CHEM 363
spring 2007
Name________________________________
Take-Home Questions for Final Exam
1) (3 pts.) Provide a structure for the most stable conformation of trans-1,2dimethylcyclohexane.
2) (4 pts.) Provide a Newman projection for the product of the reaction shown
below.
(E)-2,3-diphenyl-2-butene
Br2
?
3) (6 pts.) The diazonium shown below decomposes to give an intermediate that
gives rise to each of the products shown below. Provide a mechanism for the
formation of each product from the diazonium ion. Show all steps and
intermediates. Use electron-pushing arrows to help describe those steps in
which bonds to carbon are broken or formed.
ClNH2 NaNO2
HCl, H2O
N2
OH
+
OH
+
4) (4 pts.) Provide a mechanism for the reaction shown below. Show all steps
and intermediates. Use electron-pushing arrows to help describe those steps in
which bonds to carbon are broken or formed.
H
OCH3
H3O+, H218O
H
18
O
H
+ CH3OH
5) (6 pts.) Provide structures for the following compounds, both having the
formula C8H11N, based on the spectral data given below.
a) Compound A
IR: 3400 cm-1 (sharp)
NMR:  7.2 (t, 2H), 6.8 (t, 1H), 6.7 (d, 2H), 3.6 (broad s, 1H), 3.2 (q, 2H), 1.3
(t, 3H)
1H
b) Compound B
IR: 3430, 3350 cm-1
1H
NMR:  7.0 (d, 2H), 6.7 (d, 2H), 3.6 (s, 2H), 2.6 (q, 2H), 1.2 (t, 3H)
5) (30 pts.) Show how to carry out each of the following synthetic
transformations. For fullest credit, show all necessary reagents and the product
of each synthetic step.
O
a)
b)
alcohols having
four carbons or
fewer
O
O
c)
O
OEt
H
OH
d)
O
N
HO
e)
using benzene as
the only source of
carbon
N
N
6) (8 pts.) Bombykol, the sex pheromone of the silkworm moth, has been
prepared in the following way.
a) Provide structures for compounds A-F.
b) Provide a structure for bombykol.
c) Are there any uncertainties in your answer? Explain.
Ph =
1-pentyne +
A (C5H7MgBr)
MgBr
A + H2C=O; then H+
B + PBr3
C + Ph3P, base
D + ethyl 10-oxodecanoate
E + H2, Lindlar catalyst
F + LiAlH4
B (C6H10O)
C (C6H9Br)
D (C24H23P)
E (C18H30O2)
F (C18H32O)
bombykol (C16H30O)