Sp 2011 Final
Organic II
200pts (Weighted as 300)
NAME:
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1) Identify the class of compounds that the following molecules belong to
(12pts).
R C NH2
O
R C H
O
R O H
R C R
O
R O O R
R C Cl
O
O
R C O-R
O
2) Draw a Lewis structure including lone pairs for the following similar but
different species: (12pts)
Nitronium Ion NO2+
Nitrosonium Ion NO+
Nitric Acid HONO2
Nitrous Acid HONO
3) What is an YLID ? (3pts).
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4) Identify each of the below reactions either as a substitution, addition,
elimination or condensation. (16pts)
NO2
(a)
O
(b)
OH
R
R
R
R
CN
(c)
OCH3
F
(d)
CH2OH
CHO
OH
O
(e)
R
R
R
R
H
O
(f)
(g)
(h)
R
OH
R
R
O
O
R
Cl
R
OH
N-CH3
O
R
R
OH
R
R
R
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5) Define the following terms (9pts).
CONCERTED REACTION
PERICYCLIC REACTION
THERMODYNAMIC PRODUCT
6) Give two uses of Molecular Orbital theory. (4pts).
7) State whether each of the following Molecular orbitals are overall
bonding, antibonding or nonbonding (6pts).
(a)
(b)
(c)
8) Draw two resonance structures for a carboxylate anion RCO2- (4pts).
9) Give two properties of a Protecting Group. (2pts)
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10) Indicate which of the following molecules are aromatic, non-aromatic or
anti-aromatic. (Assume all the molecules are planar). (15pts)
H
H
N
+
CH3
O
+
S
H3C CO2H
CH3
Al
11) Circle the more stable species in these pairs. (8pts)
a)
b)
c)
O
d)
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12) Give the products formed in five of the following reactions and cross out
the transformation you do not wish me to grade. (15pts)
(a)
O
Ph C CH3
1)Ph3P, CH3CH2CH2-Br
2) BuLi
3) warm
NH2
H-F
(b)
NH2
1) excess CH3I
(c)
2) Ag2O, H2O, heat
NH2
excess CH3CH2-I
(d)
1) NaCN
OTos
(e)
2) LiAlH4, H2O
(f)
O
H3C C CH3
1) PhCH2MgBr
2) H3O+
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13) The below heterocycle is pyridine, and it is 6π Hückel aromatic.
N
Explain why there are 6 π electrons (2pts)
What is the hybridization of the 5 carbons in the ring (2pts)
What is the hybridization of the Nitrogen atom (2pts)
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14) Explain briefly why each of the following attempted reactions are
fundamentally flawed, and will not work. (10pts)
NO2
Friedal Craft
Acylation
NO REACTION
O2N
KMnO4
2+2 Thermal
Cycloaddition
NO REACTION
NO REACTION
Nucleophilic Aromatic
Substitution
NO REACTION
CF3
Diels-Alder
NO REACTION
CF3
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15) Give reagents to accomplish five of the following transformations, and
cross out the transformation you do not wish me to grade. (15pts)
SO3H
Br
O
CO2H
O
O
O
H2N
O2N
H
N
Ph
CHO
CO2H
NO2
Cl
O
O
H
OH
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16) Circle the strongest base in the following threesomes. (10pts)
H
N
H
N
CH3
N
(a)
CH3
N
CH3
(b)
(c)
NH2
NH2
O
(d)
(e)
NH2
NH
N
O
N
H
O
HCl
H 2O
N
H
O
H
N
O
O
HF
17) Name the following compounds in IUPAC form (15pts).
Br
O
O
O
Cl
O
O
O
N
Sp11org2final.doc
H
O
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18) Circle the stronger acid in the following pairs. (8pts)
O
(a)
(b)
H3C C OH
O
F3C C OH
CO2H
(c)
Cl
(d)
O
HO S OH
O
CH3CH2 OH
O
Br3C C OH
CO2H
Cl
Cl
O
H C OH
19) What two products are formed when an acid chloride is hydrolyzed by
water ?
Write the mechanism for this reaction. (2+4pts)
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20) Give reagents for the following transformations. (8pts)
O
O
O
OH
OH
H
Ph
Ph
N
N
O
N
CF3
H
H
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21) Give the mechanism for one of the below conversions. (16pts)
O
(a)
H3C
HOCH2CH2OH
Ph
H2SO4
(b)
NH2
O
H3C
NaNO 2, HCl
O
Ph
+
N N
Cl-
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*Bonus question* (up to 4 points)
Draw a picture which describes your Organic chemistry experience at
Rutgers, Camden.
Sp11org2final.doc
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