1

CH203 Fall 2014 Exam Three Practice Test

Answers
11/24/14
1. Which of the following compounds is the strongest acid?
a. CH3CH2CH2COOH
b. CH3CH2CHClCOOH
c. CH3CHClCH2COOH
d. ClCH2CH2CH2COOH
ANS: B
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

ANS: B
3. Which of the following compounds has the highest pKa?
a. NH3
b. H2O
c. HCl
d. CH4
ANS: D
4. Which of the following compounds has the lowest pKa?
a. H2O
b. HBr
c. NH3
d. CH4
ANS: B
5. Which of the following compounds has the lowest pKa?
a. H2O
b. H2S
c. H2Se
d. H2Te
ANS: D

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

ANS: C
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+

ANS: C
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
ANS: C
9. Which sets of curved arrows accounts for the protonation of propene with HI?

a.
b.
c.
d.

1
2
3
4

ANS: D

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

a.
b.
c.
d.

1
2
3
4

ANS: D
11. What is the value of the equilibrium constant, Keq, for the following reaction?

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

ANS: A
12. Which of the following is a Lewis acid but not a Brnsted-Lowry acid?
a. CH3COOH
b. AlCl3
c. H2O
d. CH3OH
ANS: B
13. Which of the following energy diagrams represents the slowest reaction?

a.
b.
c.
d.

1
2
3
4

ANS: D
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
ANS: C
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
ANS: A
16. Which of the following energy diagrams best represents the changes in energy during addition of
HBr to an alkene?

a.
b.
c.
d.

1
2
3
4

ANS: A

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.

ANS:

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.

ANS:

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

a.
b.
c.
d.

1
2
3
4

ANS: C

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

a.
b.
c.
d.

1
2
3
4

ANS: C
21. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: C
22. What is the major organic product obtained from the following reaction?

a. 1
b. 2
c. 3

d. 4
ANS: B
23. What is (are) the major organic product(s) obtained from the following reaction?

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

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

ANS: C
24. What is (are) the major organic product(s) obtained from the following reaction?

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

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

ANS: D
25. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: A
26. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: D
27. What is (are) the major organic product(s) obtained from the following reaction?

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

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

ANS: D

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

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

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

ANS: C
29. What is the best choice of reagent to perform the following transformation?

a.
b.
c.
d.

Br2
HBr
Br2, H2O
N-bromosuccinimide

ANS: C
30. 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
ANS: D

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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
ANS: A
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)
ANS: D
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)
ANS: B
34. What is the IUPAC name of the following compound?

a.
b.
c.
d.

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

ANS: B
35. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

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

ANS: C
36. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

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

ANS: B
37. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

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

ANS: D
38. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

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

ANS: B

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

a.
b.
c.
d.

1
2
3
4

ANS: D
40. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: D

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

a.
b.
c.
d.

1
2
3
4

ANS: A
42. What is the best choice of reagent(s) to perform the following transformation?

a.
b.
c.
d.

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

ANS: D
43. What is the best choice of reagent(s) to perform the following transformation?

a. H2/Pt
b. H2/Lindlar catalyst

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c. Na/NH3
d. BH3; followed by H2O2, NaOH
ANS: C
44. What is the major organic product obtained from the following series of reactions?

a.
b.
c.
d.

1
2
3
4

ANS: A
45. What is the major organic product obtained from the following series of reactions?

a.
b.
c.
d.

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

ANS: B

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

ANS:

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

ANS:

48.

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Predict the products:

OMe
HCl (1.0 equiv.)

Br2

Answer:
OMe
OMe
HCl (1.0 equiv.)

Cl

OMe
Br2

Br

OMe
Br

Cl

Br
Br
Cl

49.

Predict the products:

Answer:
Na or Li,
NH3 (liquid)

Me

Me

Pd, H2,

Me

H2, Lindlar Cat

Me

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50.
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.
Product I
OCH3
Cl
H
O
H
+

step I
step II
H
OCH3
HO
A

Product II
(diastereomer of product I)

Compound I

Answer:
Product I
step I

H
OCH3

Na (or Li), NH3;

or Pd, H2,
quinoline (or PbO).

step II
H

Cl2

HO

H
HO

OCH3

Cl Cl
H

OCH3 athw
p

ay

OCH3

H Cl H OH

Cl
H
H

Cl

OCH3
O
H

pa
ay

H OH

w
th

Compound I

H Cl
H

OCH3
H OH Cl

Cl
H
H

OCH3
O
+

Cl
H
H

OCH3
O

Product II
(diastereomer of product I)

Compound I

Cl
H
H

Cl
OCH3

O
H

Cl

Cl
H
H

OCH3
O

Product i

Cl
H
H

OCH3
O

Product iI

c.

H
O

b.

from alkene

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from alkene
3. (8 pts) Mechanism Addition of Br2 to cyclohexene. Be sure to indicate any relevant stereochemistry!
8. (12 pts) Retrosynthesis
SuggestBra2starting material and reagent for the reaction:
a. 51.
Na, NH 3
from alkyne
c.
H
H

from alkene

b.

CH2I 2/Zn(Cu)
3. (8 pts) Mechanism
Answer: Addition of Br2 to cyclohexene. Be sure to indicate any relevant stereochemistry!
Br 2
c.

1) O3, -78 C
2) Me 2S

from alkene

H
O

from alkene

9. (8 pts)
Mechanism
Addition
of Br2and
to cyclohexene.
to indicateofany
stereochemistry!
52.
Predict
the product
draw out the Be
fullsure
mechanism
therelevant
reaction:
Br
2
4. (8 pts) Mechanism Addition of H O to cyclohexene. Be sure to indicate any relevant stereochemistry!
2

H 2O
H 2SO 4
!+
Br

Answer:

!"
Br

Br
Br

Br

Br
4. (8 pts) Mechanism Addition of H2O to cyclohexene. Be sure to indicate any relevant stereochemistry!
trans
OH2
H 2OH
H 2SO 4

CH3

or

CH3

O
H

10. (8 pts) Mechanism Addition of H2O to cyclohexene. Be sure to indicate any relevant stereochemistry!
CH3
O
3
HCH
2O
H

H 2SO 4

OH

H
O

H
5. (5 pts) When the following cyclic ether is treated with methanol and a catalytic amount of H2SO4, one of the two
H following
OH
O one
H regioisomer with only a trace of the other. Draw
53.
The
reaction
gives mostly
products
shown2 is formed
quantitatively
with only
a trace of the other. Which one is the major product? Propose a
out
the reaction
mechanism
andwhy.
explain the formation of the product. -H +
reaction
mechanism
to illustrate
H
H
H
OCH
or
3
CH OH, H SO
3

Answer:

OCH3

O H
H

O H

O
OCH
o
products
shown
is the
formed
a trace
of the other.
is thethat
major
product?
Propose
a
3 on
O quantitatively
The product
right
is the major with
one.only
Both
carbocations
are 2Which
, but one
the one
leads
to the major
product
is
reaction
mechanism
to
illustrate
why.
resonance stabilized by the lone pairs on the ether oxygen.

OCH

3
CH3OH, H2SO 4
o
H
ght is the major one. Both carbocations are 2 , but the
one
that
leads
to the majorHproduct is
+
y the lone pairs
on
the
ether
oxygen.
O
OCH3
O
O
O
O
The first product
is the major product
formed due to the greater stability of the
H
H

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secondary
carbocation formed next to the oxygen. The oxygen atomo resonance stabilizes the cation with its
The product on the right is the major one. Both carbocations are 2 , but the one that leads to the major product is
lone pairs:
O
O
resonance stabilized by the lone pairs on the ether oxygen.

H
O

Methanol adds to that carbocation and is deprotonated by solvent to give the product.

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 theonly
following
reaction,
only one
product
is recovered.
product
is it,and
andbriefly
why?state why.
ICl to styrene
one of the
two indicated
products
is formed.
PleaseWhich
indicate
which one
ve learned that symmetrical dihalides (X2, X=Cl, Br) add to alkenes to form vicinal dihalides.
alides such as iodine monochloride (!"#) also add to alkenes. For the following addition reaction of
one of the two indicated products is formed. Please indicate which one and briefly state why.

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
Answer:
Chlorine
is more electronegative than iodine. Therefore iodine would bear the partial positive charge in the mechanism
ICl to styrene only one of the two indicated products is formed. Please indicate which one and briefly state why.
and add first. The cyclic iodonium ion would be broken by the chloride at the site that best handles positive charge the
secondary
site. electronegative
So the product on
the I,
right
Cl is more
than
so is
in preferred.
ICl the iodine has a slight positive character and is
ronegative than iodine.
iodine Lewis
would bear
partial
positive
charge inion.
the The
mechanism
attackedTherefore
by the alkene
base the
to give
a cyclic
iodonium
free chloride then adds anti
clic iodonium ion coplanar
would be to
broken
by
the
chloride
at
the
site
that
best
handles
positive
charge
the
the iodonium ion at the carbon which is more able to bear the
positive character the
product on the right is preferred.
"
+
!
secondary benzylic carbon. This gives the product
on!the right.
I Cl
I
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
I Cl
Cl
I
secondary site. So the product on the right is preferred.

Cl

!+

!"
I Cl

I
Cl

Score: ______/100

Score: ______/100

Projected Course Grade: _____

Projected Course Grade: _____

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