Question #1Rank the following alkenes in order of MOST to LEAS.docx

Question #1
Rank the following alkenes in order of MOST to LEAST
exothermic upon catalytic hydrogenation of each to its
corresponding alkane.
N
C
4
H
9
C
4
H
9
C
4
H
9
(
C
H
2
)
1
5
C
H
3
B
r
v
s

.
N
H
4
C
l
Provide a brief explanation that describes why the reactions are
ordered as observed. What is the major stabilizing effect that
determines the stability order in this series? HINT: you’ll
likely want to draw the structure of each before you proceed.
(a) cis-2-hexene
(b) 1-hexene
(c) 2,3-dimethyl-2-butene
(d) 2-methyl-2-pentene
(e) trans-2-hexene
e
n
e
r
g
y
(
a
)
(
b
)

(
c
)
(
d
)
(
e
)
r
e
l
a
t
i
v
e
e
n
e
g
y
o
f
p
r
o
d
u
c
t
Question #2

The following sets of question pertain to intermolecular forces:
(a) Provide a valid structure for each of the following molecules
and then, arrange the compounds in order of increasing boiling
point (you may want to consult the Aldrich catalog, an MSDS,
or go to chemfinder.com to find the bps). Briefly explain your
ordering being sure to indicate the type and relative magnitude
of intermolecular interactions (e.g. VDW interactions, dipole-
dipole, and hydrogen bonding) that exist in each case.
1. dichloroethanoic acid (dichloroacetic acid)
2. 2-methoxybutane
3. ethyl 3-oxobutanoate (ethylacetoacetate)
4. n-heptane
5. 3,3-dimethyl-2-pentanol
6. 3-amino-1,2-propanediol
7. ethene (ethylene)
(b)
A
l
k
e
n
e
A
l
k
a
n
e
+

H
E
A
T
H
2
P
d
-
C
Predict which of the following salts is likely to have unusually
high solubility in a (non-aqueous) hydrocarbon solvent. Briefly
explain your choice.
(c) Normally, the drug shown below is much more soluble in
lipid-like solvents (e.g. benzene) than it is in water. However,
its water solubility INCREASES considerably when the aqueous
solution contains moderate amounts of strong acid (e.g. in the
stomach) as shown by the reaction below. Explain the
solubility differences.
N
C
4
H
9
C
4
H
9
C
4
H

9
(
C
H
2
)
1
5
C
H
3
B
r
v
s
.
N
H
4
C
l
Question #3
The following compound was recently reported in the Journal of
Medicinal Chemistry as a key synthetic intermediate in the
synthesis of a potent plant-derived natural product used in the
treatment of cancer.
H
O
H
P
h
O

C
H
3
C
H
3
H
H
Conformational Interaction
1,3-diaxial (OH and H)
1.3
1,3-diaxial (OCH3 and H)
1.7
1,3-diaxial (CH3 and t-butyl)
3.8
1,3-diaxial (OCH3 and CH3)
2.3
1,3-diaxial (OCH3 and OH)
2.4
1,3-diaxial (Ph and H)
1.9
1,3-diaxial (Ph and t-butyl)
4.1
1,3-diaxial (Ph and CH3)
3.2
1,3-diaxial (Ph and OH)
3.5
1,3-diaxial (H and C(CH3)3)
2.7
1,3-diaxial (H and CH3)
0.9
Gauche (t-butyl and OH)
2.7
Gauche (t-butyl and CH3)

2.3
Gauche (OH and CH3)
1.8
(a) Name the structure shown above WITH assignment of R/S
configuration for each stereogenic atom.
(b) Draw the two chair conformations (using the templates
provided) of the structure above. Be sure to LIST all
destabilizing interactions and provide a value for total potential
energy (E) for each conformation (more stable and less stable).
m
o
r
e
s
t
a
b
l
e
l
e
s
s
s
t
a
b
l
e
E

=
E
=
possible conformations and use this value to determine the
equilibrium constant (Keq) at 25oC for the chair flip from the
MORE stable to the LESS stable conformation. Do your values
Question #4
O
+
H
O
H
H
s
o
l
u
b
l
e
i
n
b
e
n
z
e
n

e
O
H
+
H
2
O
For the following pairs of molecules, assign the absolute
configuration (R or S) to each stereogenic carbon and indicate
the stereochemical relationship (identical, enantiomers,
diastereomers, constitutional isomers, or meso compound)
between the two molecules in each pair.
Question #5
Mirror Images Pharmaceutical Corporation has designed a novel
neuromuscular blocking agent and wants to submit the molecule
shown below for patent approval. You are the lead organic
chemist on the legal team and have been asked to investigate
certain aspects of stereochemistry in order to submit a report
along with the patent application. Your report requires the
following information:
H
3
C
H
H
C
H
3

H
H
H
3
C
C
l
C
H
3
H
O
C
H
3
O
H
H
H
O
H
C
H
3
B
r
H
3
C
O
O
C
H
3
B
r

O
H
B
r
H
3
C
B
r
H
3
C
C
l
O
H
H
O
P
a
i
r
#
1
P
a
i
r
#
2
P
a
i
r

#
3
P
a
i
r
#
4
P
a
i
r
#
5
(a) Identify all stereocenters that are not asymmetric carbons in
the molecule on the RIGHT--- label with an SC
(b) Identify all asymmetric carbons in the molecule on the
LEFT--- label with an AC
(c) Assign the configuration about all stereocenters and
asymmetric carbons on BOTH molecules --- use E/Z or R/S
assignments
(d) Provide the complete IUPAC name for the compound on the
LEFT --- identify the longest chain and any priority groups
(e) Show all polar covalent bonds by writing in the dipole arrow
for the molecule on the RIGHT
(f) Identify the stereochemical relationship between the two
molecules (identical, enantiomers, diastereomers, constitutional
isomers, or meso)

� EMBED ChemDraw.Document.4.5 ��
O
C
H
3
O
C
H
3
C
H
3
B
r
B
r
C
H
3
H

O
O
H
H
H
H
3
C
H
H
C
H
3
H
H
H
3
C
C
l
C
H
3
H
O
C
H
3
O
H
H
H
O
H
C
H

3
B
r
H
3
C
O
O
C
H
3
B
r
O
H
B
r
H
3
C
B
r
H
3
C
C
l
O
H
H
O
P
a
i
r

#
1
P
a
i
r
#
2
P
a
i
r
#
3
P
a
i
r
#
4
P
a
i
r
#
5
O
C
H
3
O
C

H
3
C
H
3
B
r
B
r
C
H
3
H
O
O
H
H
H
O
+
H
O
H
H
s
o
l
u
b
l
e
i
n
b

e
n
z
e
n
e
O
H
+
H
2
O
_1283239576.cdx
_1283239605.cdx
_1283239698.cdx
_1283240016.cdx
_1283239465.cdx
_1252479311.cdx
_1097047168.cdx
_1069486871.cdx
Due Tuesday October 25
For its validity, all hypothesis testing depends heavily on the
assumption that the sample was drawn using probability
sampling techniques. For this discussion, answer the following:
· Why is it important that a sample be random?
· What can you do if you cannot use a probability sampling
technique? (For example, suppose there is no good sampling

frame available for the population of interest.)
Provide an example of a population and explain how you would
collect a random sample from that population.

Question #1Rank the following alkenes in order of MOST to LEAS.docx

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