Problem Set 5
Chapter 6
Due: Monday, October 11, 2004
1. Study #2 and #3 in the Alkyl Halide
module and #1 in the Ether module in ORGO. 2. Achiral compound A
(C8H14) is inert toward hydrogen in
the presence of a catalyst. Compound A can and does
form two, and only two, monosubstitution products upon free
radical chlorination. One of these products, B, is
achiral while C is a racemate. Compound B is
inert toward
C2H5ONa/C2H5OH
while compound C affords achiral compound D.
a) What are the structures of A-D?
Show your reasoning. b) What is the ratio C/B in the
chlorination of A? Show work. 3. When 1-bromo-2,2-dideuteriocyclohexane
is heated in the presence of sodium ethoxide in ethanol, the
major product formed is a cyclohexene. What is its structure
and why is it formed? 4. When (2S, 3S)-2-chloro-3-methylheptane
(A) is heated in the presence of
CH3ONa/CH3OH, two alkenes B
(opt. active) and C are formed. When the (2S, 3R)
diastereomer of A is subjected to the same reaction
conditions, B' and D are formed. a) What are the structures of B,B',C
and D? b) Is B or C the major
product? c) Is B' or D the major
product? d) How do C and D
differ? e) How do B and B'
differ? f) Illustrate the mechanism for the
formation of B,B',C and D. 5. What are the structures of A in
a)-d)? Explain and provide mechanisms for each of the five
reactions. 6. Bromide B is the predicted
major product derived from A. Bromide G is one
of two conceivable structures derived from F. Bromide
B is not the other one, nor is it a minor product
from the bromination of A. Only G can be
found. What are the structures A-G? Explain and
illustrate.