Sp 2008 Final Organic II
200pts (Weighted as 300)
Name
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) Circle a molecule in (2) with an sp2 hybridized Nitrogen atom. (1.5pts)
4) Put a cross through a compound in (1) which has ring strain (1.5pts).
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5) Identify the general class of each of the below reactions (e.g. oxidation,
electrophilic addition, etc) (16pts)
H
OH
H2SO4
(a)
O
(b)
-
R
Cl
CH3NH2, H+
O
(c)
OH
R
R
O
R
OH
N-CH3
R
R
CH3O(d)
OCH3
F
PCC
(e)
CH2OH
O
(f)
R
R
CHO
NaBH4
OH
R
R
H
NO2
HNO3
(g)
O
(h)
R
R
HCN
OH
R
R
CN
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6) Define the following terms (10.5pts).
CONCERTED REACTION
PERICYCLIC REACTION
THERMODYNAMIC PRODUCT
7) Give one use of Molecular Orbital theory, and also state a disadvantage
of MO theory. (4pts).
8) State whether each of the following Molecular orbitals are overall
bonding, antibonding or nonbonding (4.5pts).
(a)
(b)
(c)
9) Draw two Lewis resonance structures for a carboxylate anion RCO2(4pts).
10) Which one is more stable (2pts)?
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11) Indicate which of the following molecules are aromatic, non-aromatic or
anti-aromatic. (Assume all the molecules are planar). (15pts)
CH3
P
H H
N+
N
Mg-Br
O
O
+
12) Circle the more stable species in these pairs. (8pts)
a)
b)
c)
O
d)
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13) Give the products in six of the following reactions, paying attention to
regio/stereochemistry where applicable. (18pts)
Excess HI
Ph
O
O
F
CH3Cl, AlCl3
NO2
1) Zn, HCl
2) NaNO2, HCl
3) CuCl, HCl
CH3
Br2, uv light
heat
H
Br
CF3
1) NaOH
OH
2) CH3CH2CH2-Br
Ph
C CH2
Cl2, H2O
KOH
A
B
Ph
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14) 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 (1.5pts)
What is the hybridization of the Nitrogen atom (1.5pts)
15) Write the mechanism for the electrophilic aromatic substitution reaction
below. (8pts)
NO2
NO2+ HSO4-
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16) Give reagents and conditions to accomplish five of the following
transformations. (15pts)
NO2
Br
O2N
O2N
O
N
O
N
CHO
CO2H
OH
O
H
H
NO2
Cl
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17) Circle the stronger base in the following threesomes. (10pts)
H
N
H
N
CH3
N
(a)
CH3
N
CH3
(b)
(c)
NH2
O
(d)
(e)
NH2
NH
N
O
N
H
N
H
O
HCl
H2O
NH2
O
H
N
O
O
HF
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
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19) Name the following compounds in IUPAC form (14pts).
O
(CH3CH2)4N+ F-
H3C
Br
CH3
O
CH3
O
NH2
HO
20) Fill in the blanks for two of the following reactions. (6pts)
(a)
CH3CH2 NH2
O
(b)
(c)
H3C C CH3
NH2
HCl
Ag2O
1) excess CH3-Br
2) Ag2O, H2O, heat
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21) Give reagents for the following transformations. (9pts)
Ph
Ph
O
N
N
O
O
N
CF2H
H
H
H
O
OH
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22) Give the mechanism for two of the below conversions. (16pts)
1) excess CH3Br
NH2
(a)
2) Ag2O, H2O, heat
NH2
(b)
+
N N
NaNO2, HCl
Cl-
O
(c)
H3C
HOCH2CH2OH
Ph
H2SO4
O
H3C
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*Bonus question* (up to 4 points)
Give four different ways that knowledge of organic chemistry could help
you make money.
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