Chapter 5

Stereochemistry
Adrian Ferrariski

1406601113
Alfredo
1406601044
Engga Saputra
1406577120
Farid Mujiantono
1406601214
Hendri
1406578142
Jessica Edlyn
1406602721

Classify each pair of compounds as

constitutional isomers or
stereoisomers

a. Constitutional
isomers
b. Constitutional
isomers
c. Constitutional
isomers
d. Stereoisomers

2
a.

b.

Locate any stereogenic center

in the given molecules

c.

d.

e.

f.

3
A.

Locate the stereogenic center in each

compound and draw both enantiomers

B.

C.

Locate the stereogenic centers

in each compound

Untuk menentukan lokasi

stereogenic center, kita dapat
melihatnya dari atom karbon
tetrahedral (sp3) dalam molekul
yang mengikat empat kelompok
atom yang berbeda.

a.

*
*

d.
b.

c.

*
* *

e.

Which group in each pair is

assigned the higher priority

a. CH3

CH2CH3

b. I

Br
c. H
D
d. CH2Br
CH2CH2Br
e. CH2CH2Cl
f. CH2OH

CH2CH(CH3)2
CHO

Rank the following groups in

order of decreasing priority

a. COOH, H, NH2, OH
3

b. H, CH3, Cl,
4

c. CH2CH3,
2

CH2Cl
1

CH3, H, CH(CH3)2
3

d. CH = CH2,

CH3, C CH,
3

Label Each Compound as R or S

2

Counter Clockwise
S isomers

Counter Clockwise
S isomers

4
Counter Clockwise
1. Lihat Ar atom
yang
S isomers
Counter Clockwise
langsung mengikat atom
S isomers
C pusat
2. Jika ada 2 atau lebih
tangan atom C pusat
mengikat langsung atom
yang sama, maka dilihat

Draw all the possible stereoisomers for each

compound and label pairs of enantiomers and
diastereomers

A.

C.

B.

D.

A & B Enantiomer, C & D Identical, AB & CD

Diastereomer

A.

B.

C.

D.

A & B enatereomer, C & D enastereomer, AB &

CD Diastereomer

Which compounds are meso

compounds
b.

a.

Meso
Compound

c.

Not Meso
Compound

Not Meso
Compound
Compound C contains a plane
of symmetry, and is achiral.
Meso compounds generally
contain a plane of symmetry so
that they possess two mirror
image halves.

1
0

Without drawing out the structures, label each

pair of compounds as enantiomers or
diastereomers

a. (2R,3S) 2,3 hexanadiol and

(2R,3R) 2,3 hexanadiol

b. (2R,3R) 2,3 hexanadiol and
(2S,3S) 2,3 hexanadiol
c. (2R,3S,4R) 2,3,4 hexanatriol
and (2S,3R,4R) 2,3,4
hexanatriol
a.Diastereomer
b.Enantiomer
c.Diastereomer

1
1
a.

Draw all possible stereoisomers for each

compound. Label pairs of enantiomers and
diastereomers

b.

c.

1
2
a.

State how each pair of compounds is

related. Are they enantiomers,
diastereomers, constitutional isomers, or
identical

CH3
Br
C

Br

and
H2COH

CH2OH
b.
and

H
CH3

c.
HO

OH

OH

and

OH

d.
OH

OH

and

OH

HO

a. Identical
b. Identical
c. Constitutional
Isomers
d. Diastereomers