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These questions are drawn from old Chem 30B exams. This question list is longer than the real exam
will be. The absence of any topic among these questions should not be taken to mean that topic would
not be on the exam.
Solutions to these problems will be posted on the course web site a few days before the exam.
The Thinkbook and course textbook are good sources of additional exam practice material.
X-ray Crystallography
1.
2.
Write yes or no as appropriate if each fact about the structure of molecule A can be supported or
verified by x-ray crystallography: (a) Molecular formula; (b) Stereochemistry of the carbon bearing the
CH2SH portion; (c) Distance between the carboxylic acid carbon and the thiol sulfur atom; and (d)
Planarity of the amides.
O
N
O
Molecule A
3.
Nitrobenzene
Which of the following features of nitrobenzene can be verified or supported by x-ray crystallography?
Select one or more.
(a) Benzene ring planarity
(d) Presence of lone pairs on oxygen in nitro group
(b) Nitro group (NO2) resonance
(e) Electronegativity of oxygen > nitrogen
(c) Oxygen-nitrogen bond length
(f) Positive formal charge on nitrogen in nitro group
Write the organic product(s) of the following reactions. If more than one organic product is formed,
indicate which product is major. If no reaction occurs, write NR. Do not include any mechanism
details.
OH
(a)
(c)
Na2Cr2O7
aq. H2SO4
OH acetone
OH
NaH
(b)
(d)
CH3CO3H
OH 1. BH
3
2. NaOH, HOOH
Chemistry 30B
aq. HI
(e)
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HO
(f)
PCC
OH
OH
(g)
Ph
CrO3
HO
aq. H2SO4
acetone
OH
(i)
TsCl
OH
pyridine
C15H22O4S
OCH3
(h)
aq. HI
HO
NaSCH3
acetone
5.
Write reactions that illustrate three very different ways of adding water across the alkene group of
styrene (PhCH=CH2). Use different reagents each time.
6.
Provide a complete mechanism for this ether cleavage reaction. Your mechanism must include two
different oxonium ion fates (not two illustrations of the same fate with different oxonium ions).
aq. HI
7.
+ CH3CH2I
Provide mechanisms.
O
(a)
H2SO4
OH
H2O
OH
H2O
(b)
H2SO4
HO
OCH3
(c)
1. NaOCH3
2. CH3I
CH3O
8.
OCH3
H2SO4
CH3
CH3OH
OH
9.
CH3
or
OCH3
OH
Describe (in one sentence or less) or give a clear example for each term: (a) Alkoxide; (b) Williamson
ether synthesis; (c) Oxonium ion, and (d) PCC.
Chemistry 30B
(a)
into
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CH3O
HO
(b)
into
OCH3
OCH3
Br
11. The conversion of an alcohol into a toluenesulfonate is a useful strategy to convert an alcohol into a
wide range of other functional groups.
(a) Write the names and chemical structures of the reactants that convert CH3OH into CH3OTs.
(b) Write the complete structure for CH3OTs (no abbreviations).
(c) Finish this statement by adding no more than twenty words: -OTs is a very good leaving group
because...
(d) Illustrate the utility of CH3OTs by writing its reaction with a strong nucleophile of your choice.
Include all reactants and products as well as the mechanism.
12. Consider reactions B and C:
O
H2O
Ph
OH
H2SO4
O
OH
Ph
OH
H2SO4
H2O
Ph
Reaction B
OH
Ph
Reaction C
OH
NaH
Molecule D
OH
NaOH
Molecule D
Reaction E
Reaction F
NaH
Molecule D
OH
Reaction G
Chemistry 30B
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OH
+
+
OH
Product H
Product I
Product J