Chemistry 30B

Exam 2 Practice Problems

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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.

Answer each question by writing one word in each blank.

(a) In x-ray crystallography x-ray photons are _____ by regularly spaced atoms in a(n) _____.
(b) In an early but very important application of x-ray crystallography, the Braggs measured (for the
first time) carbon-carbon bond lengths and carbon-carbon-carbon bond angles in a substance called
_____.
(c) Rosalind Franklin verified that DNA is a helical molecule when she saw a(n) _____ pattern in
photo 51, one of many DNA diffraction patterns produced by x-ray crystallography.

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

Alcohols and Ethers

4.

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

Exam 2 Practice Problems

HO

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.

Write a mechanism for the formation of the major product.

CH3
O

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.

Multi-step Organic Synthesis

10. Suggest a series of reactions to carry out the following transformations. You may use any needed
reagents and reasonable reactions. Logical retrosynthesis may earn some partial credit, but is not
required. These transformations cannot be accomplished in a single step.

Chemistry 30B

Exam 2 Practice Problems

(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

(a) Circle the reaction which has an epoxide: B C Both Neither

(b) Circle the letter of the faster reaction: B C Rates about equal
(c) Write a mechanism for the faster reaction.
(d) Complete this explanation by adding no more than twenty words: This is the faster reaction
because...
13. Consider the following three reactions that all attempt to produce molecule D.

OH

NaH

Molecule D

OH

NaOH

Molecule D

Reaction E

Reaction F

(a) Write the structure of molecule D.

(b) Which is the most efficient reaction to synthesize molecule D?
(c) Provide a mechanism for this most efficient route.
(d) Very briefly explain why the other two reactions are less efficient.

NaH

Molecule D

OH

Reaction G

Chemistry 30B

Exam 2 Practice Problems

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Question 1517 refer to this general reaction scheme:

OH
Reactants

OH
+

+
OH

Product H

Product I

Product J

14. Consider the case where reactants = aqueous H2SO4.

(a) Write a mechanism that accounts for the formation of products H, I, and J.
(b)Which product is major?
15. Consider the case where reactants = (1) BH3 (2) NaOH and HOOH.
(a) What is the name of this reaction?
(b) Which product is major?
(c) Provide the complete mechanism for the BH3 step of this reaction.
(d) Is the regiochemistry best described as Markovnikov, anti-Markovnikov, or neither?
16. Consider the case where reactants = (1) Hg(CH3CO2)2/H2O (2) NaBH4.
(a) What is the name of this reaction?
(b) Which product is major?
(c) Provide the complete mechanism for the Hg(CH3CO2)2/H2O step of this reaction.
(d) Is the regiochemistry best described as Markovnikov, anti-Markovnikov, or neither?
(e) Unlike acid-catalyzed alkene hydration, this reaction never involves rearrangement of carboncarbon or carbon-hydrogen bonds. Explain.
17. Oxonium ions are mechanism intermediates in many reactions of alcohols and ethers.
(a) Define oxonium ion and give a clear example using a molecule that has exactly six carbons and
any number of atoms of other elements. Do not use any abbreviations such as R or X. Your
oxonium ion example must be able to suffer all four oxonium ion fates in part (b).
(b) In any reaction mechanism, an oxonium ion can only undergo four different mechanism fates.
Name these fates, and illustrate each using your oxonium ion example from part (a) along with any
other needed reactants. Include curved arrows and products for each illustration.
18. The reactions of alcohols with reagents such as PBr3, SOCl2 and aqueous HCl all give alkyl halides.
(a) In one sentence or less, state what is similar about the leaving group in each of these reactions.
(b) Give an example of each reaction that illustrates is stereochemistry (inversion, retention, mixture).
Include all reactants and products.
19. Complete these sentences by adding no more than four words in each case.
(a) Alkoxides are good nucleophiles because they have...
(b) Epoxides are more reactive than other ethers due to...