1

CH203 Fall 2014 Exam Three Practice Test

11/24/14
1. Which of the following compounds is the strongest acid?
a. CH3CH2CH2COOH
b. CH3CH2CHClCOOH
c. CH3CHClCH2COOH
d. ClCH2CH2CH2COOH
2. Which of the following is the strongest base?
a. iodide anion, I
b. fluoride anion, F
c. bromide anion, Br
d. chloride anion, Cl

3. Which of the following compounds has the highest pKa?

a. NH3
b. H2O
c. HCl
d. CH4
4. Which of the following compounds has the lowest pKa?
a. H2O
b. HBr
c. NH3
d. CH4
5. Which of the following compounds has the lowest pKa?
a. H2O
b. H2S
c. H2Se
d. H2Te
6. Which of the following is present in the highest concentration upon dissolution of H2SO4 in
water?
a. H2SO4
b. H+
c. H3O+
d. HO

7. Which of the following is present in the highest concentration upon dissolution of acetic acid in
water?
a. OH
b. H3O+
c. CH3COOH
d. CH3COOH+

8.

Which of the following terms describes the reactivity of boron tribromide, BBr3?
a. Brnsted-Lowry acid and Lewis acid
b. Brnsted-Lowry base and Lewis base
c. Lewis acid and not a Brnsted-Lowry acid
d. Lewis base and not a Brnsted-Lowry base

9.

Which sets of curved arrows accounts for the protonation of propene with HI?

a.
b.
c.
d.
10.

Which species is the conjugate acid in the following acid-base reaction?

a.
b.
c.
d.
11.

1
2
3
4

1
2
3
4

What is the value of the equilibrium constant, Keq, for the following reaction?

a. 1013
b. 10 13
c. 13
d. 1/13

12.

Which of the following is a Lewis acid but not a Brnsted-Lowry acid?

a. CH3COOH

b. AlCl3
c. H2O
d. CH3OH
13.

Which of the following energy diagrams represents the slowest reaction?

a.
b.
c.
d.

1
2
3
4

14.

Which of the following is a definition of the rate-determining step of a reaction mechanism?

a. the first step
b. the last step
c. the step that crosses the highest energy barrier
d. the most exothermic step

15.

Which of the following is a definition of the activation energy of a reaction?

a. the difference in Gibbs free energy between the reactants and the transition state
b. the difference in Gibbs free energy between the reactants and the intermediate
c. the difference in Gibbs free energy between the reactants and the product
d. the difference in Gibbs free energy between the transition state and the product

16.

Which of the following energy diagrams best represents the changes in energy during addition of
HBr to an alkene?

a. 1
b. 2
c. 3

d. 4
17.

Use curved arrows to show the movement of pairs of electrons in the following acid-base
reaction and show the structures of the conjugate acid and conjugate base.

18.

Use curved arrows to show the movement of pairs of electrons in the following reaction between
a Lewis acid and a Lewis base, and show the structure of the product.

19.

What is the major organic product obtained from the following reaction?

a.
b.
c.
d.
20.

What is the major organic product obtained from the following reaction?

a.
b.
c.
d.
21.

1
2
3
4

1
2
3
4

What is the major organic product obtained from the following reaction?

a.
b.
c.
d.
22.

1
2
3
4

What is (are) the major organic product(s) obtained from the following reaction?

1.
2.
3.
a.
b.
c.
d.
24.

1
2
3
4

What is the major organic product obtained from the following reaction?

a.
b.
c.
d.
23.

(2R,3R)-dibromobutane
(2S,3S)-dibromobutane
meso-2,3-dibromobutane
only 1
only 2
only 3
only 1 and 2

What is (are) the major organic product(s) obtained from the following reaction?

1.

(2R,3R)-dibromobutane

2.
3.
a.
b.
c.
d.
25.

1
2
3
4

What is the major organic product obtained from the following reaction?

a.
b.
c.
d.
27.

only 1
only 2
only 3
only 1 and 2

What is the major organic product obtained from the following reaction?

a.
b.
c.
d.
26.

(2S,3S)-dibromobutane
meso-2,3-dibromobutane

1
2
3
4

What is (are) the major organic product(s) obtained from the following reaction?

1.
2.
3.
a.
b.
c.
d.
28.

a.
b.
c.
d.

only 1
only 2
only 3
only 1 and 2

(2R,3R)-butanediol
(2S,3S)-butanediol
meso-2,3-butanediol
only 1
only 2
only 3
only 1 and 2

What is the best choice of reagent to perform the following transformation?

a.
b.
c.
d.
30.

(2R,3R)-butanediol
(2S,3S)-butanediol
meso-2,3-butanediol

What is (are) the major organic product(s) obtained from the following reaction?

1.
2.
3.

29.

Br2
HBr
Br2, H2O
N-bromosuccinimide

What type of reactive intermediate is formed in the reaction of an alkene with Br2 and water to
give a bromohydrin?
a. carbocation
b. carbanion
c. radical
d. cyclic bromonium ion

31.

What type of reactive intermediate is formed in the reaction of an alkene with aqueous acid to
give an alcohol?
a. carbocation
b. carbanion
c. radical
d. carbene

32.

Which of the following reactions of alkenes takes place with anti stereospecificity?
a. bishydroxylation (treatment with OsO4 followed by NaHSO3)
b. hydrogenation (treatment with H2/Pt)
c. addition of HBr (treatment with HBr)
d. bromohydrin formation (treatment with Br2, H2O)

33.

Which of the following reactions of alkenes takes place with syn stereospecificity?
a. addition of bromine (treatment with Br2)
b. hydrogenation (treatment with H2/Pt)
c. addition of HBr (treatment with HBr)
d. acid-catalyzed hydration (treatment with aqueous H2SO4)

34.

What is the IUPAC name of the following compound?

a.
b.
c.
d.
35.

What is the major organic product obtained from the following reaction?

a.
b.
c.
d.
36.

(R)-4-methyl-2-hexyne
(S)-4-methyl-2-hexyne
(R)-3-methyl-4-hexyne
(S)-3-methyl-4-hexyne

(E) 2-butene
(Z) 2-butene
2-butyne
1-butyne

What is the major organic product obtained from the following reaction?

a.
b.
c.
d.
37.

3,4-dibromohexane
3,3-dibromohexane
(Z) 3,4-dibromohexene
3,3,4,4-tetrabromohexane

What is the major organic product obtained from the following reaction?

a.
b.
c.
d.
39.

2-methyl-3-hexene
2-methyl-3-heptyne
2-bromo-3-methylbutane
2-methyl-2-butene

What is the major organic product obtained from the following reaction?

a.
b.
c.
d.
38.

2-hexanone
hexanal
2-hexanol
cis-2-hexene

What is the major organic product obtained from the following reaction?

a. 1
b. 2

10

c. 3
d. 4
40.

What is the major organic product obtained from the following reaction?

a.
b.
c.
d.
41.

What is the major organic product obtained from the following reaction?

a.
b.
c.
d.
42.

1
2
3
4

1
2
3
4

What is the best choice of reagent(s) to perform the following transformation?

a.
b.
c.
d.
43.

H2/Pt
H2/Lindlar catalyst
Na/NH3
BH3; followed by H2O2, NaOH

What is the major organic product obtained from the following series of reactions?

a.
b.
c.
d.
45.

1 mol of Br2
2 mol of Br2
1 mol of HBr
2 mol of HBr

What is the best choice of reagent(s) to perform the following transformation?

a.
b.
c.
d.
44.

11

1
2
3
4

What is the major organic product obtained from the following series of reactions?

a.
b.
c.
d.

12

(Z)-2-heptene
(E)-2-heptene
1-heptene
heptane

46.

Outline how one might achieve the following transformation, showing reagents and the isolated
intermediates in the synthetic scheme.

47.

Outline how one might achieve the following transformation, showing reagents and the isolated
intermediates in the synthetic scheme.

48.

Predict the products:

OMe
HCl (1.0 equiv.)

49.

Predict the products:

Na or Li,
NH3 (liquid)
Me
Pd, H2,

H2, Lindlar Cat

Br2

2. (12 pts) Retrosynthesis

a.

13 alkyne
from

50.

b.
Provide the reaction conditions to synthesize the product from starting material A. Fill the missing
compound I and product II. Provide the reaction mechanism for step II.

c.

Product I
OCH3
Cl
H
H
OO
H
+

step I
step II

from alkene

from alkene

2. (12Hpts) Retrosynthesis
Mechanism
Addition of Br2 to cyclohexene. Be sure to indicate any relevant stereochemistry!
3
a. 3. (8 pts) OCH
Br 2
HO
from alkyne
A

Product II
Compound I
b. 11. (5 pts) When the following cyclic ether is treated with methanol(diastereomer
of product
and a catalytic
amountI)of H2SO4, one of the two
products shown is formed quantitatively with only a trace of the other. Which one is the major
product? Propose a
from alkene
reaction mechanism to illustrate why.

51.
c.

Suggest a starting material and reagent for the reaction:OCH3

CH3OH, H2SO 4

+
O

OCH3

HO

from alkene

The product on the right is the major one. Both carbocations are 2 , but the one that leads to the major product is
resonance stabilized by the lone pairs on the ether oxygen.
3. (8 pts) Mechanism Addition of Br2 to cyclohexene. Be sure to indicate any relevant stereochemistry!
Br 2the product and draw out the full mechanism of the reaction:
52. Predict
H
H
4. (8 pts) Mechanism Addition of H2O to cyclohexene. Be sure to indicate any relevant stereochemistry!
H 2O
O
O
H 2SO 4

53.

5. (5 pts) When the following cyclic ether is treated with methanol and a catalytic amount of H2SO4, one of the two
The
following
reaction
gives
mostly one
regioisomer
only
a trace
of the
the Propose a
products
shown
is formed
quantitatively
with
only a tracewith
of the
other.
Which
oneother.
is theDraw
major out
product?
reaction
and
explain
the formation of the product.
reaction mechanism
mechanism to
illustrate
why.

OCH3

CH3OH, H2SO 4

+
O

OCH3

12. (5 pts) You have learned that symmetrical dihalides (X2, X=Cl, Br) add to alkenes to form vicinal dihalides.
Unsymmetrical dihalides such as iodine monochloride (!"#) also add to alkenes. For the following addition reaction of
54.
In
following
product
is recovered.
it, and
why?
IClthe
to styrene
onlyreaction,
one of theonly
two one
indicated
products
is formed.Which
Pleaseproduct
indicateiswhich
one
and briefly state why.
4. (8 pts) Mechanism Addition of H2O to cyclohexene. Be sure to indicate any relevant stereochemistry!
H 2O

H 2SO 4

Chlorine is more electronegative than iodine. Therefore iodine would bear the partial positive charge in the mechanism
and add first. The cyclic iodonium ion would be broken by the chloride at the site that best handles positive charge the
secondary site. So the product on the right is preferred.

!+

!"