Practice Exam I

CHEM 2322

1.

2.

3.

In an addition reaction to an alkene, the bond plays the role of:

A)

nucleophile

B)

electrophile

C)

leaving group

D)

A and B

E)

B and C

Which statement best describes the temperature dependence of an addition reaction?

A)

Addition reactions are thermodynamically favored at all temperatures.

B)

Addition reactions are thermodynamically disfavored at all temperatures.

C)

Addition reactions are thermodynamically favored at low temperatures.

D)

Addition reactions are thermodynamically favored at high temperatures.

E)

Addition reactions are thermodynamically impossible.

Which of the structures shown depicts the most stable carbocation intermediate formed in
the hydrohalogenation reaction shown?

A)

B)

II

C)

III

4.

D)

IV

E)

Which of the given reaction schemes would produce the molecule shown below?

A)

B)

C)

5.

6.

D)

Both A and B

E)

Both B and C

What would be the optimal conditions to effect the following transformation?

A)

Dilute H2SO4

B)

Concentrated H2SO4

C)

Dilute HBr

D)

Concentrated HBr

What is the expected major product for the following reaction?

A)

B)

C)

D)

E)

7.

8.

What is the name of the product formed when 5-chloro-1-methylcyclohexene is reduced

with a Pt catalyst and H2?
A)

1-chloro-2-methylcyclohexane

B)

1-chloro-3-methylcyclohexane

C)

1-chloro-5-methylcyclohexane

D)

3-chloro-1-methylcyclohexane

E)

None of the above

Which reaction intermediate is formed when 4-methylcyclohexene reacts with Br2

dissolved in CCl4?

A)

B)

II

C)

III

D)

IV

E)

9.

10.

What is the expected major product for the following reaction?

A)

B)

II

C)

III

D)

IV

E)

What are the major products for the following reaction sequence?

A)

I and II

B)

II and III

C)

III and IV

D)

I and III

E)

II and IV

11.

12.

Which of the following alkene addition reactions occur(s) specifically in syn fashion?
A)

dihydroxylation using OsO4, H2O2

B)

addition of H2

C)
D)
E)

hydroboration
addition of HCl
A, B, and C

Provide the expected major organic product of the reaction sequence shown.

A)
B)
C)
D)
E)
13.

14.

I and II
IV and V
I only
II only
III only

Which reaction is not stereospecific?

A)

B)

II

C)

III

D)

IV

For the reaction sequence shown, what is the expected major product?

15.

16.

A)

B)

II

C)

III

D)

IV

E)

What is the IUPAC name for the molecule shown below?

A)

6-bromo-3-octyne

B)

6-bromo-6-methyl-3-heptyne

C)

2-bromo-2-methyl-4-heptyne

D)

6-bromo-6,6-dimethyl-3-hexyne

E)

2-bromo-4-octyne

Which of the following is a structure for hepta-3,6-dien-1-yne?

II

17.

18.

A)

B)

II

C)

III

D)

IV

E)

Ans:

III

IV

Rank the following carbanions in order of increasing base strength.

A)

I < II < III

B)

II < III < I

C)

III < II < I

D)

III < I < II

E)

II < I < III

Select the best explanation for why methanol, CH3OH, cannot be used as a solvent for the
deprotonation of a terminal alkyne by sodium amide, NaNH2.
A)

Sodium amide is not a strong enough base to deprotonate the alkyne.

B)

Sodium amide in methanol reduces alkynes to alkenes.

C)

Methanol is a poor solvent for dissolving alkynes.

D)

Methanol is more acidic than the alkyne and will be deprotonated instead.

E)

Methanol is toxic, and should be avoided when possible.

19 . For the transformation shown below, select the expected major product.

20.

21.

A)

B)

II

C)

III

D)

IV

E)

For the reaction shown, select the expected major organic product.

A)

B)

II

C)

III

D)

IV

E)

Select the best reagent to convert 3-heptyne to trans-3-heptene?

22.

23.

24.

A)

Na/NH3

B)

1 eq. NaNH2, NH3

C)

xs NaNH2, NH3

D)

H2/Pt

E)

H2/Lindlar's catalyst

Which reagents shown below would be expected to convert 2-pentyne to (Z)-2-pentene?

A)

H2, Pt

B)

Na, NH3

C)

H2, Lindlar's catalyst

D)

excess HCl

E)

HgSO4, H2O

Which of the compounds shown below would be the most likely product expected from the
reaction scheme shown?

A)

B)

II

C)

III

D)

IV

E)

For the transformation shown, select the most appropriate reagent(s) to effect the change.

25.

26.

27.

A)

H2SO4, HgSO4, H2O

B)

1. Disiamylborane, 2. HO, H2O2

C)

K2Cr2O7, H+

D)

NaOCl

E)

H2, Pd

For the reaction shown, which of the compounds listed would be the expected major, and
final, organic product?

A)

B)

II

C)

III

D)

IV

E)

In an acid-catalyzed hydration, which of the following alkynes is expected to produce a

single ketone?
A)

2-decyne

B)

3-decyne

C)

4-decyne

D)

5-decyne

E)

All of the above will give a single product

Predict the major organic products of the reaction below.

A)
B)
C)
D)
E)
28.

What is the expected major product of the reaction sequence shown below?

A)
B)
C)
D)
E)

29.
B

I and II
II and III
I and IV
II and III
1 and III

I
II
III
IV
V

Which of the following is the most stable radical?

30.

In the molecule shown below, determine which of the highlighted C-H bonds (from a to
e) is expected to have the lowest bond dissociation energy.

A) C-Ha
B) C-Hb
C) C-Hc
D) C-Hd
E) C-He
31.

Which term most accurately describes the process shown below?

Br

A)
B)
C)
D)
E)

32.

H Br

coupling
proton transfer
halogen abstraction
hydrogen abstraction
homolytic cleavage

Which of the following is an example of termination?

33.

Which of the following is most reactive towards chlorination?

A) methane
B) chloromethane
C) dichloromethane
D) chloroform
E) ethane