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please answer questions number 1-6

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1. Draw all the isomers of the 2,3-butanadiol compound.
a. From the stereoisomers, determine which one is (if any):
Score:20
enantiomer, diastereomer, and meso! Explain it
b. Draw the Newman projection by looking down the 2,3-bond.
. Which one having the highest and the lowest energy
H
OH
2.
Assign Cahn-Ingold-Prelog rankings to the following sets of
substituents:
Score: 10
(a) -CH-CH2 -CH(CH3)2 -C(CH3)3. -CH2CH3
(b) -C=CH. -CH=CH2. -CICH3/3-
(c) -CO2CH3 -COCH3, -CH2OCH3, -CH2CH3
(d) -CEN. -CH2Br, -CH2CH2Br, Br
3. Assign E or Z configuration to the following alkenes:
Score: 15
(al H3G
CH2OH
(b)
C-C
CI
C=C
CH3CH2 CI
CH30
CH2CH2 CH3
4 ) b .
CHg 50
(c) CH3
CO2H
(d)
H
CN
CH2OH
HaC
"CH2 NH2
COOH
OF OH
H
4. Draw the Fischer's projection of the following compounds:
(Score: 15)
a. 2 (R), 3 (S) -trihydroksibutanal
RUHS() b. Acid 2 (S), 3 (S) -dichlorobutanoate
c. 1, 3 (R), 4 (S), 5-tetrahydroxy-2-pentanone
H
5. Which of the following terms best describes the pair of compounds
(Score: 20)
shown: enantiomers, diastereomers, or the same compound? (5 pairs)
CH
H
O
I
3H
O
H
- CH
1
H
H
OH OF
2
H
H
( 7)3
GOCH
4 ) c. 9 0 cri

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CI
H
Call Br
HIC
Br
-CI
b.
OH
CH3
-OH
C.
CH3
CH2OH
H -OH
HO--H
OH
C H2OH
OH
d.
6. Which is more stable, a 1,2-transdichloro cyclohexane or its cis
isomer? Explain it
(Score: 20)
TABLE 4.2 Steric Strain in Monosubstituted Cyclohexanes
Strain of one H-Y
1,3- diaxial Interaction
(K) /mol)
(kcal/mol)
0.12
$0.25
Br
10.25
OH
0.5
CHE
0.9
CH,CHS
0.95
CH(CHO.
1.1
CICH b
27
CHS
CO.H
C2004 Thomson - Brooks/Cole
OH
N
Col, OH

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