Chem 232
D. J. Wardrop
[email protected]
Problem Set 1
Question 1.
For each of the following structures, provide the empirical formula.
Question 2.
Draw full zig-zig representations for the following formulae. Name the functional groups present in each molecule.
x
Question 3.
Use valence shell electron pair repulsion (VSEPR) theory to predict the structure of the following reactive
intermediates. For a brief revision of VSEPR, see http://en.wikipedia.org/wiki/VSEPR.
XeF2
H
SF4
Me
H
Me
H
Me
Me
Question 4.
Draw the major organic product for each of the reaction schemes below. Draw a reasonable arrow-pushing
mechanism for each transformation.
Br
KOtBu
OH
b
a.
HCl
Cl
THF
Me
Br2
c
d
hν
minor
major
e
Me
f
Cl
H2SO4
H2O
hν
Cl
Me
OH
Me
OH
H2O
Br
Cl2
H2SO4
Me
OH
Question 5.
Draw the major and minor organic products for each of the reaction schemes below. Draw a reasonable arrowpushing mechanism for each transformation.
a.
H3PO4
Ph
heat
OH
Ph
OH
b
major
H3PO4
heat
minor
major
OH
c
Me
H2SO4
heat
H3PO4
d
Me
OH
Me
heat
Me
minor
Me
Question 6 (requires knowledge from Chapter 7)
Photochemical bromination of 1 (αD = +4.21) affords hydrogen bromide (3) and alkyl bromide 2, which is racemic (αD
= 0). Draw a detailed arrow-pushing mechanism for this transformation. Provide a mechanistic explanation for a) the
regioselectivity of this reaction and, b) the observed loss of optical activity
Me
H
F
Me
1
Br2
hν
Me
Br
F
Me
2
H Br
3