CH2420,

C
, Organicc Chemisstry II, Exam 1
2:003:000 PM, Februaary 8th, 20100 (total 200 points)
p

ur name CL
LEARLY heere:
Pleaase print you
Last,

TEST
T FORM

First

Makke sure you have

h
chosen the form of test that is different
d
from
m those chossen by the stuudents next to you; theree
are three forms, A, B and C,, which are printed
p
on paapers with diifferent coloors. The quesstions are thee same but
they and the answ
wers to them
m are arrangeed in differennt orders.
The exam has tw
wo parts. Parrt one containns 20 multipple choice quuestions. Thee total pointss for this parrt are 120 (6
Y need to mark
m
your annswers of theese questionns with a
200). Each quesstion has onlly one correcct answer. You
penccil on your annswer sheet.. This part will
w be gradedd using a scaanner. As a result,
r
answeers marked on
o the exam
will NOT be graaded. In addiition to answ
wers, please also
a fill the following
f
infformation onn your answer sheet: 1.
yourr name; 2. I. D. number, print it in thhe form and then
t
mark thhe corresponnding numbeers; 3. Test foorm number,
whicch is A forr you.
The second part of the exam
m contains 6 questions
q
thaat need shortt written ansswers. The tootal points foor this part
are 80.
8 Answers to these queestions need to be put in the space prrovided in thhe exam. Thiis part will be
b graded
manuually.
The total points your earned will be enteered into WeebCT. The annswer sheet for the multiple choice questions
q
may not be returrned to you. The whole exams
e
will be
b placed in front
f
of the organic
o
lab on
o the 6th flooor of
Chem
mistry Buildding after thee points are entered
e
into WebCT. Thhe keys will be
b posted in WebCT. I will
w send an
emaiil to the class when read
dy. The exam
ms that are noot picked up will remainn in my office for severall weeks and
will then be desttroyed.

Part 1: Multiple choice questions.

1. Arrange the following compounds in order of decreasing chemical shift for the underlined hydrogens
(largest value first, smallest value last).
a) CH3OCH2CH3; b) CH3CH2CH3; c) Cl2CHCH2CH3; d) ClCH2CH2CH3
A)
B)
C)
D)

b>c>a>d
c>b>a>d
a>c>d>b
c>b>d>a

2. How many nonequivalent protons does the following structure have?

A)
B)
C)
D)

12
6
4
8

3. How many signals are expected in a 13C NMR spectrum of methylcyclohexane?

A)
B)
C)
D)

4
5
6
7

4. Give the number of lines in the coupling pattern for each type of hydrogen.

A)
B)
C)
D)

a =2, b=8,c=8, d=2

a=2, b=8, c=2, d=1
a=2, b=7, c=7, d=2
a=2, b=7, c=1, d=1

5. The 1H NMR spectrum of a compound is shown below. What is the structure of the compound?

A)
O

B)
O

C)
O

D)
O

6. Rank the following alkyl radicals in order of increasing stability (least < < <most).
Ph

A)
B)
C)
D)

4<2<1<3
3<1<2<4
1<3<4<2
2<4<3<1

7. What is the major product of the following reaction?

A)
Br

B)
Br
Br

C)
Br

D)
Br

8. Consider the reaction of 2-methylpropane with a halogen. With which halogen will the product be
almost exclusively 2-halo-2-methylpropane?
A)
B)
C)
D)

F2
Cl2
Br2
I2

9. Which of the following elementary reactions corresponds to a propagation step in the formation of
chloroethane from ethane and chlorine?
CH3CH3 +

CH2CH2Cl

Cl2

HCl

A)
CH3CH2 + CH3CH3

CH3CH3 + CH3CH2

B)
hv
Cl2

2 Cl

C)
CH3CH2 +

Cl

CH3CH2Cl

D)
CH3CH2 + Cl2

CH3CH2Cl

+ Cl

10. Identify the reagent(s) that will promote the following transformation.

A)
B)
C)
D)

HBr, tetrahydrofuran
HBr, peroxides
Br2, CCl4
Br2, H2O

11. Which of the following is the MOST stable carbocation?

A)

B)

C)

D)

12. Which of the following resonance structures contributes the most to the resonance hybrid?
A)
OMe

B)
OMe

C)
OMe

D)
OMe

13. Which of the following statements regarding 1,2- or 1,4-conjugate addition of HBr to 1,3-butadiene is
FALSE?
A)
B)
C)
D)

The kinetic product, 3-bromo-1-butene, arises from the more stable carbocation intermediate.
The thermodynamic product, 1-bromo-2-butene, is the more stable product.
The kinetic product is favored by carrying out the reaction at high temperature.
Formation of the two products arises from a common resonance stabilized carbocation intermediate.

14. What is the major product of the following reaction?

A)
CHO

CHO

B)
CHO

CHO

C)
CHO

CHO

D)
CHO

CHO

15. What are the reactants needed to accomplish the following reaction?

A)
+

B)
O
+

C)

+
O

D)
O
+

16. Which of the following compounds are aromatic?

A)
B)
C)
D)

a, b, c, and d
a, c, and d
a, b, d, and e
a, b, and d

17. How many uncharged resonance structures are there for azulene?

A)
B)
C)
D)

1
2
3
4

18. Rank the following compounds in the order of increasing max

A)
B)
C)
D)

c, a, b, d
b, c, d, a
d, b, a, c
a, c, b, d

19. Which of the following alkyl halides can be prepared in good yield by radical halogenation of an
alkane?
Cl

Br
b

A)
B)
C)
D)

Cl
c

Br
d

a
b
c
d

20. Which compounds give a 1H NMR spectrum with two signals in a ratio of 2:3?
a. CH3CH2Cl; b. CH3CH2CH3; c. CH3CH2OCH2CH3; d. CH3OCH2CH2OCH3
A)
B)
C)
D)

a, c, d only
a, b only
a, c only
c, d only

10

Part 2: Questions that need short answers:

1. Draw five resonance structures for cyclopentadienyl cation. Please use appropriate curved arrows to
convert the first one to second one and so forth. (10 points. Missing or incorrectly drawing each
resonance structure will reduce 2 points, missing or incorrectly drawing each arrow will reduce 1 point
until 0 point is reached)

Other reasonable versions may also be correct

Pushing electrons two or more times to get the next resonance forms
are also OK as long as 5 resonance forms are drawn. However, the
arrows must be appropriate.

11

2. Draw a stepwise mechanism for the following reaction. Make sure to use appropriate curved arrows to
indicate movement of all electrons that moved during the reaction. Indicate how each of the products is
formed. (15 points. Missing or incorrectly drawing each structure including that of small molecules will
reduce 2 points, missing or incorrectly drawing each arrow will reduce 1 point until 0 point is reached.
The arrows for converting one resonance form to another one may be omitted)
D

1) NaH
+

2) H2O
D

omitting the sodium cation is OK

Na

O
H

D
D

with two dots here is OK

H
D

H
D

H
omitting this H is OK
D
+
HO
NaOH may be omitted here
NaOH is also good

12

3. Draw products of the following two Diels Alder reactions. Please use appropriate curved arrows to
indicate the movement of all electrons that moved during the reaction. (20 points. Missing or incorrectly
drawing a structure will reduce 8 points, missing or incorrectly drawing each arrow will reduce 3 points
until 0 point is reached)
MeO

O
Heat

OMe

MeO

O
OMe

OMe

OMe

OMe
Heat

O
OMe

O
OMe

omitting re-draw the starting material and drawing the arrows on the orignial one is also OK

If stereochemistry of the product is given, it is even better. But this is not required for the test

13

4. Write a mechanism for the reaction of CH4 with Br2 to form CH3Br and HBr under photo conditions.
Use appropriate curved arrows to indicate the movement of all electrons. (15 points. Missing or
incorrectly drawing a structure will reduce 2 points, missing or incorrectly drawing an arrow will reduce
1 point until 0 point is reached)
omitting this will reduce 2 points

Initiation
hv
Br

Br

Br

All arrows should be single-headed instead of double headed

Propagation
H
C

Br

H
Br

HBr

Br

Br

Br

Br

Termination

Br

Br

H
H

Br2

H
H

C
H

H
+

Br

Br

Drawing electrons aroung Br is OK. Omitting the words such as initiation is OK

14

5. Ethers are oxidized with O2 to form hydroperoxides that decompose violently when heated. Draw a
stepwise mechanism for this reaction. Make sure to use appropriate curved arrows to indicate the
movement of all electrons that moved during the reaction. (10 points. Missing or incorrectly drawing
each structure including that of small molecules will reduce 2 points, missing or incorrectly drawing
each arrow will reduce 1 point until 0 point is reached)

O2

OOH

OH

All arrows should be single-headed instead of double headed

OH

O
Omitting lone pairs on oxygen is OK
Omitting any upaired electrons will be considered wrong
H
O

+
O

OH

15

6. Devise a synthesis of compound B from compound A. You may use any other required organic or
inorganic reagents. Major reagents and conditions should be provided. You do not need to provide
mechanism however. (10 points. Missing or incorrectly drawing a structure including that of small
molecules that are required for the transformations will reduce 2 points until 0 point is reached)
OH

Br2

KOC(CH3)3

H2O

Br
hv

OH

H2SO4

Using thermo conditions for halogenation is OK

Using other strong base for elimination is OK
Uisng other strong acid for hydration is OK
Drawing the minor elimination product instead of the major one will not reduce points

16

CH2420,
C
, Organicc Chemisstry II, Exam 2
2:003:000 PM, Marchh 17th, 2010 (total 200 points)

ur name CL
LEARLY heere:
Pleaase print you
Last,

TEST
T FORM

First

Makke sure you have

h
chosen the form of test that is different
d
from
m those chossen by the stuudents next to you; theree
are three forms, A, B and C,, which are printed
p
on paapers with diifferent coloors. The quesstions are thee same but
they and the answ
wers to them
m are arrangeed in differennt orders.
The exam has tw
wo parts. Parrt one containns 15 multipple choice quuestions. Thee total pointss for this parrt are 120 (8
Y need to mark
m
your annswers of theese questionns with a
15). Each quesstion has onlly one correcct answer. You
penccil on your annswer sheet.. This part will
w be gradedd using a scaanner. As a result,
r
answeers marked on
o the exam
will NOT be graaded. In addiition to answ
wers, please also
a fill the following
f
infformation onn your answer sheet: 1.
yourr name; 2. I. D. number, print it in thhe form and then
t
mark thhe corresponnding numbeers; 3. Test foorm number,
whicch is A forr you.
The second part of the exam
m contains 3 questions
q
thaat need shortt written ansswers. The tootal points foor this part
are 80.
8 Answers to these queestions need to be put in the space prrovided in thhe exam. Thiis part will be
b graded
manuually.
The total points your earned will be enteered into WeebCT. The annswer sheet for the multiple choice questions
q
may not be returrned to you. Your entire exam will be placed in front
f
of the organic
o
lab on
o the 6th flooor of
Chem
mistry Buildding after thee points are entered
e
into WebCT. Thhe keys will be
b posted in ARIS. I willl send an
emaiil to the class when read
dy. The exam
ms that are noot picked up will remainn in my office for severall weeks and
will then be desttroyed.

Part 1: Multiple choice questions.

1. Which of the following is the MOST stable radical?
A.
B.
C.
D.

A methyl radical
A primary radical
A secondary radical
A tertiary radical

2. In comparing kinetic control to thermodynamic control for the reaction of butadiene and HCl, which of
the following statements represents kinetic control?
A.
B.
C.
D.

The intermediate is more stable and the product is more stable.

The intermediate is less stable and the product is more stable.
The intermediate is more stable and the product is less stable.
The intermediate is less stable and the product is less stable.

3. The 1H NMR spectrum of a compound is shown below. What is the structure of the compound?

A)
O

B)
O

C)
2

D)
O

4. The name of the following compound is

H3C

CH3

A.
B.
C.
D.

o-xylene.
m-xylene.
p-xylene.
sp-xylene.

5. The best sequence to use to form propylbenzene from benzene is

A.
B.
C.
D.

FriedelCrafts alkylation using 1-chloropropane and aluminum trichloride.

FriedelCrafts acylation followed by reduction.
Electrophilic addition of 1-chloropropane.
Nucleophilic aromatic substitution using propyl Grignard.

6. What is the electrophile in the electrophilic substitution reaction of benzene using HNO3 and H2SO4?
A.
B.
C.
D.

SO3
NO3
NO2+
NO+

7. Predict the major product of the following reaction.

CHO
HNO3
H2SO4

A. o-nitrobenzaldehyde and p-nitrobenzaldehyde

3

B. m-nitrobenzaldehyde
C. o-formylbenzenesulfonic acid and p-formylbenzenesulfonic acid
D. m-formylbenzenesulfonic acid

8. Rank the following compounds in order of increasing reactivity in electrophilic aromatic substitution
Cl

A.
B.
C.
D.

OCH3

X<Y<Z
Z<Y<X
Y<X<Z
X<Z<Y

9. Which of the following compounds is the most acidic?

CH3COOH; H2SO4; CH3OH; HF
A.
B.
C.
D.

CH3COOH
H2SO4
CH3OH
HF

10. Which of the following compounds does NOT give benzoic acid when heated with alkaline potassium
permanganate?
A.
B.
C.
D.

tert-Butylbenzene
Ethylbenzene
Toluene
Styrene

11. What is the product of the following synthesis?

1) MeBr, FeBr3
2) Br2, light
3) NaOH, H2O
4) H2CrO4

A.
4

O
OH

B.
O
Br

C.
O
H

D.
12. Rank the following compounds in order of increasing acidity.
OH

OH

OH
NO2

Br

NO2

NO2

A.
B.
C.
D.

X<Y<Z
Z<Y<X
X<Z<Y
Y<X<Z

13. Which of the following products is formed in good yield by the reduction of methyl 4-oxo-hexanoate
(M) with NaBH4?
O
O
M

A.
B.
C.
D.

Methyl 4-hydroxyhexanoate
6-Hydroxy-3-hexanone
1,5-Hexanediol
4-Hydroxyhexanal

14. Which of the following statements about organometallic compounds is FALSE?

A.
B.
C.
D.

Alkyllithium reagents (RLi) add to the carbonyl group of aldehydes and ketones.
Grignard reagents (RMgBr) add to the carbonyl group of aldehydes and ketones.
Alkyllithium and Grignard reagents do not add to esters.
Grignard reagents are prepared in ether or tetrahydrofuran (THF).

15. Which compounds undergo nucleophilic addition and which undergo substitution?
W. (CH3)2C=O

A.
B.
C.
D.

X. CH3CH2CH2COCl

Y. CH3COOCH3

Z. C6H5CHO

W and X undergo addition; Y and Z undergo substitution.

Y and Z undergo addition; W and X undergo substitution.
X and Y undergo addition; W and Z undergo substitution.
W and Z undergo addition; X and Y undergo substitution.

Part 2: Questions that need short answers:

1. Draw product of the following Diels-Alder reaction. Please use appropriate curved arrows to indicate the
movement of all electrons that moved during the reaction. (20 points. The structure of the product worth
11 points; each arrow worth 3 points; stereochemistry is not required)
O

OMe
Heat

O
OMe

O
OMe

omitting re-draw the starting material and drawing the arrows on the orignial one is also OK

If stereochemistry of the product is given, it is even better. But this is not required for the test

2. Draw a stepwise mechanism for the following reaction. Please use appropriate curved arrows to indicate
the movement of all electrons that moved during the reaction. Please do not omit any important steps
(30 points. Each arrow and intermediates worth 3 points until 30 points are reached.)

AlCl3

HCl

Cl

AlCl3
Cl

Cl

AlCl3

AlCl4

Product

H
H
H

H
H

Each structure highlighted in red and each arrow highlighted in blue

worth 3 points until the maximum 30 points are reached

Writing side products as HCl and AlCl3 is OK; in this case, the
mechanism is slightly different and is more close to the writing in the book

3. Identify the lettered compounds in the following reaction sequence (30 points. A, 8 points; B, 8 points;
C, 7 points; and D, 7 points)
1) NaNH2
H

H
2) CH3I

1) NaNH2

2) CH3CH2I

A
H

1) O3
2) H2O

C + D

B
CH3

C or D
CH3CH2COOH

H3CH2C

CH3

C or D
CH3COOH

CH
H2420, Organic
O
C
Chemistr
ry II, Finaal Exam
3:005:000 PM, Aprill 26th, 2010 (total
(
300 pooints)

ur name CL
LEARLY heere:
Pleaase print you
Last,

TEST
T FORM

First

Makke sure you have

h
chosen the form of test that is different
d
from
m those chossen by the stuudents next to you; theree
are three forms, A, B and C,, which are printed
p
on paapers with diifferent coloors. The quesstions are thee same but
they and the answ
wers to them
m are arrangeed in differennt orders.
The exam has tw
wo parts. Parrt one containns 20 multipple choice quuestions. Thee total pointss for this parrt are 200
(10 20). Each question
q
hass only one coorrect answeer. You needd to mark youur answers of
o these quesstions with a
penccil on your annswer sheet.. This part will
w be gradedd using a scaanner. As a result,
r
answeers marked on
o the exam
will NOT be graaded. In addiition to answ
wers, please also
a fill the following
f
infformation onn your answer sheet: 1.
yourr name; 2. I. D. number, print it in thhe form and then
t
mark thhe corresponnding numbeers; 3. Test foorm number,
whicch is A forr you.
The second part of the exam
m contains 6 questions
q
thaat need shortt written ansswers. The tootal points foor this part
are 100.
1 Answerrs to these qu
uestions needd to be put inn the space provided
p
in the
t exam. Thhis part will be graded
manuually.
The total points for the final will be enteered into WeebCT. The annswer sheet for the multiiple choice questions
q
e
in my office
o
after the
t scores arre entered intto WebCT.
may not be returrned to you. You may picck up your exam
s
be abble to finish grading
g
befoore Thursdayy April 29th. You might want
w to checck the accuraacy of your
We should
total score in WeebCT beforee the grades are
a submitteed to the Reggistrar's Officce (I will sennd an email to remind
you, and will givve you one day
d to do thiss). The keys will be postted in ARIS and sent to you
y by emaiil. The
exam
ms that are not picked up
p will remainn in my officce for severaal weeks andd will then bee destroyed.

Part 1: Multiple choice questions.

1. Arrange the following compounds in order of decreasing chemical shift for the underlined hydrogens
(largest value first, smallest value last).
a) CH3OCH2CH3; b) CH3CH2CH3; c) Cl2CHCH2CH3; d) ClCH2CH2CH3
A)
B)
C)
D)

b>c>a>d
c>b>a>d
a>c>d>b
c>b>d>a

2. Which of the following statements regarding the DielsAlder reaction is TRUE?

A)
B)
C)
D)

The diene must be s-cis and the major product is usually the endo product.
The diene must be s-trans and the major product is the endo product.
The diene must be s-cis and the major product is the exo product.
The diene must be s-trans and the major product is the exo product.

3. When benzene undergoes hydrogenation in the presence of a catalyst, the energy that is released (the heat of
hydrogenation) is
A)
B)
C)
D)

the same as for cyclohexatriene.

the same as for 1,3-cyclohexadiene.
the same as for 1,4-cyclohexadiene.
less than for 1,3-cyclohexadiene.

4. Which of the following aromatic compounds undergoes FriedelCrafts alkylation with methyl chloride and
aluminum chloride?
A)
B)
C)
D)

benzoic acid
nitrobenzene
aniline
toluene

5. Which of the following compounds does NOT give benzoic acid when heated with alkaline potassium
permanganate?
A)
B)
C)
D)

tert-butylbenzene
ethylbenzene
toluene
styrene

6. Which of the following compounds does NOT give a tertiary alcohol upon reaction with excess
methylmagnesium bromide?
A)
B)
C)
D)

3-methylpentanal
ethyl benzoate
4,4-dimethylcyclohexanone
4-heptanone

7. Predict which of the following compounds will have a lower boiling point than 1-butanal.
A)
B)
C)
D)

1-butanol
2-butanol
1-butene
butanoic acid

8. What ylide is needed to make 3-ethyl-3-heptene from 3-pentanone in a Wittig reaction?

A)
B)
C)
D)

Ph3P=CH-CH2-CH3
Ph3P=CH(CH2CH3)2
Ph3P=CH-CH2CH2CH3
Ph3P=CH2

9. Which of the following compounds will react most rapidly with water?
A)
B)
C)
D)

acetone
acetyl chloride
acetic anhydride
ethyl acetate

10. What is the product formed when benzonitrile is treated with phenylmagnesium bromide followed by acid
hydrolysis?
A)
B)
C)
D)

benzophenone
benzyl alcohol
benzaldehyde
triphenylmethyl amine

11. Predict the product of the following reaction.

OEt
O

1. NaOEt, EtOH
2. PrBr
3. H3O , heat

A) 3-hexanone
B) 3-heptanone
3

C) ethyl pentanoate
D) 2-butanone
12. Which compound is formed when the enolate of 2-methylcyclohexanone, formed from lithium
diisopropylamide (LDA), reacts with methyl iodide?
O

A)
B)
C)
D)

OH

a
b
c
d

13. What is the starting material used in the following reaction?

O

Ph
OH

10% NaOH, H2O

OH

2X

2X

A)
B)
C)
D)

2X

2X

a
b
c
d

14. What is the major product of the following reaction?

NaOH
O
O

Heat

O
O

A)
B)
C)
D)

a
b
c
d

15. What is the name of the following compound?

Li

A)
B)
C)
D)

lithium diisopropylamine
lithium diisopropylamide
lithium diisopropylammonium
diisopropylamine anion

16. Predict the product of the following reaction.

Benzenediazonium chloride + CuCN
A)
B)
C)
D)

Ph2CuCl
PhCN
Ph2CuLi
PhN=NCN

17. Which of the following compounds form the highest percentage of gem-diol at equilibrium?
A)
B)
C)
D)

CH3CH2CH2CHO
CH3CH2COCH3
CH3CF2CHO
CH3CH2CHO

18. Rank the following compounds in order of increasing reactivity in nucleophilic acyl substitution.
CH3CH2CH2CONH2 (W); CH3CH2CH2COCl (X); CH3CH2CH2COOCH2CH2CH3 (Y); (CH3CH2CO)2O (Z)
A)
B)
C)
D)

W<X<Y<Z
Z<X<Y<W
W<Y<Z<X
W<Y<X<Z

19. Rank the labeled protons in each compound in order of increasing acidity.
Hy

Hx

O
O
1

A)
B)
C)
D)

Hx

Hz

Hy

Hz

In compound 1, Hx < Hy < Hz; In compound 2, Hx < Hy < Hz.

In compound 1, Hy < Hy < Hx; In compound 2, Hx < Hz < Hy.
In compound 1, Hz < Hy < Hx; In compound 2, Hy < Hz < Hx.
In compound 1, Hx < Hy < Hz; In compound 2, Hz < Hx < Hy.

20. Rank the following three compounds in the order of increasing basicity.
NH2

NH2

H
N
H

A)
B)
C)
D)

a<b<c
b<a<c
c<b<a
b<c<a

Part 2: Questions that need short answers:

1. Draw a stepwise mechanism for the following reaction. Please use appropriate curved arrows to indicate the
movement of all electrons that moved during the reaction. Please do not omit any important steps (15
points. Each intermediate structure worth 2 points; each curved arrow and side product worth 1 point until
15 points are reached.)
O
COOH
HO

H2SO4

H2O

H
O
HO

OH
H

H
HO

HO

H
H

H
O

HO

HO

OH
O

O
H2O

H
O
O

Each structure in red worth 2 points, each structure and curved arrow in blue worth 1
point. The total may not exceed 15 points. Drawing the equlibrium reaction arrow as
irreversible reaction arrow will not reduce points. Other appropriate drawings may be
considered correct.

2. Draw a stepwise mechanism for the following reaction. Please use appropriate curved arrows to indicate the
movement of all electrons that moved during the reaction. Please do not omit any important steps (20
points. Each intermediate worth 2 points; each curved arrow and side product worth 1 point until 20 points
are reached).
1) NaOEt
2)

CO2Et

O
O

CH2(CO2Et)2
O

3) H3O

EtO

O
OEt

EtO

EtO

OEt

EtO

O
O

OEt

HOEt

OEt
O

OEt

EtO

O
O

O
O

H3O

H
OEt

OEt

OEt
H
HOEt

EtO

Each structure in red worth 2 points, each structure and curved arrow in blue worth 1
point. The total may not exceed 20 points. Other appropriate drawings may also be
considered correct.

3. Fill in the lettered reagents (A-G) in the following reaction scheme (draw structures or write the names of
the reagents in the space below the scheme, please do not forget to label them with A-G. For some letter,
more than one step/reagent may be needed. Total 14 points).

OH
HO

CHO

COOH

HO

HO

H
B

HO
1) A

G
O

2) H2O
HO

Li

E TBDMS-Cl, imidazole

Si
O

OH

2) H2O

Ag2O, NH4OH

1) F

Si

1) BH3
2) H2O2, -OH

H2O, H2SO4, HgSO4

MeLi

TBAF or Bu4NF

Each anwser worth 2 points; other suitable reagents are also OK; omitting
reagents that are highlighted in red will not reduce points. Writing a name
instead of a structure or drawing a structure instead of a name will also be
considered correct.

4. Draw the organic products formed in the following three reactions. No mechanism is required; just need the
structure of the major final organic products (total 21 points).
1) LDA

O
(1)

OH

2) CH3CH2CHO
3) H2O

(2)

Ph

NaOCH3

Ph
+
O

CH3OH

O
B

CHO
(3)

O
HO

+
Ph

H2O

Ph

Drawing the Z
isomer is also OK

For A, elimination product will also be

considered correct. For B, if the aldol is
given, 5 points will be given. Each strucutre
worth 7 points. The total is 21 points.

10

5. Draw a stepwise mechanism for the following reaction. Please use appropriate curved arrows to indicate the
movement of all electrons that moved during the reaction. Please do not omit any important steps (15
points. Each intermediate worth 4 points and each curved arrow and side product worth 1 point until 15
points are reached).
O

NaBH4

H
N
H2O

CH3OH
NH2

H
H
OH

H
N

H
N

NH2
H2O

H
Each structure in red worth 4 points, each structure and curved arrow in blue worth 1
point. The total may not exceed 15 points. Other appropriate drawings may also be
considered correct.

11

6. Ethers are oxidized with O2 to form hydroperoxides that decompose violently when heated. Draw a stepwise
mechanism for this reaction. Make sure to use appropriate curved arrows to indicate the movement of all
electrons that moved during the reaction. (15 points. Each intermediate worth 3 points and each curved
arrow and side product worth 1 point until 15 points are reached)

O2

OOH

H
O

+
O

OH

Each structure in red worth 3 points, each structure and curved arrow in blue worth 1
point. The total may not exceed 15 points. Other appropriate drawings may be
considered correct. Drawing the single-headed arrow as double headed arrow will
only give 0.5 point. Omiting lone pairs on oxygen atoms is OK, but the unpaired
electrons cannot be omitted.

12

CH2420, Organic Chemistry II, Exam 1

2:003:00 PM, February 2nd, 2011 (total 200 points)

Please print your name CLEARLY here:

Last,

TEST FORM

First

Make sure you have chosen the form of test that is different from those chosen by the students next to you.
There are three forms, A, B and C, which are printed on papers with different colors. The questions are the
same but they and the answers to them are arranged in different orders.
The exam has two parts. Part one contains 10 multiple choice questions. The total points for this part are 160
(16 10). Each question has only one correct answer. You need to mark your answers of these questions with a
pencil on your answer sheet. This part will be graded using a scanner. As a result, answers marked on the exam
will NOT be graded. In addition to answers, please also fill the following information on your answer sheet: 1.
your name; 2. I. D. number, print it in the form and then mark the corresponding numbers; 3. Test form number,
which is A for you.
The second part of the exam contains 2 questions that need short written answers. The total points for this part
are 40 (20 2). Answers to these questions need to be put in the space provided in the exam. This part will be
graded manually.
The total points your earned will be entered into WebCT. The answer sheet for the multiple choice questions
may not be returned to you. You can pick up your exam in the Chemistry Learning Center after the points are
entered into WebCT (see syllabus for details). The keys will be posted in WebCT. I will send an email to the
class when ready.

Part 1: Multiple choice questions. (16 10 = 160 points)

1. Give the IUPAC name for the following compound:
CH 3

OH

A. trans-6-Methylcyclohexanol
B. cis-2-Methylcyclohexanol
C. cis-1-Hydroxymethylcyclohexane
D. trans-Cycloheptanol

2. What is the organic product of the following reaction?

CH2CH2I

OCH(CH3)2

A. The following unsymmetrical ether

CH2CH2OCH(CH3)2

B. The following terminal alkene

C. The following internal alkene

D. The following unsymmetrical ether

3. Rank the following alcohols in order of increasing reactivity when dehydrated with H2SO4.
CH3

OH

OH
HO

CH3

A. A is most reactive, B is least reactive, and C in between.

B. B is most reactive, C is least reactive, and A in between.
C. C is most reactive, A is least reactive, and B in between.
D. All are alcohols and therefore they have the same reactivity.

4. What is the major product formed when alcohol X is treated with HCl?
Cl
Cl
OH

Cl

A. A is the major product.

B. B is the major product.
C. C is the major product.
D. None of the above is correct.

5. What is the product of the following reaction? Pay attention to the stereochemistry of the reaction.
O
H3C

1) H
H

CH 3

OH

2) H2O

HO

HO

H
H

H
H 3C

H 3C

H3C

OH

A. Compound A.
B. Compound B.
C. Compound C.
D. Compound D.
3

6. The enantiomer of (1E, 4R)-1,4-dimethylcyclodecene is:

A. A. Its name is (1Z, 4R)-1,4-dimethylcyclodecene.

B. B. Its name is (1E, 4S)-1,4-dimethylcyclodecene.
C. C. Its name is (1E, 4S)-1,4-dimethylcyclodecene.
D. D. Its name is (1Z, 4R)-1,4-dimethylcyclodecene.

7. For the following reaction, the products are:

HBr

Br

Br
H

Br

Br

A. A and B; A is R enantiomer and B is the S enantiomer.

B. B and C; B is the R enantiomer and C is the S enantiomer.
C. B and C; B is the S enantiomer and C is the R enantiomer.
D. A and D; A is the S enantiomer and D is the R enantiomer.

8. Select the appropriate reagents to complete the following multistep synthesis.

Cl

Br
OH

A. Step 1: KOCH3; step 2: HCl.

B. Step 1: KO(CH3)3; step 2: Cl2, H2O.
C. Step 1: KO(CH3)3; step 2: Cl2.
D. Step 1: KO(CH3)3; step 2: HCl, H2O.
4

9. For the following multistep synthesis:

Br

OH
Br

Br

O
OH

A. (1) Use KOC(CH3)3 to convert the starting material to A; (2) use Br2/H2O to convert A to D; (3) use an acid
to convert D to the product.
B. (1) Use KOC(CH3)3 to convert the starting material to A; (2) use Br2/H2O to convert A to D; (3) use a base to
convert D to the product.
C. (1) Use KOC(CH3)3 to convert the starting material to C; (2) use Br2/H2O to convert C to D; (3) use a base to
convert D to the product.
D. (1) Use KOC(CH3)3 to convert the starting material to A; (2) use Br2/H2O to convert A to B; (3) use a base to
convert B to the product.

10. Can the following alcohol be prepared as a single product by hydroboration-oxidation of an alkene? Can it
be prepared as a single product be the acid-catalyzed addition of water to an alkene? Select the single best
answer.
OH

A. Yes, both methods give a single product.

B. No, both methods give product mixtures.
C. Only acid-catalyzed addition of water gives a single product.
D. Only hydroboration-oxidation gives a single product.

Part 2: Questions that need short answers. (20 2 = 40 points)

1. Draw a stepwise mechanism for the following reaction. Please use appropriate curved arrows to indicate the
movement of all electrons that moved during the reaction. Please do not omit any important steps (20 points.
Each intermediate structure worth 4 points; each curved arrow and side product worth 1 point until 20 points
are reached).

O
OH

S
Cl

Cl

Cl

Cl

O
OH

O
S

S
Cl

Cl

Cl

H
N
Cl

O
S
O

Cl

N
H

Cl

+ O

Cl

Total 20 points. Each structure in red worth 4 points; each curved arrow and
structure in green worth 1 point until 20 points are reached. So, you do not need to
be completely correct to get full points. Other correct drawings will also get points.

2. Draw a stepwise mechanism for the following reaction. Please use appropriate curved arrows to indicate the
movement of all electrons that moved during the reaction. Please do not omit any important steps (20 points.
Each intermediate structure worth 4 points; each curved arrow and side product worth 1 point until 20 points
are reached).

H3C

CH 3

CH 3

H3C

H2SO4

CH3

CH3
C

H3C

C
CH3

H3C

CH 3

CH 3

CH3

H3C

O
H

CH 3

CH3

CH 3

OH

O
H

OH
H2O

H3C

CH3

CH3

CH3
H

CH 3
H3C

CH3

CH3

H3C

CH3
C

H3C

C
CH3

H2C
H

CH 3

CH3

CH3
H

Total 20 points. Each structure in red worth 4 points; each curved arrow and
structure in green worth 1 point until 20 points are reached. So, you do not need to
be completely correct to get full points. Other correct drawings will also get points.

Next page has a short survey.

This is a voluntary anonymous survey. You can answer all or part of the questions. Please do not submit
with your exam. Instead, detach this page from the exam and put in the box located at the doors.
The goal is to help to improve teaching. Although I cannot follow all of your suggestions (they can be
contradictory to each other too), I believe that both you and I can benefit from them. Please do not let your
frustrations from COONECT to affect your answers.
1. How about the pace of the lectures? Can be somewhat faster? Or it is OK or it should be slower.

2. Can you hear me well at the back of the classroom? Are the slide show and project clear enough?

3. Do you like the grading policy? Do you know what materials you should review before an exam?

4. Are the numbers of questions in the homework OK for you? More or less is better?

5. Overall, how do you rank the course? If ranking from 1 to 5 with 1 being the least satisfactory and 5 being
the most satisfactory, which do you choose?

6. Any other comments are also appreciated.

CH2420, Organic Chemistry II, Exam 2

2:003:00 PM, March 16th, 2011 (total 200 points)

Please print your name CLEARLY here:

Last,

TEST FORM

First

Make sure you have chosen the form of test that is different from those chosen by the students next to you.
There are three forms, A, B and C, which are printed on papers with different colors. The questions are the
same but they and the answers to them are arranged in different orders.
The exam has two parts. Part one contains 20 multiple choice questions. The total points for this part are 140 (7
20). Each question has only one correct answer. You need to mark your answers of these questions with a
pencil on your answer sheet. This part will be graded using a scanner. As a result, answers marked on the exam
will NOT be graded. In addition to answers, please also fill the following information on your answer sheet: 1.
your name; 2. I. D. number, print it in the form and then mark the corresponding numbers; 3. Test form number,
which is A for you.
The second part of the exam contains 2 questions that need short written answers. The total points for this part
are 60 (30 2). Answers to these questions need to be put in the space provided in the exam. This part will be
graded manually.
The total points you earned will be entered into WebCT. The answer sheet for the multiple choice questions
may not be returned to you. You can pick up your exam in the Chemistry Learning Center after the points are
entered into WebCT (see syllabus for details). The keys will be posted in WebCT. I will send an email to the
class when ready.

Part 1: Multiple choice questions. (7 20 = 140 points)

1. What is the product of the following reaction? Pay attention to the stereochemistry of the reaction.
O
H3C

1) H
H

CH 3

OH

2) H2O

HO

HO

H
H

H
H 3C

H 3C

H3C

OH

A. Compound A.
B. Compound B.
C. Compound C.
D. Compound D.
2. Rank the following compounds in order of increasing boiling point.
Compound A: CH3CH2OCH3
Compound B: CH3CH2CH2OH
Compound C: (CH3)2CHOH
A. Compound A has the highest boiling point; compound B has the lowest boiling point.
B. Compound B has the highest boiling point; compound A has the lowest boiling point.
C. Compound C has the highest boiling point; compound A has the lowest boiling point.
D. Compound B has the highest boiling point; compound C has the lowest boiling point.
3. The enantiomer of (1E, 4R)-1,4-dimethylcyclodecene is:

A. A. Its name is (1Z, 4R)-1,4-dimethylcyclodecene.

B. B. Its name is (1E, 4S)-1,4-dimethylcyclodecene.
C. C. Its name is (1E, 4S)-1,4-dimethylcyclodecene.
D. D. Its name is (1Z, 4R)-1,4-dimethylcyclodecene.
2

4. What is the major organic product of the following reaction?

A. Compound A.
B. Compound B.
C. Compound C.
D. Compound D.
5. The major organic product of the following two reactions are:

H2O, H2SO4, HgSO4

BH3, then H2O2, HOB

OH

OH
W

A. Product A is W; product B is Z.
B. Product A is Z; product B is W.
C. Product A is X; product B is Y.
D. Product A is Y; product B is X.
6. What reagents are needed to prepare CH3CH2CH2CH2CCH from CH3CH2CH2CH2CH=CH2?
A. HBr; KOC(CH3)3 (2 equivalents) in DMSO.
B. POCl3 in pyridine; NaH.
C. Cl2; KOC(CH3)3 (2 equivalents) in DMSO.
D. BH3; H2O2, HO-.
3

7. Identify the compounds in the following multi-step reaction.

A. Compound A is W; Compound B is Y; Compound C is Z.

B. Compound A is Z; Compound B is Y; Compound C is W.
C. Compound A is X; Compound B is Y; Compound C is W.
D. Compound A is W; Compound B is X; Compound C is Z.
8. Which bases can deprotonate acetylene, which has a pKa of 25.
A. CH3CH2S- (pKa of conjugate acid is 10.5) and CH2=CH- (pKa of conjugate acid is 44).
B. CH3CH2O- (pKa of conjugate acid is 16) and CH3NH- (pKa of conjugate acid is 40).
C. CH3CH2S- (pKa of conjugate acid is 10.5) and CH3CH2O- (pKa of conjugate acid is 16).
D. CH2=CH- (pKa of conjugate acid is 44) and CH3NH- (pKa of conjugate acid is 40).

9. What is the major organic product of the following reaction?

A. Compound W.
B. Compound X.
C. Compound Y.
D. Compound Z.
10. Oximene and myrcene, two hydrocarbons isolated from alfalfa that have the molecular formula C10H16, both
yield 2,6dimethyloctane when treated with H2 and a Pd catalyst. Ozonolysis of oximene forms (CH3)2C=O,
CH2=O, CH2(CHO)2, and CH3COCHO. Ozonolysis of myrcene yields (CH3)2C=O, CH2=O (two equiv), and
HCOCH2CH2COCHO. Identify the structures of oximene and myrcene.

A. Oximene is X; myrcene is Z.
B. Oximene is Y; myrcene is W.
C. Oximene is X; myrcene is Y.
D. Oximene is Y; myrcene is X.

11. Rank the following alkenes in order of increasing rate of reaction with H2, Pd-C.

A. Compound X is most reactive; compound Z is least reactive.

B. Compound Y is most reactive; compound Z is least reactive.
C. Compound Z is most reactive; compound Y is least reactive.
D. They have the same reactivity.
12. What product is formed, including stereochemistry, when CH3OCH2CH2CCH2CH(CH3)2 is treated with
Na in liquid NH3?

A. Compound W.
B. Compound X.
C. Compound Y.
D. Compound Z.
13. From the list below, select all of the structures for a hydrocarbon with a molecular ion at m/z = 112 in mass
spectra.

O
OH
T

A. Compounds S, T, Y, X.
B. Compounds U, T, V, X.
C. Compounds S, W, Y, Z.
D. Compounds T, V, Y, Z.
14. What are the major IR absorptions in the functional group region for the following compound?

U: 3300 cm-1; V: 1650 cm-1; W: 3150-3000 cm-1; X: 3000-2850 cm-1; Y: 2250 cm-1; Z: 3500 cm-1.
A. U, W, X.
B. W, X, V.
C. Y, W, Z.
D. V, W, Y.
15. In the IR spectrum of an organic compound, in the functional group region, there are only two absorptions.
One is at ~2950 cm-1, the other is at ~1750 cm-1. The structure of the compound is most likely to be:
O

OH
O

OH

O
X

A. Compounds V and W
B. Compounds X and Y
C. Compounds W and Z
D. Can only be compound U.

16. Which of the following compounds are consistent with the following set of data: a hydrocarbon with a
molecular ion at m/z = 68, and IR absorptions at 3310 cm-1, 3000-2850 cm-1, and 2120 cm-1.

A. Compounds U and Y.
B. Compounds S and X.
C. Compounds V and T.
D. Compounds W and Z.
17. The 1H NMR spectrum of 1,2-dimethoxyethane recorded on a 300 MHz spectrometer consists of signals at
1017 Hz and 1065 Hz downfield from TMS. What are the chemical shifts of the two absorptions?
A. 4.39 ppm and 4.55 ppm.
B. 1.39 ppm and 1.55 ppm.
C. 2.39 ppm and 2.55 ppm.
D. 3.39 ppm and 3.55 ppm.
18. A molecule has the molecular formula of C7H14O2. Its 1H NMR data are 0.93 ppm (doublet, 6 H), 1.15 ppm
(triplet, 3 H), 1.91 ppm (multiplet, 1 H), 2.33 ppm (quartet, 2H), 3.86 ppm (doublet, 2H). What is the
compound?

A. Compound W.
B. Compound X.
C. Compound Y.
D. Compound Z.

19. Which of the following compounds give one singlet in 1H NMR spectra?
O
Cl

Cl
Br

Br

Br

Br

Br

O
Y

A. Compounds S, U, X, Z.
B. Compounds T, V, X, Y.
C. Compounds T, U, W, Z.
D. Compounds S, U, W, Z.
20. Rank the indicated carbon atoms in order of increasing chemical shift.

A. Carbon X has the smallest chemical shift; carbon Y has the largest chemical shift.
B. Carbon Y has the smallest chemical shift; carbon X has the largest chemical shift.
C. Carbon X has the smallest chemical shift; carbon Z has the largest chemical shift.
D. Carbon Z has the smallest chemical shift; carbon X has the largest chemical shift.

Part 2: Questions that need short answers. (30 2 = 60 points)

1. Draw a stepwise mechanism for the following reaction. Please use appropriate curved arrows to indicate the
movement of all electrons that moved during the reaction. Please do not omit any important steps (30 points.
Each intermediate structure worth 4 points; each curved arrow and other items worth 2 points until 30 points
are reached).

H2O

H+

H
H3C

CH3
H 3C

+
O

H+
H

CH 3
H 3C

CH3

Either E or Z is OK

H
H

H3C
H

CH3
+

H
H3C H

O
CH3

H 3C H

H
+O

CH3

H+
H
H3C H

O
CH3

Total 30 points. Each structure in red worth 4 points; each curved arrow and structure
in green worth 2 points until 30 points are reached. So, you do not need to be
completely correct to get full points. Other correct drawings will also get points.

10

2. Draw a stepwise mechanism for the following reaction. Please use appropriate curved arrows to indicate the
movement of all electrons that moved during the reaction. Please do not omit any important steps (30 points.
Each intermediate structure worth 4 points; each curved arrow and other items worth 2 points until 30 points
are reached).
Na, NH3 (liquid)
R

H
N
R

R
Na

Na

+ e

e-

H
H
H 2N-

+
H

R
C

R
R

+ H 2N-

C
-

H
N
H

Total 30 points. Each structure in red worth 4 points; each curved arrow and structure
in green worth 2 points until 30 points are reached. So, you do not need to be
completely correct to get full points. Other correct drawings will also get points.

11

CH2420, Organic Chemistry II, Exam Final

3:005:00 PM, April 25th, 2011 (total 300 points)

Please print your name CLEARLY here:

Last,

TEST FORM

First

Make sure you have chosen the form of test that is different from those chosen by the students next to you.
There are three forms, A, B and C, which are printed on papers of different colors. The questions are the same
but they and the answers to them are arranged in different orders.
The exam has three parts. The first part contains 20 multiple choice questions. The total points for this part are
180 (9 20). Each question has only one correct answer. You need to mark your answers of these questions
with a pencil on your answer sheet. This part will be graded using a scanner. As a result, answers marked on the
exam will NOT be graded. In addition to answers, please also fill the following information on your answer
sheet: 1. your name; 2. I. D. number, print it in the form and then mark the corresponding numbers; 3. Test form
number, which is A for you.
The second part contains 5 questions that need you to draw the structure of organic reaction products. The total
points for this part are 50 (10 5). Answers to these questions need to be put in the space provided in the exam.
This part will be graded manually.
The third part contains 3 questions that need you to provide stepwise mechanism of organic reactions. The total
points for this part are 70 (20 + 25 + 25). Answers to these questions need to be put in the space provided in the
exam. This part will be graded manually.
The total points you earned will be entered into WebCT. The keys will be posted in WebCT. I will send an
email to the class when ready. For grading policy, please see Syllabus.

Part 1: Multiple Choice Questions. (9 20 = 180 points)

1. Fill in the intermediate products in the following multiple step synthesis.
CH3CH2Cl

Cl2

AlCl3

FeCl3

Br2
Heat

HNO3

mCPBA

KOtBu

[+ o isomer]

H2SO4

Cl

Cl

Cl

Cl

NO2

NO2

Br

5
Cl

Cl
O

Cl

NO2

Cl

NO2

Cl

NO2

Br

NO2

O2N

10

Br

Cl

Cl
NO2

11

NO2

12

Cl

13
NO2

Br

NO2

14

Br
NO2

15

A. Compounds U, V, W, X, Y and Z are 2, 3, 10, 11, 12 and 13, respectively.

B. Compounds U, V, W, X, Y and Z are 2, 1, 4, 6, 7 and 8, respectively.
C. Compounds U, V, W, X, Y and Z are 2, 1, 5, 11, 12 and 13, respectively.
D. Compounds U, V, W, X, Y and Z are 2, 3, 10, 9, 14 and 15, respectively.
2. What reagent(s) is/are needed to convert 1ethylcyclohexene into1,2dibromo1ethylcyclohexane?
A. H2, PdC
B. HBr, ROOR
C. HBr
D. Br2

3. Match 1H NMR spectra with compounds.

OH
O

OH

A. Spectrum E is from compound W, and spectrum F is from compound X.

B. Spectrum E is from compound X, and spectrum F is from compound Y.
C. Spectrum E is from compound X, and spectrum F is from compound Z.
D. Spectrum E is from compound Z, and spectrum F is from compound X.
4. Which of the following compounds are aromatic?
H
N

O
N

S
O

A. Compounds S, T, U, V only.
B. Compounds W, X, Y, Z only.
C. Compounds S, T, U, V, X, Z only.
D. All are aromatic.

5. Consider both 5methyl1,3cyclopentadiene (Y) and 7methyl1,3,5cycloheptatriene (Z), which labeled

H atom is most acidic? Which labeled H atom is least acidic?

A. Hc is most acidic because its conjugate base is antiaromatic; Hd is least acidic because its conjugate base is
aromatic.
B. Hb is most acidic because its conjugate base is aromatic; Hc is least acidic because its conjugate base is
antiaromatic.
C. Hd is most acidic because its conjugate base is aromatic; Hb is least acidic because its conjugate base is
antiaromatic.
D. Ha is most acidic because its conjugate base is antiaromatic; Ha is least acidic because its conjugate base is
aromatic.
6. Rank the following three compounds in order of increasing reactivity in electrophilic aromatic substitution
reactions.

A. X < Y < Z.
B. Y < X < Z.
C. Z < Y < X.
D. Z < X < Y.
7. Add reagents for the following multiple step synthesis.

A. W, X, Y and Z are CH3CH2COCl/AlCl3; Br2/FeBr3; Zn(Hg)/HCl; HNO3/H2SO4, respectively.

B. W, X, Y and Z are CH3CH2COCl; Br2/FeBr3; Zn(Hg)/HCl; HNO3/H2SO4, respectively.
C. W, X, Y and Z are CH3CH2COCl/AlCl3; Br2/heat; Zn(Hg)/HCl; HNO3/H2SO4, respectively.
D. W, X, Y and Z are CH3CH2COCl/AlCl3; Br2/FeBr3; mCPBA; SO3/H2SO4, respectively.
4

8. Match the following structures to the appropriate pKa values.

A. The pKa of compounds V, W, X, Y and Z are 4.8, 2.86, 2.8, 1.3 and 0.6, respectively.
B. The pKa of compounds V, W, X, Y and Z are 2.8, 4.8, 0.6, 1.3 and 2.86, respectively.
C. The pKa of compounds V, W, X, Y and Z are 2.8, 1.3, 0.6, 4.8 and 2.86, respectively.
D. The pKa of compounds V, W, X, Y and Z are 2.86, 4.8, 0.6, 1.3 and 2.8, respectively.
9. Select all that apply.
p Hydroxybenzoic acid is less acidic than benzoic acid, o hydroxybenzoic acid is
slightly more acidic than benzoic acid. Select all statements that explain this result.

Statement U: In the p form, the OH group withdraws electron density by its resonance effect
Statement V: In the p form, the OH group stabilizes the conjugate base.
Statement W: In the o form, intramolecular hydrogen bonding destabilizes the conjugate base
Statement X: In the p form, the OH group destabilizes the conjugate base.
Statement Y: In the o form, intramolecular hydrogen bonding stabilizes the conjugate base.
Statement Z: In the p form, the OH group donates electron density by its resonance effect
A. Statements U, V, W.
B. Statements X, Y, Z.
C. Statements W, X, Y.
D. Statements U, W, Y.
10. Explain why 2,2,5,5tetramethyl3hexyne can't be made using acetylide anions. Select
the single best answer.
A. The 1 alkyl halide is too crowded for nucleophilic substitution.
B. It has an internal alkyne; and internal alkynes cannot be made using acetylide anions.
C. The 2 alkyl halide is too crowded for nucleophilic substitution.
D. The 3 alkyl halide is too crowded for nucleophilic substitution.
5

11. Which of the following compounds matches or match the IR spectrum shown?

OH
OH

A. U, X and Z.
B. V, W and Y.
C. Only U.
D. Only X.
12. Which of the following reagents/conditions are appropriate to convert compound Y to compound Z?

A. First HBr, then PCC.

B. First Br2/heat, then KOtBu.
C. First mCPBA, then H2/Lindlar catalyst.
D. First Br2/heat, then HBr.
6

13. Assign carbon-13 NMR signals to each carbon in the compound shown.

A. C1, C2, C3 and C4 appear at 23, 70, 32 and 10 ppm, respectively.

B. C1, C2, C3 and C4 appear at 70, 23, 32 and 10 ppm, respectively.
C. C1, C2, C3 and C4 appear at 32, 70, 23 and 10 ppm, respectively.
D. C1, C2, C3 and C4 appear at 10, 70, 32 and 23 ppm, respectively.
14. Match structures to mass spectra.

Cl
O

Br
O

A. Mass spectra 1, 2 and 3 are from compounds X, Y and Z, respectively.

B. Mass spectra 1, 2 and 3 are from compounds X, Y and Z, respectively.
C. Mass spectra 1, 2 and 3 are from compounds X, Y and Z, respectively.
D. Mass spectra 1, 2 and 3 are from compounds Y, Z and X, respectively.

15. Provide reagents for the following multistep synthesis.

X

Cl

OH

Y
O

OH
+ enantiomer

A. Reagent X is Cl2 and water; reagent Y is NaH; reagent Z is first NaCCH, then water.
B. Reagent X is first Cl2, then water; reagent Y is HCl; reagent Z is NaCCH and water.
C. Reagent X is Cl2 and water; reagent Y is NaH; reagent Z is first water, then NaCCH.
D. Reagent X is Cl2; reagent Y is NaH; reagent Z is first NaCCH, then water.
16. Alkyne S is treated with O3 followed by water. Which of the following statements are correct?

S
Statement T: One product is an epoxide.
Statement U: The only product is benzoic acid.
Statement V: One product is an alcohol.
Statement W: More than one organic product will be formed.
Statement X: Only one organic product will be formed.
Statement Y: The product is a carboxylic acid.
Statement Z: One product is an aldehyde.
A. Only statements T, U, W are correct.
B. Only statements U, X, Y are correct.
C. Only statements W, Y, Z are correct.
D. Only statements W, T, V are correct.
17. Which compound absorbs UV light at the longest wave length?

A. Compound W.
B. Compound X.
C. Compound Y.
D. Compound Z.

18. What is the most stable 1,2-shift product of carbocation V?

A. Carbocation W.
B. Carbocation X.
C. Carbocation Y.
D. Carbocation Z.
19. Rank the following dienophiles in order of increasing reactivity in Diels Alder reactions.

A. X < Y < Z.
B. Z < Y < X.
C. Y < X < Z.
D. X < Z < Y.

20. Using the pKa values given, which of the following bases are strong enough to deprotonate CH3COOH
(pKa = 4.8)?

A. All of the above bases are strong enough.

B. Only bases Y and W are strong enough.
C. Only bases Z and V are strong enough.
D. Only bases V, Z and X are strong enough.

10

Part 2: Reaction Products. (10 5 = 50 points)

Draw the structure of the organic products of the following reactions. Try your best to draw accurately as partial
points may not be given due to the difficulty to be fair in that case.

Reaction 2:
HBr
40 oC
(Hint: There are two products, please draw both and
indicate which is the major product and which is the
minor one. The reaction occurs in an ionic media and
under thermodynamic control)

11

12

13

Part 3: Mechanism of Organic Reactions. (20 + 25 +25 = 70 points)

1. Draw a stepwise mechanism for the following reaction. Please use appropriate curved arrows to indicate the
movement of all electrons that moved during the reaction. Please do not omit any important steps (20 points.
Each intermediate structure worth 3 points; each curved arrow and other items worth 1 point until 20 points
are reached).

H
N

R
Na

Na

+ e

H
H2N-

+
H

R
C

R
R

H2N-

e-

C
-

H
N
H

Total 20 points. Each structure in red worth 3 points; each curved arrow and structure
in green worth 1 point until 20 points are reached. So, you do not need to be
completely correct to get full points. Other correct drawings will also get points.

14

2. Draw a stepwise mechanism for the following reaction. Please use appropriate curved arrows to indicate the
movement of all electrons that moved during the reaction. Please do not omit any important steps (25 points.
Each intermediate structure worth 5 points; each curved arrow and other items worth 1 point until 25 points
are reached).

AlCl4
H3C

Cl

CH3 H

CH3 H

CH3 H
H3C

CH3

Cl

AlCl3

CH3

H3C

CH3

CH3 H
CH3

H
H

Cl
HCl

CH3

AlCl3

H3C

CH3

CH3 H
H3C

H3C

CH3

H
H

AlCl3

AlCl3

Total 25 points. Each structure in red worth 5 points; each curved arrow and structure
in green worth 1 point until 25 points are reached. So, you do not need to be
completely correct to get full points. Other correct drawings will also get points.

15

3. Draw a stepwise mechanism for the following reaction. Please use appropriate curved arrows to indicate the
movement of all electrons that moved during the reaction. Please do not omit any important steps (25 points.
Each intermediate structure worth 10 points; each curved arrow and other items worth 1 point until 25 points
are reached).

R
R

O
O

Cr

Cr
O

OH

Cr

H
O
H
O

OH
O

Cr

H
O

Omitting the lone pair is OK

Total 25 points. Each structure in red worth 10 points; each curved arrow and structure
in green worth 1 point until 25 points are reached. So, you do not need to be
completely correct to get full points. Other correct drawings will also get points.

16

CH2420, Organic Chemistry II, Exam 1

2:003:00 PM, February 1st, 2012 (total 200 points)

Please print your name CLEARLY here:

Last,

First

TEST FORM A
Make sure you have chosen the form of test that is different from those chosen by the students next to you.
There are three forms, A, B and C, which are printed on papers with different colors. The questions are the
same but they and the answers to them are arranged in different orders.
The exam has two parts. Part one contains 15 multiple choice questions. The total points for this part are 150
(15 10). Each question has only one correct answer. You need to mark your answers of these questions with a
pencil on your answer sheet. This part will be graded using a scanner. As a result, answers marked on the exam
will NOT be graded. In addition to answers, please also fill the following information on your answer sheet: 1.
your name; 2. I. D. number, print it in the form and then mark the corresponding numbers; 3. Test form number,
which is A for you.
The second part of the exam contains 2 questions that need short written answers. The total points for this part
are 50 (25 2). Answers to these questions need to be put in the space provided in the exam. This part will be
graded manually.
The total points you earned will be entered into Blackboard. The answer sheet for the multiple choice questions
may not be returned to you. You can pick up your exam in the Chemistry Learning Center after the points are
entered into Blackboard (see syllabus for details). The keys will be posted in Blackboard. I will send an email to
the class when ready.

Part 1: Multiple choice questions. (15 10 = 150 points)

1. Devise a synthesis of CH3CH2CH2CHO (Z) from two-carbon starting materials.
(a)

(c)

NaH

1) BH3
2) H2O2, OH-

(b)

(d)

CH3CH2Br
(e)

(g)

(i)

A.
B.
C.
D.

(h)

NaNH2
(2 equiv)

(k)

(f)

(1) BH3
(2) H2O2, OHBrCH2CHO

(j)

(l)

Y
Y

Br2

HBr

BrCH2CH2OH

Y
H2O, H2SO4
HgSO4

H2O, H2SO4
HgSO4
Na, NH3

Z
Z

Reactions (a), (e), and (i)

Reactions (d), (g), and (k)
Reactions (a), (e), and (j)
Reactions (b), (f), and (l)

2. What is the product of the following reaction?

O

1) LiAlH4
2) H2O

OH

OH

H
OH

OH

A.
B.
C.
D.

OH

The product is W
The product is X
The product is Y
The product is Z

3. The alkyne R is treated with O3 followed by water, what are/is the product(s)?

O
O

S
O

O
OH

O
OH

A.
B.
C.
D.

The only product is V

The products are S, T and U
The products are Y and Z
The products are W and X

4. Select reactions that convert cis-2-butene to trans-2-butene.

(c)

(e)

A.
B.
C.
D.

Br2

HBr

(a)

CH3CO3H

X
Y

(b)

(d)

Na, NH3

NaNH2 (2 equiv)

H2, Lindlar catalyst

(f)

Reactions (a), (c) and (e)

Reactions (b), (d) and (f)
Reactions (a), (c) and (f)
Reactions (b), (d) and (e)

5. Pyridinium chlorochromate (PCC) is a commercially available reagent that provides Cr6+ (as CrO3), and does
not contain water. It is useful for oxidizing primary alcohols to aldehydes, and secondary alcohols to ketones.
Which of the following compounds does NOT give an aldehyde upon reaction with PCC?
A.
B.
C.
D.

Benzyl alcohol
Cyclopentylmethanol
2,2-Dimethyl-1-butanol
3-Methyl-3-pentanol
3

6. Which of the following reactions can be used for the synthesis of diol X and its enantiomer?
H

HO
H
Ph

Ph

(a)
Ph

Ph

(c)
Ph

A.
B.
C.
D.

1) OsO4

Ph

OH

1) OsO4

Ph

2) NaHSO3, H2O

1) CH3CO3H

Ph

2) OH-, H2O

(b)

2) NaHSO3, H2O

Ph

1) CH3CO3H
2) OH-, H2O

(d)
Ph

Reactions (a) and (c)

Reactions (b) and (d)
Reactions (a) and (d)
Reactions (b) and (c)

7. What is the product of the following reaction? Pay attention to the stereochemistry of the reaction.

A. Compound A
B. Compound B
C. Compound C
D. Compound D

8. The major organic products of the following two reactions are:

A. Product A is X; product B is Y
B. Product A is Z; product B is W
C. Product A is W; product B is Z
D. Product A is Y; product B is X
9. Which of the following is the MOST acidic?
A. 2-Butyne
B. 1-Butyne
C. 1-Butene
D. Butane
10. The major product of the reaction of 2,2-dichloropropane and excess NaNH2 is
A. Propyne
B. 1,2-Propadiene
C. 2-Chloropropene
D. 2-Chloropropane
11. Predict the product of the reaction of 1-pentyne and excess Br2.
A. 1,1-Dibromo-1-pentene
B. 1,2-Dibromo-1-pentene
C. 1,1,2,2-Tetrabromopentane
D. 2,2-Dibromo-1-pentene

12. The metal-catalyzed addition of hydrogen to an alkene occurs in what fashion?

A.
B.
C.
D.

Anti
A mixture of syn and anti
Neither syn or anti
Syn

13. Indicate the product resulting from the hydrogenation (excess H2/Pd on carbon) of 2-hexyne.
A.
B.
C.
D.

(Z)-2-Hexene
(E)-2-Hexene
Hexane
1-Hexene

14. What 10-carbon compound will undergo ozonolysis to give 2,4-pentadione as the only product?
A.
B.
C.
D.

1,2-Dimethylcyclopropene
1,6-Cyclodecadiene
1,2,4,5-Tetramethyl-1,4-cyclohexadiene
2,4-Dimethyl-1,4-cyclooctadiene

15. Which starting materials can be used to make the alkyne S?

A.
B.
C.
D.

T, V and Y
T, W and Y
U, V and Z
W, X and Z

Part 2: Questions that need short answers. (25 2 = 50 points)

1. Draw a stepwise mechanism for the following reaction. Please use appropriate curved arrows to indicate the
movement of all electrons that moved during the reaction. Please do not omit any important steps (25 points.
Each intermediate structure worth 3 points; each curved arrow and other items worth 2 points until 25 points
are reached).

H3C

H2O

H+

CH3
H3C

+
O

H+
H

CH3
H3C

CH3

Either E or Z is OK

H
H

H
O

H3C

CH3

H+

H
H3C H

O
CH3

H
H3C H

H
+O
CH3

H+
H
H3C H

O
CH3

Total 25 points. Each structure in red worth 3 points; each curved arrow and structure in
green worth 2 points until 25 points are reached. So, the students do not need to be
completely correct to get full points. Other correct drawings should be graded appropriately.

2. Draw a stepwise mechanism for the following reaction. Please use appropriate curved arrows to indicate the
movement of all electrons that moved during the reaction. Please do not omit any important steps (25 points.
Each intermediate structure worth 9 points; each curved arrow and other items worth 1 point until 25 points
are reached).
R
R

O Cr

R
R

O Cr

O
Cr

H
O

C
H

OH

O
Cr
O

O
H

OH
O

Cr

O-

Omitting the lone pair is OK

Total 25 points. Each structure in red worth 9 points; each curved arrow and structure
in green worth 1 point until 25 points are reached. So, the students do not need to be
completely correct to get full points. Other correct drawings will also get points.

The next page (page 9) has a voluntary anonymous survey.

This is a voluntary anonymous survey. You can answer all or part of the questions. Please do not submit
with your exam. Instead, detach this page from the exam and give it to a TA separately.
The goal is to help to improve teaching. Even though I cannot follow all of your suggestions (they can be
contradictory to each other too), I believe that both you and I will benefit from information you give.
1. How about the pace of the lectures? Can be somewhat faster? Or it is OK or it should be slower.

2. Can you hear me well at the back of the classroom? Are the slide show and projector clear enough?

3. From your experience so far, how do you rank the course? If ranking from 1 to 5 with 1 being the least
satisfactory and 5 being the most satisfactory, which do you choose?

4. Any other comments are also appreciated although I may not be able to follow.

CH2420, Organic Chemistry II, Exam 2

2:003:00 PM, March 21st, 2012 (total 200 points)

Please print your name CLEARLY here:

Last,
TEST FORM

First
A

Make sure you have chosen the form of test that is different from those chosen by the students next to you.
There are three forms, A, B and C, which are printed on papers with different colors. The questions are the
same but they and the answers to them are arranged in different orders.
The exam has two parts. Part one contains 15 multiple choice questions. The total points for this part are 150
(15 10). Each question has only one correct answer. You need to mark your answers of these questions with a
pencil on your answer sheet. This part will be graded using a scanner. As a result, answers marked on the exam
will NOT be graded. In addition to answers, please also fill the following information on your answer sheet: 1.
your name; 2. I. D. number, print it in the form and then mark the corresponding numbers; 3. Test form number,
which is A for you.
The second part of the exam contains 2 questions that need short written answers. The total points for this part
are 50 (25 2). Answers to these questions need to be put in the space provided in the exam. This part will be
graded manually.
The points you earned will be entered into Blackboard. The answer sheet for the multiple choice questions may
not be returned to you. You can pick up your exam in the Chemistry Learning Center after the points are
entered into Blackboard (see syllabus for details). The keys will be posted in Blackboard. I will send an email to
the class when ready.

Part 1: Multiple choice questions. (15 10 = 150 points)

1. The major organic products of the following two reactions are:

A. Product A is X; product B is Y
B. Product A is Z; product B is W
C. Product A is W; product B is Z
D. Product A is Y; product B is X
2. Why is the following compound not aromatic?

A. It has 4n electrons
B. It isn't planar
C. It has 4n+2 electrons
D. The electron system is not continuous
3. What are the major IR absorptions in the functional group region for the following compound?

U: 3300 cm-1; V: 1650 cm-1; W: 3150-3000 cm-1; X: 3000-2850 cm-1; Y: 2250 cm-1; Z: 3500 cm-1.
A. U, W, X
B. W, X, V
C. Y, W, Z
D. V, W, Y

4. Which of the following compounds are aromatic?

A. Compounds S, T, U, V only
B. Compounds W, X, Y, Z only
C. Compounds S, T, U, V, X, Z only
D. All are aromatic
5. What 10-carbon compound will undergo ozonolysis to give 2,4-pentadione as the only product?
A.
B.
C.
D.

1,2-Dimethylcyclopropene
1,6-Cyclodecadiene
1,2,4,5-Tetramethyl-1,4-cyclohexadiene
2,4-Dimethyl-1,4-cyclooctadiene

6. The 1H NMR spectrum of 1,2-dimethoxyethane recorded on a 300 MHz spectrometer consists of signals at
1017 Hz and 1065 Hz downfield from TMS. What are the chemical shifts of the two absorptions?
A. 4.39 ppm and 4.55 ppm
B. 1.39 ppm and 1.55 ppm
C. 2.39 ppm and 2.55 ppm
D. 3.39 ppm and 3.55 ppm
7. Which of the following statements is true about free radical halogenation of alkanes?
A. The first of the chain-propagating steps is rate-determining
B. The reaction proceeds by way of a flat sp2 hybridized free radical
C. The chain-initiating step involves cleavage of a carbon-hydrogen bond to afford a carbon radical and a
hydrogen atom
D. Both statements A and B are true

8. Which of the following compounds give one singlet in 1H NMR spectra?

O
Cl

Cl
Br

Br

Br

Br
T

Br

O
Y

A. Compounds S, U, X, Z
B. Compounds T, V, X, Y
C. Compounds T, U, W, Z
D. Compounds S, U, W, Z
9. Consider both 5methyl1,3cyclopentadiene (Y) and 7methyl1,3,5cycloheptatriene (Z), which labeled
H atom is most acidic? Which labeled H atom is least acidic?

A. Hc is most acidic because its conjugate base is antiaromatic; Hd is least acidic because its conjugate base is
aromatic
B. Hb is most acidic because its conjugate base is aromatic; Hc is least acidic because its conjugate base is
antiaromatic
C. Hd is most acidic because its conjugate base is aromatic; Hb is least acidic because its conjugate base is
antiaromatic
D. Ha is most acidic because its conjugate base is antiaromatic; Ha is least acidic because its conjugate base is
aromatic
10. Which molecule absorbs UV light at the longest wavelength?
A.
B.
C.
D.

1,3-heptadiene
1,4,7-octatriene
1,4-pentadiene
1,4-cyclohexadiene

11. Which of the following reagents/conditions are appropriate to convert compound Y to compound Z?

A. First HBr, then PCC

B. First Br2/heat, then KOtBu
C. First mCPBA, then H2/Lindlar catalyst
D. First Br2/heat, then HBr
12. A molecule has the molecular formula of C7H14O2. Its 1H NMR data are 0.93 ppm (doublet, 6 H), 1.15 ppm
(triplet, 3 H), 1.91 ppm (multiplet, 1 H), 2.33 ppm (quartet, 2H), 3.86 ppm (doublet, 2H). What is the
compound?

A. Compound W
B. Compound X
C. Compound Y
D. Compound Z
13. What will the product(s) be when compound W is reacted with NBS and UV light?

A. X only
B. Y only
C. Z only
D. Y and Z

14. Which of the following statements about the Diels-Alder reaction is false?
A. The reaction is stereospecific
B. The diene must be in the s-cis conformation in order to react
C. The dienophile usually contains an electron withdrawing group for the reaction to be synthetically useful
D. The diene and dienophile line up so that the exo product is kinetically favored
15. Which of the following molecules would give an IR spectrum with the following peaks: 1650 cm-1; 2900
cm-1; 3040 cm-1; 3300 cm-1 (weak); 3400 cm-1 (weak)

A.
B.
C.
D.

Compound W
Compound X
Compound Y
Compound Z

E. Part 2: Questions that need short answers. (25 2 = 50 points)

1. Draw a stepwise mechanism for the following reaction. Please use appropriate curved arrows to indicate the
movement of all electrons that moved during the reaction. Please do not omit any important steps (25 points.
Each intermediate structure worth 1 point; each curved arrow worth 1 point until 25 points are reached).

2. Draw a stepwise mechanism for the following reaction. Please use appropriate curved arrows to indicate the
movement of all electrons that moved during the reaction. Please do not omit any important steps (25 points.
Each intermediate structure worth 5 or 2 points; each curved arrow and other items worth 2 points until 25
points are reached).

CH2420, Organic Chemistry II, Exam Final

3:005:00 PM, April 23rd, 2012 (total 300 points)

Please print your name CLEARLY here:

Last,
TEST FORM

First
A

Make sure you have chosen the form of test that is different from those chosen by the students next to you.
There are three forms, A, B and C, which are printed on papers of different colors. The questions are the same
but they and the answers to them are arranged in different orders.
The exam has two parts. The first part contains 30 multiple choice questions. The total points for this part are
240 (8 30). Each question has only one correct answer. You need to mark your answers of these questions
with a pencil on your answer sheet. This part will be graded using a scanner. As a result, answers marked on the
exam will NOT be graded. In addition to answers, please also fill the following information on your answer
sheet: 1. your name; 2. I. D. number, print it in the form and then mark the corresponding numbers; 3. Test form
number, which is A for you.
The second part contains 3 questions that need you to provide stepwise mechanism of organic reactions. The
total points for this part are 60 (20 3). Answers to these questions need to be put in the space provided in the
exam. This part will be graded manually.
The total points you earned will be entered into WebCT. The keys will be posted in WebCT. I will send an
email to the class when ready. For grading policy, please see Syllabus.

Part 1: Multiple Choice Questions. (8 30 = 240 points)

1. What is the product of the following reaction sequence?

A) Compound A
B) Compound B
C) Compound C
D) Compound D
2. Identify the reactants required for the formation of an enamine.
A) A ketone or an aldehyde and a secondary amine
B) A ketone or an aldehyde and a primary amine
C) An ylide and a primary amine
D) An ylide and a secondary amine
3. What 10-carbon compound will undergo ozonolysis to give 2,4-pentadione as the only product?
A)
B)
C)
D)

1,2-Dimethylcyclopropene
1,6-Cyclodecadiene
1,2,4,5-Tetramethyl-1,4-cyclohexadiene
2,4-Dimethyl-1,4-cyclooctadiene

4. Determine the product of the following reaction.

Br

NH2

Br

A) Compound R
B) Compound S
C) Compound T
D) Compound U
5. Match 1H NMR spectra with compounds.

OH
O

OH

A) Spectrum E is from compound W, and spectrum F is from compound X

B) Spectrum E is from compound X, and spectrum F is from compound Y
C) Spectrum E is from compound X, and spectrum F is from compound Z
D) Spectrum E is from compound Z, and spectrum F is from compound X
6. Which reagent would be used to reduce the alkene in cyclopentenone?
A) NaBH4
B) LiAlH4
C) 1 equivalent H2 and catalytic amount of Pd/C
D) DIBAL-H

7. Which of the following molecules would give an IR spectrum with the following peaks: 1650 cm-1; 2900 cm1
; 3040 cm-1; 3300 cm-1 (weak); 3400 cm-1 (weak)

A)
B)
C)
D)

Compound W
Compound X
Compound Y
Compound Z

8. The structure below is -D-galactose.

Identify the hemiacetal carbon atom in this structure.

A) Carbon A
B) Carbon B
C) Carbon C
D) Carbons D and E
9. Select the product of the following reaction.

A) Compound A
B) Compound B
C) Compound C
D) Compound D
4

10. An unknown compound X has the molecular formula C6H14O. X shows a strong peak in its IR spectrum at
3000 cm1. The 1H NMR spectral data of X are given below. What is the most likely structure of X?
absorption
triplet
singlet
quartet
singlet

1.0
1.1
1.5
3.5

H ratio
3
6
2
3

A) Compound A
B) Compound B
C) Compound C
D) Compound D
11. Add reagents for the following multiple step synthesis.

A) W, X, Y and Z are CH3CH2COCl/AlCl3; Br2/FeBr3; Zn(Hg)/HCl; HNO3/H2SO4, respectively

B) W, X, Y and Z are CH3CH2COCl; Br2/FeBr3; Zn(Hg)/HCl; HNO3/H2SO4, respectively
C) W, X, Y and Z are CH3CH2COCl/AlCl3; Br2/heat; Zn(Hg)/HCl; HNO3/H2SO4, respectively
D) W, X, Y and Z are CH3CH2COCl/AlCl3; Br2/FeBr3; mCPBA; SO3/H2SO4, respectively
12. Which of the following alkenes undergo allylic bromination to form a single monobrominated product (not
including stereoisomers)?

A) Alkene A
B) Alkene B
C) Alkene C
D) Alkene D

13. Select the structure of the product in the following reaction.

A) Product A
B) Product B
C) Product C
D) Product D
14. Which of the following compounds give one singlet in 1H NMR spectra?
O
Cl

Cl
Br

Br

Br

Br

Br

O
Y

A) Compounds S, U, X, Z
B) Compounds T, V, X, Y
C) Compounds T, U, W, Z
D) Compounds S, U, W, Z
15. Which of the following reaction starting materials would yield the compound below?

CO2 Me
A.

CO2Me

B.

MeO2C

CO2Me

CO2Me
C.

CO2Me

D.

MeO2C

CO2Me

A) Starting materials A
B) Starting materials B
C) Starting materials C
D) Starting materials D
16. Which of the following compounds matches or match the IR spectrum shown?

OH
OH

O
O

A) U, X and Z
B) V, W and Y
C) Only U
D) Only X
17. Name the following compound.

A) 2,3-Dibromoaniline
B) 2-Bromo-5-aminobromobenzene
C) 2-Bromo-3-aminobromobenzene
D) m,o-Dibromonitrobenzene
18. Rank the following in terms of increasing reactivity for an SN1 reaction.

A) X<Y<Z
B) Z<Y<X
C) Z<X<Y
D) Z<Y=X
19. Which of the following reagents/conditions are appropriate to convert compound Y to compound Z?

A) First HBr, then PCC

B) First Br2/heat, then KOtBu
C) First mCPBA, then H2/Lindlar catalyst
D) First Br2/heat, then HBr
20. What is the first step in the general mechanism for electrophilic aromatic substitution?
A) Protonation of the aromatic ring
B) Deprotonation of the aromatic ring
C) Addition of the electrophile to the aromatic ring
D) Loss of the electrophile from the aromatic ring
8

21. Why is the nitro group a meta director?

A) Because it is sterically very large
B) Because it adds electron density to the meta position, thus activating it
C) Because it stabilizes the intermediate cation
D) Because it removes more electron density from the ortho and para positions than the meta position, thus
deactivating the meta position less
22. How could you separate the following compounds?

A) React with KMnO4

B) Make a weakly basic aqueous solution, then extract with an organic solvent
C) Make an acidic aqueous solution, then extract with an organic solvent
D) Hydrogenate
23. Assign carbon-13 NMR signals to each carbon in the compound shown.

A) C1, C2, C3 and C4 appear at 23, 70, 32 and 10 ppm, respectively

B) C1, C2, C3 and C4 appear at 70, 23, 32 and 10 ppm, respectively
C) C1, C2, C3 and C4 appear at 32, 70, 23 and 10 ppm, respectively
D) C1, C2, C3 and C4 appear at 10, 70, 32 and 23 ppm, respectively
24. Rank the following from most to least acidic.

A) Compound A > Compound B > Compound C

B) Compound B > Compound A > Compound C
C) Compound A > Compound C > Compound B
D) Compound B > Compound C > Compound A
25. What is the missing reagent in the reaction below?

A) Compound A
B) Compound B
C) Compound C
D) Compound D
26. What is the product of the following reaction?

A) Compound A
B) Compound B
C) Compound C
D) Compound D

10

27. Which reagent would bring about the following transformation?

A) LiAlH4
C) Br2, light
B) FeCl3
D) Basic KMnO4
28. What reagent(s) is (are) needed to add NO2 to benzene?
A) HNO3, HCl
B) HNO3, H2SO4
C) NO2(g)
D) NO2, CCl4
29. An electron donating group attached to a benzoic acid will:
A) Make the benzoic acid less acidic
B) Make the benzoic acid more acidic
C) Deactivate the benzene ring
D) Not change the acidity of the benzoic acid
30. Provide reagents for the following multistep synthesis.

A) Reagent X is Cl2 and water; reagent Y is NaH; reagent Z is first NaCCH, then water
B) Reagent X is first Cl2, then water; reagent Y is HCl; reagent Z is NaCCH and water
C) Reagent X is Cl2 and water; reagent Y is NaH; reagent Z is first water, then NaCCH
D) Reagent X is Cl2; reagent Y is NaH; reagent Z is first NaCCH, then water

11

Part 2: Mechanism of Organic Reactions. (20 3 = 60 points)

1. Draw stepwise mechanisms for all the following reactions that are used to synthesize the alkene product. Use
appropriate curved arrows to indicate the movement of all electrons that moved during the reaction. Please
do not omit any important steps (20 points. Each intermediate structure worth 3 points; each curved arrow
and other items worth 1 point until 20 points are reached).
O
CH2

Ph3P

+ CH3Br

Ph3PCH3

BuLi
Ph3P

CH2

Br

12

2. Draw a stepwise mechanism for the following reaction. Please use appropriate curved arrows to indicate the
movement of all electrons that moved during the reaction. Please do not omit any important steps (20 points.
Each intermediate structure worth 4 points; each curved arrow and other items worth 1 point until 20 points
are reached).

AlCl4
H3C

Cl

CH3 H

CH3 H

CH3 H
H3C

CH3

Cl

AlCl3

CH3

H3C

CH3

CH3 H
CH3

H
H

Cl
HCl

CH3

AlCl3

H3C

CH3

CH3 H
H3C

H3C

CH3

H
H

AlCl3

AlCl3

Total 20 points. Each structure in red worth 4 points; each curved arrow and structure
in green worth 1 point until 20 points are reached. You do not need to be completely
correct to get full points. Other correct drawings will also get points.

13

3. Draw a stepwise mechanism for the following reaction. Please use appropriate curved arrows to indicate the
movement of all electrons that moved during the reaction. Please do not omit any important steps (20 points.
Each intermediate structure and curved arrow worth 1 point until 20 points are reached).

H
Al

Al

AlH3

N
H

H
Al
O
AlH3

O
H
N

AlH3

H
O

Al

H
H

AlH3
H
H

Al

H
N

H
AlH3

OH
H

H
H
N
H

Total 20 points. Each curved arrow in green and each structure in red worth
1 point until 20 points are reached. You do not need to be completely correct
to get full points. Other reasonable drawings will also get points.

14