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1!
Organic Chemistry I Test 2 Extra Stereochemistry Practice Problems
Page 1: Designate R/S Page 2: Chiral or Achiral? Page 3: Same, Enantiomer, or Diastereomer?
A. Designate the R/S configuration for any chiral centers in the following molecules.
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
18.
19.
20.
21.
22.
23.
24.
25.
26.
27.
28.
29.
30.
BrH
HBr
HH2N
BrH
HO
HOH
OHH
HO
OHH
HO
ONH2
HOH
O
HOH
OH
BrH
HO
O O
CH3
H
O O
CH3
H
N
H
O
CH3
H
NH2
OHH
HO
OH
OHH
O
OHH
O
HH3CO
CH3
H
OHH
O
NH2
HCH3
OHH
H2N
OH
H
CH3
Br
CH3CH3
HH
HO
O
H
NH2
H
H
NH2
H3C
H
CH3CH3
HHO
CH3CH3
HH
CH3
HO
H
CH3
H
HOH
O
HH
ClHO
O
H3C
H
O
CH2OHH
H
HO
HO
HHHO
H
OH
This one is very hard.
But for each of the 5 chiral C's, the tie-
breaking processes do work.
The upper-left S is harder than the others.
R,R
R,R, error in movie
which said R, S.
Priorities: 1. Heteroatom. 2. C-with-heteroatom.
3. C > CH > CH2 > CH3.
4. Proceed down chain until point of difference.
Really
Hard!
