name ______________________________
Page 1 of 2
1. Provide all necessary reagents for the following reactions. (9 pts)
C
C
CH3
H2,
Lindlars catalyst
H
H
CH3
1) BH3, THF
2) H2O2, NaOH, H2O
O
H3CH2CH2C C C H
H
a) NaNH2, NH3
b) CH3CH2Br
1-butyne
3-hexyne
2. Assign the stereochemistry of the following: (6 pts)
H2N
CHO
H
CO2H
H
OH
H
OH
CH3
CH2OH
S
R
S
name ______________________________
Page 2 of 2
3. Carefully examine the Fischer projections A-H and answer the following questions (give only one
answer for each question, 10 pts)
A
CHO
B
CHO
OH
HO
H
H
OH
H
OH
HO
H
H
OH
H
OH
HO
H
HO
H
OH
H
OH
CH2OH
CH2OH
HO
H
HO
CH2OH
F
CHO
CHO
CH2OH
G
H
HO
H
HO
OH
HO
H
H
HO
H
CH2OH
CH2OH
D
H
OH
CHO
CH2OH
H
H
E
C
H
CO2H
H
H
OH
H
OH
H
H
H
OH
H
OH
CH2OH
CH2OH
CH2OH
Which Fischer projection (B-H) is the enantiomer of A?
______C______
Which Fischer projection (B-H) is identical to A?
______D______
Which Fischer projection (B-H) is a diastereomers of A?
____B or H____
Which Fischer Projection (B-H) is a constitutional isomer of A?
______H_______
Which Fischer Projection (A-H) is meso?
______F______
____________________________________________________________________________________
Problem 1 (9 pts) _____________
2 (6 pts) _____________
3 (10 pts) _____________
Total (out of 25) ____________