond

•
Are following us ,
trans ,
or neither ?
H

/ OH H

↳
H 't
H -
ft
- Hofuf
it trans
l
CIS CIS H neither
one can be equatorial no 2 isomers

{ one axial but don't matter

cause both on top

Chirality * a chiral molecule is not the same as its mirror image

-

if you can lay a molecule on top of another =

same molecule
=
not isomers
OH
I
OH
l
Et ' ' ' '

I
-
H H Jati , Et
NIT super imposable
Me 1 Me

Chirality Center :
carbon forms tetrahedral center will different groups attains

Iq chiral center
AI chiral center
join H

4 diff groups OH I ta-

double bond makes

u
.

attached to carbon a difference

a-
Identify all chirality centers ( if any) :

CH , CH , CH , CH,

hit
!
"

Ho H
l t it neither
Hf l H ,c ca,
, H
I
CH,
H

H CH,
not chiral
 Enantiomers :
mirror images but not super imposable

¥!
non super imposable
-

oooo
mirror image
(R) ( s)

" " " "

Cahn -

Ingold -

Pre log :
names enantiomers R or S
right left

1. using atomic #s , prioritize 4 groups

'
'
It
'
attached to chirality center ¥ chiral center Cl
y
2.
arrange so lowest priority group
do
BY
Faces away from you "
3
to
3. count
group priorities 1 2 -3
. . .

determine whether order goes 0 or O

4 Clockwise
.
R counterclockwise
= = S

① ①
To R
It? # ④
clockwise

1¥ ¥*
-1
•
ex o
-
-

→
"
" .

HZN ⑤ $ of
" 3

2
¥1 '

②
①
Cl ④ ④ " IT " ①
* when 2 identical atoms are attached to
→ %nH " "
first atom breaks tie
1¥ ' Hs
chiral center ,
non -
identical
s
←
z *
not sum ,
first point ( atom)

Ra -

chirality center =
R * if doublet triple bond =
atom counts 213 times

-
Determine R vs .
S

¥9 ! } !
① Cl ④
roam
it
R trick : =

Kyoto
.

( : ③←
,

② R S
 "
•
Consider a cyclohexane w/ 3 substituents #
stereoisomers :
2 N: # of
stereo centers

I when I wedge be all combinations

* no dash =
could

- mirror images
a-

✓ ←
all poss combthat
K 9
diff
23
motel
=
8

-
* If we consider these 2 =
diaster comers
bc Cl not flipped

•
What is Max # of stereoisomers ?
C# z

CH ,
CHS )
H

' H If u switch a chiral

28 Max stereoisomers It will be diff molecule
256

* In order for molecule to be chiral , it must be non -

superimpossible
w/ mirror image
chiral center =
4 diff things attached
CH , CH, ICH ,

x
¥1
--
€4 °

any molecule w/ internal mirror plane =

achiral
I a- mirror
trans CIS
CH ,
not chiral Meso compound =
molecules w/ even # Of chirality
chiral
•
f centers 4 a mirror plane
have less than predicted 2N Isomers

* to be chiral , a compound cannot be a rotational conformer of its mirror image

 Chair flip

O
O
O O

* chair becomes *
not chiral
own mirror image by chair flipping

super imposable = same molecule

meso F

- - - -

int . mirror }
plane

chair flip :
bond rotations =
not 2 Isomers

Identify all chiral centers :

¥
/

1 OH
H
( ff -
R
Z R Rz
3

d-
C
z
I
C C
N
°
- V O H
⑥ "
" H
C H
3
CHS H H
 ( mirror image) ( not mirror)
•
Are these enantiomers or diastercomers ? both not super imposable

"
" I was enantiomer
k
ii.

Iv I
£✓ ✓ II
'
'
'
'

diastereomers

OH
diastereoisomers
Cl p
X be not mirror
images
"
A-
'
" "
"l s, H
'
H H

diastereoisomers

neither

Identify plane of symmetry :

•
draw all poss stereoisomers :

- a
Which is enantiomer

:
select all diastereoisomers

Which can exist as meso ?

What is the relationship between two structures :

Identical

Enantiomers

Diaster corners
 Diaster corners

Enantiomers

same Compound

same compound

•
Identify plane of symmetry
:

/ :
'
l
Cl Cl

Constitutional

Diaster corners
•
Identify whether chiral or achiral ?

-
-
✓ Chiral
chiral chiral achiral

l l
,
I \
achiral
achiral / achiral \ chiral

•
Draw stereoisomers of 1,4 -

dimethyl cyclohexane :

pi 1B each isomer is achiral

in A so neither has an enantiomer
1 y y y
3

I
z

v.
⑥

•
Compound is chiral ,
draw enantiomer :

chiral bc not superimposable

on mirror image

•
What is the config .
Of stereo center ?

C
2 I
•
Identify relationship :

QH
OH =

¥ ¥ Identical

Enantiomers

•
Assign configuration :

CC H
Z H
z
R
H