Name
(This is an "open brain" exam, those who brought their brain, are
encouraged to keep it open during the examination).
1) Explain in a simple sentence what is meant in a chemical sense by the
following arrows. (7.5 pts)
(a)
(b)
(c)
(d)
(e)
O-H
O
O-R
R-C C-R
R O-H
R O-R
O
R
R
O
H
O
Cl
R NH2
(a)
H3C
(b)
(c)
H3C
Br
H
H
H Br
H3C
H3C
CH3
CH3
Br H
(d)
H Br
H3C
H3C
CH3
Br H
(e) Ph C C:-
H
CH3
Ph C C CH3
+ CH3-Br
4) Draw Lewis structures (sticks for bonds, and dots for lone pairs) for the
below two molecules. (6.5pts)
CH3CH2OH
CH3CO2H
5) For the above two molecules, label the hybridization of all the carbons
and oxygens. (5pts)
6) Explain why ethanoic acid is a much stronger acid than ethanol. (10pts)
7) On the below energy level diagram, label (a) the axes (b) the reactants
and products (c) any transitions states (d) Ho for the overall reaction (e)
is this reaction exothermic or endothermic (f) is this reaction more likely
to proceed by an E1 or E2 mechanism? (10pts)
9) Briefly explain which of the two above geometries best describes CH3
(methyl radical)? (3pts)
10)
(b)
(c)
(d)
F
OH
(e)
Br
11) Asterix any chiral atoms in these molecules, and assign R or S to each
chiral center. (15pts)
H
(a)
(b)
Cl
F
CH3
F
F
F
F
F
F
F
F
CH3
CF3
(c)
(d)
H
H
CH2F
Cl
Cl
CH2F
12) Which of the above molecules are achiral, and in a sentence explain
why they are achiral. (4pts)
13) Circle the more stable member of each pair, and in a sentence explain
your choice. (15pts)
+
(a)
(b)
CH2
(c)
CH2
(d)
+
CH2
(e)
15) Name the two different positions that the hydrogens of cyclohexane
can be located in the more stable geometrical conformation. (2pts)
17) Name the two allowed geometries for any elimination reaction to
proceed. (3pts)
H
C
CH3OH
CH2-Br
SN1
D2C
H
C
C
H2
OCH3
H2C
H
C
C
D2
OCH3
20) What would you expect the approximate ratio of these products to be?
(2pts)
21)
(a)
H3C
(d)
(e)
(f)
2) CH3CH2Br
1) Mg, Ether
(b)
(c)
1) NaNH2
H3C
2) D2O
HBr, Peroxides
CH3
1) BH3.THF
CH3
2) H2O2, NaOH
CH3
1) Hg(OAc)2,H2O
CH3
2) NaBH4
H3C
1) Na, NH3
21b) Write the mechanism for one of the above anti-Markovnikov additions.
(6pts)
22)
(a)
OH
O
(b)
(c)
O
O C CH3
OH O
O
H3C
(d)
NH2
OH
H OH
(e)
Cl H
Br
(f)
H3C
H
Br
22b) Write the mechanism for either of the above alkyne reactions. (6pts)