Final Exam for Organic II
200pts(Weighted as 300)
Name
Good luck all round!
1) Identify the class of compounds each of the following molecules belong
to (15pts).
R O H
O
R C H
O
R CN
R O R
O
R C NR2
O
R C O-R
H
N
C O
O
O
R C O C R
O
R C O-H
2) For each of the amides and amines state whether they are primary,
secondary or tertiary (4pts).
3) Circle one of the above compounds that is reactive enough to react with
neutral water (2pts).
4) Give two characteristic physical or chemical properties of aromatic
compounds (4pts).
Final Exam for Organic II
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5) Indicate which of the following molecules are aromatic, non-aromatic or
anti-aromatic. (Assume all the molecules are planar). (15pts)
O
H3C
H3C
CH3
CH3
H3C
CH3
H H
N+
+
O
NO2
S
N
N
N
+
NO2
6) Pick one of the above antiaromatic molecules, and use the polygon rule
to demonstrate its antiaromaticity. (8pts)
Final Exam for Organic II
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7) Give the products in six of the following reactions, paying attention to
regio/stereochemistry where applicable. (18pts)
heat
NC
CN
O CH2CH2CH3
Ph
C CH2
Br2, H2O
Excess HBr
KOH
A
B
Ph
Excess HI
OH
O
F
CO, HCl
CuCl, AlCl3
CN
O
heat
CH3
Br2, FeBr3
NHCOCH3
Final Exam for Organic II
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8) The below heterocycle contains two Nitrogen atoms, and is 6π Hückel
aromatic.
CH3
N
N
The lone pairs on the two Nitrogens play different roles in the aromaticity of
the molecule, and consequently one Nitrogen will get protonated before the
other.
Describe which one gets protonated first, and explain their differing basicity.
(10pts)
Final Exam for Organic II
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9) Give reagents and conditions to accomplish five of the following
transformations. (15pts)
CH3
CH3
O
CH2-OH
CH2-O-CH2
O2N
O2N
NO2
HO H
O
H3C
H3C
H
Ph Ph
Ph Ph
CH2CH3
CH3CH2
CH2CH2CH3
CO2H
CH2CH3
HO2C
O
CO2H
Br
A
O
CH2CH2CH3
(no marks for A)!!!
Final Exam for Organic II
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10) The addition of (1 equivalent of) HBr to cis-1,2-dimethyl-3,5cyclohexadiene generates a mixture of products.
H3C
H3C
HBr
mixture
Draw the products, predict their approximate ratio, and mechanistically
account for the mixture of products. (10pts)
Final Exam for Organic II
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11) Circle the stronger base in the following pairs, and in a sentence explain
your choice. (6pts)
(a)
O2N
NH2
NH2
O
(b)
F3C N
H
C
CH3
H3C N
H
H2
C
CF3
12) Circle the stronger acid in the following pairs, and in a sentence explain
your answer. (12pts)
(a)
O
H3C C OH
CO2H
CF3CH2 OH
CO2H
(b)
CN
O
(c)
O
Cl3C C OH
Br3C C OH
O
O
(d)
H C OH
H3C C OH
Final Exam for Organic II
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13) Name five of the following compounds in IUPAC acceptable terms.
(15pts)
O
O
O
O
O
O
Cl
O
NH
O
14)
O
Rank methanal (formaldehyde), propanone and propanal in
increasing reactivity with nucleophiles, and explain their differing
reactivities. (12pts)
Final Exam for Organic II
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15) Fill in the blanks for five of the following reactions. (25pts)
Br
1) excess Mg
?
?
(a)
Br
2) excess CO2
+
3) H3O
NH2
1) NaNO2, HCl
?
?
(b)
2) H3PO2, heat
CH2-OCH3
(c)
?
NaOCH3
?
CH2-OCH3
D
CH2CO2H
CH2CONH2
P2O5
?
(d)
CH2
CH2CN
O
C Ph
?
(e)
CH2CH2Ph
?
O
C Cl
(f)
?
?
SOCl2
O
C
?
Final Exam for Organic II
H
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16) Give the mechanism for one of the below conversions (10pts)
1) BuLi
S
H
S
H
O
2) CH3CH2Br
3) H3O+, HgCl2
CH3CH2
C
CH2CH3
or
CH3CH2CH2CH2Cl, AlCl3
Final Exam for Organic II
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17) Give the starting material and mechanism for one of the following
schemes. (19pts)
(a)
Cl2, KOH
NH2
H2O
O
(b)
O
Na, NH3
H
C2H5OH
H
(c)
1) CH3Br, Ph3P
2) BuLi
3) Warm
Ph
C CH2
Ph
Final Exam for Organic II
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*Bonus question* (1pt for within $5k, 2 pts within $1k)
What is the base rate 10 month salary (i.e. excluding summer compensation
and consultancy, etc) for an assistant chemistry professor at Rutgers?
Final Exam for Organic II
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