Chemistry 321
50-Minute Examination #1
Wednesday, March 27, 2003
VERSION A.
Write your answers in the space provided on the Answer Sheet provided. Keep this examination;
turn in only the Answer Sheet.
1. Name the following two compounds [8 pts]. Where it is important, points are explicitly
allocated for stereochemistry.
H
Br
Br
(a)
H
trans-1,4dibromocyclohexane
or
E-1,4-dibromocyclohexane
(b)
E-4-ethyl-3-methyl-3decene
2. Draw the structures of the following two compounds [8 pts].
(a) cis-1-bromo-2,2-dimethyl-4-octene.
(b) E-1,3-diethylcyclobutane.
(a)
(b)
H
H
Br
3. Draw the following compound in the lowest-energy chair conformation and name it [6 pts].
H3C
(a)
(b)
E-1-tert-butyl-4-methylcyclohexane
4. Draw the structure of the major organic product of each of the following reactions. Where
stereochemistry is important, points have been allotted explicitly to it [4 pts each; 40 pts].
(a)
H2SO4 /H2 O
OH
(f)
1) BH3•THF
2) H2 O2/NaOH/H2O
OH
HCl
Br
(b)
Br2/CCl 4
(g)
Br
Cl
OH
H2SO4 /H2 O
(c)
Br
HO
OH
I
IN3 /CCl4
(d)
Br2/H2O
(h)
(i)
HOBr
N3
Br
1) Hg(OCOCH3) 2/THF/H2O
Cl2/H2O
2) NaBH4/NaOH/H2 O
(e)
(j)
HO
OH
Cl
5. (a) Draw a fully-labeled reaction potential energy profile (reaction coordinate diagram) for the
following reaction, which proceeds via the intermediates shown [8 pts]. Your diagram should
show the location and relative energy of every transition state and intermediate.
Cl
slow
fast
D
fast
D
D
‡1
‡2
‡3
Energy
D
Cl
D
D
Reaction Coordinate
Note how the first transition state is the highest energy, not the lowest.
(b) Draw the mechanism of the reaction in question 5(a) by using the appropriate curly arrows
and reagents [6 pts]
Cl
Cl
slow
fast
fast
D
D
D
D
6. In each of the following reactions, either the starting compound or the reagent is missing.
Complete each reaction by supplying the missing information [4 pts each; 24 pts]
(a)
Br2 /H 2O
(d)
Br
OH
OH
OH
Br2/CCl 4
Br
Br
1) Hg(OAc)2/THF/H2O
(b)
2) NaBH4/NaOH/H2 O
1) Hg(OAc)2/THF/H2O
(e)
2) NaBH4/NaOH/H2 O
OH
OH
Br
(c)
Br2/H2O
(f)
OH
H2O
H 2SO4
OH
CHEMISTRY 321
50-MINUTE EXAMINATION #2 — Version A
WEDNESDAY, MARCH 27, 2003
NAME (Print!):
1 (a)
1 (b)
2 (a)
3. structure
2 (b)
name
4 (a)
4 (f)
4 (b)
4 (g)
4 (c)
4 (h)
4 (d)
4 (i)
4 (e)
4 (j)
5 (a)
5 (b)
Cl
D
D
6 (a)
6 (d)
6 (b)
6 (e)
6 (c)
6 (f)
D