Professional Documents
Culture Documents
Assigning R & S Configurations 3. Diastereomers - Molecules With Two or More Stereocenters
Assigning R & S Configurations 3. Diastereomers - Molecules With Two or More Stereocenters
Chapter 3
Chapter 3:
Page 1 of 21
C341/Spring 2010
Chapter 3
(R)-limonene
Orange smell
(S)-limonene
Lemon smell
Page 2 of 21
C341/Spring 2010
Chapter 3
Page 3 of 21
C341/Spring 2010
Chapter 3
We will discuss in a moment that chiral carbons have two forms R & S
Page 4 of 21
C341/Spring 2010
Chapter 3
CHOLESTEROL
TAXOL- Taxol, a potent anticancer natural product (with activity against a number of
leukemias and solid tumors in the breast, ovary, brain, and lung in humans) was isolated from
the bark of the pacific yew in 1971.
Page 5 of 21
C341/Spring 2010
Chapter 3
Aspartame
Neotame
Page 6 of 21
C341/Spring 2010
Chapter 3
Naproxen Sodium
Page 7 of 21
C341/Spring 2010
Chapter 3
Page 8 of 21
C341/Spring 2010
Chapter 3
2.
A.
b. If priority cannot be assigned based solely on atomic number, then look at the
next atom attached. Priority is assigned by the first point of difference.
B.
Orient the molecule in space so that the lowest priority is directed away
from you.
C.
C341/Spring 2010
Chapter 3
O
OH
OH
OH
OH
OCH 3
Cl
Cl
OH
OH
OH
Page 10 of 21
C341/Spring 2010
Chapter 3
F
NH2
NH2
More practice:
COOH
*
Ketoprof en
Page 11 of 21
C341/Spring 2010
Chapter 3
Page 12 of 21
C341/Spring 2010
Chapter 3
Fischer Projections
Fischer projections are used usually when molecules have more than one chiral
center in the backbone. They impart three dimensional information in a two
dimensional method.
o A & B are
o C & D are
o A & C, A & D are
o B & C, B & D are
Page 13 of 21
C341/Spring 2010
Chapter 3
Page 14 of 21
C341/Spring 2010
Chapter 3
How many stereoisomers do you expect for the following molecule? How many
enantiomers and how many diastereomers?
CHO
H
Cl
Br
OH
CH3
Page 15 of 21
C341/Spring 2010
Chapter 3
For example:
CH 3
H
Br
CH 3
1
CH 3
CH 3
Br
Br
Br
Br
CH 3
CH 3
3
Page 16 of 21
CH 3
H
Br
Br
Br
H
CH 3
4
C341/Spring 2010
Chapter 3
Page 17 of 21
C341/Spring 2010
Chapter 3
Br
Page 18 of 21
C341/Spring 2010
4.
Chapter 3
Are enantiomers identical in physical properties? Can you ever tell them apart
when you prepare them?
o Enantiomers have identical physical properties, i.e. the same melting point,
boiling point, and solubility in standard solvents.
o Diastereomers do have different properties since they may have different
dipole moments and different IMF.
Page 19 of 21
C341/Spring 2010
Chapter 3
Optical Activity
One property that DOES exist that is different between enantiomers is their
optical activity. (Discovered in 1811 by Francois Arago and Jean Baptiste Biot).
Enantiomers rotate polarized light in equal but opposite directions.
Polarimeter:
Page 20 of 21
C341/Spring 2010
Chapter 3
When chemists run a reaction, do they always end up preparing a mixture that
is 50:50 mixture of each enantiomer?
Racemic mixture =
Page 21 of 21