Chemistry 321
50-Minute Examination #2
Wednesday, October 15, 2003
ANSWERS
1. [5 pts.] Give the correct IUPAC name of the compound in the table below corresponding to digit D of
your BLUGOLD:
0 or 1
2 or 3
4 or 5
6 or 7
8 or 9
Br
OH
Br
OH
OH
Br
OH
HO
Br
Br
0 or 1: E-4-bromo-3-methyl-3-penten-1-ol
2 or 3: Z-4-bromo-3-methyl-3-penten-1-ol
4 or 5: Z-3-bromo-4-methyl-2-penten-1-ol
6 or 7: E-4-bromo-3-methyl-2-penten-1-ol
8 or 9: Z-3-bromo-4-methyl-2-penten-1-ol
2. [5 pts.] Draw the structure of the compound below corresponding to digit C of your BLUGOLD:
0 or 1: Z-3-fluorocyclohexanol
4 or 5: E-4-fluorocyclohexanol
8 or 9: E-4-fluorocyclohexanol
2 or 3: E-2-fluorocyclohexanol
6 or 7: Z-4-fluorocyclohexanol
3. [5 pts.] Draw the lowest energy conformation of the compound in Question 2 corresponding to digit G
of your BLUGOLD.
4. The synthesis of 1-bromo-1-methylcyclohexane from Z-2-methylcyclohexanol proceeds through the
following sequence of compounds:
OH
Me
OH2
Me
H
Me
Me
Me
Br
(a) [5 pts.]
BLUGOLD digit E: 0-4: What is the highest-energy intermediate in this reaction?
BLUGOLD digit E: 5-9: What is the lowest-energy intermediate in this reaction?
(b) [10 pts.] Draw a fully-labeled reaction potential energy profile (reaction coordinate diagram) for the
reaction. Your diagram should show the location and relative energy of every transition state and
intermediate. PAY PARTICULAR ATTENTION TO THE RELATIVE ENERGIES OF ALL SPECIES
INVOLVED
Cl
slow
fast
fast
D
D
D
(c) [5. pts] Draw the mechanism of this reaction by using the appropriate curly arrows and other needed
reactant species [5 pts].
5. [5 pts. each] Complete the following reactions by drawing the structure of the final product, using the
starting compound based on your BLUGOLD nimber as specified.
ALKENES:
0 or 1
2 or 3
(a) BLUGOLD digit F
alkene
(b)BLUGOLD digit D
alkene
(c) BLUGOLD digit B
alkene
(d) BLUGOLD digit G
alkene
4 or 5
6 or 7
8 or 9
H2SO4 /H2 O
Br2 /H 2O
IN3 /CH2Cl2
HCl
6. [5 pts. each] Complete the following reactions by drawing the structure of the final product, using the
starting compound based on your BLUGOLD nimber as specified.
ALKENES:
0 or 1
2 or 3
(a) BLUGOLD digit B
alkene
(b)BLUGOLD digit C
alkene
(c) BLUGOLD digit G
alkene
(d) BLUGOLD digit F
alkene
(e) BLUGOLD digit G
alkene
(f) BLUGOLD digit F
alkene
4 or 5
D2SO4 /D2 O
Br2 /H 2O
IN3 /CH2Cl2
DCl
1) BH3•THF
2) H2 O2/NaOH/H2O
1) Hg(OAc)2 /THF/H 2O
2) NaBH4/NaOH/H2O
6 or 7
8 or 9
7. [5 pts. each] Complete the following reactions by drawing the structure of the starting alkene or
providing the structure of the missing reagent, using the finsl compound based on your BLUGOLD
number as specified.
Br
(a)
alkene
Br2/H2 O
BLUGOLD digit B:
alkene
OH
OH
Br
Br
0-4
Me
(b)
Br
5-9
Br
DBr
BLUGOLD digit E:
0-4
Me
Me
D
Br
5-9
OH
D
D
D
(c)
OH
?
BLUGOLD digit D:
0-4
5-9
ANSWER SHEET
NAME:
BLUGOLD:
NUMBER
A
B
C
D
E
F
G
1.
0 or 1: E-4-bromo-3-methyl-3-penten-1-ol
2 or 3: Z-4-bromo-3-methyl-3-penten-1-ol
4 or 5: Z-3-bromo-4-methyl-2-penten-1-ol
6 or 7: E-4-bromo-3-methyl-2-penten-1-ol
8 or 9: Z-3-bromo-4-methyl-2-penten-1-ol
2.
3.
OH
OH
OH
OH
OH
F
F
OH
0,1
F
F
0,1
2,3
4 (a)
4,5
F
F
6,7
8,9
OH
F
2,3
OH
F
4,5
6,7
8,9
4(b)
‡2
H
Me
0-4
OH2
‡3
E
Me
5-9
OH2
Reaction Coordinate
4 (c)
H
OH
Br
OH2
H
OH
F
‡1
Br
OH
F
4 (a)
4(b)
‡1
D
‡2
0-4
‡3
D
0-4
D
E
D
5-9
Cl
5-9
D
Reaction Coordinate
4 (c)
Cl
Cl
D
5 (a)
D
D
5 (b)
OH
OH
HO
0,1
Br
2,3
0,1
Br
2,3
OH
OH
OH
HO
OH Br
Br
4,5,8
6,7,9
5 (c)
4,5,8
6,7,9
5 (d)
N3
0,1
N3
I
Cl
N3
I
2,3
Cl
2,3
0,1
Cl
Cl
N3 I
I
4,5,8
4,5,8
6,7,9
6,7,9
6 (a)
6 (b)
HO
HO
HO
D
D
0,1
HO
Br
D
2,3
4,5
OH
0,1
Br
D
Br
D
8,9
OH
4,5
OH
Br
6,7
6 (c)
OH
8,9
6 (d)
N3
I
N3
0,1
I
N3
I
4,5
2,3
C
l
Cl
Cl
D
D
0,1
N3
I
N3
4,5
Cl
I
6,7
D
2,3
Cl
D
D
6,7
8,9
6 (e)
8,9
6 (f)
HO
HO
0,1
HO
2,3
8,9
Br
Br
Me
5-9
Me
0-4
Me
0,1
H
5-9
HO
2,3
4,5
HO
HO
6,7
0-4
HO
HO
4,5
HO
HO
7 (b)
Br
HO
6,7
7. (a)
OH
2,3
6,7
8,9
7 (c)
1) BH3•THF, 2) H2O2/H2O/NaOH
or
1) Hg(OAc)2/H2O/THF, 2) NaBH4/NaOH/H2O