Fall 09 Organic I Final Exam
200pts (graded as 300pts)
Name
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1) (10pts) Give one definition of an Acid
b) Without using profanity, what is “Organic Chemistry”?
c) What is the difference between structural isomers and stereoisomers?
d) Provide an example of each type of the above isomers.
2) Briefly explain what is meant the following terms:(16pts)
Electronegativity
Chiral Molecule
Concerted Process
Rate Determining Step
Syn Addition
Markovnikov Addition
Mechanism
π Bond
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3) Name the classes of compound that the following molecules belong to (E.g. alkane,
amide, etc). (15pts)
O
R
R
O-O-H
R O-R
R O-O-R
O
R
R
R O-H
O
H
R
O
O-H
R
O-R
O
R S-H
R
R
4) (16pts) For the below molecule, calculate the number of…
O
H
N
O CH3
a) carbon atoms
b) hydrogen atoms
c) oxygen atoms
d) π bonds
e) sp2 hybridized carbons
f) sp2 hybridized atoms
g) sp3 hybridized atoms
h) lone pairs (non bonding pairs) of electrons
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5) (4pts) What is meant by the term Hydrocarbon ?
(ii) What is a free radical ?
6) (12pts): For the below energy level diagram…
a) is this reaction exothermic or endothermic ?
b) Will the Equilibrium constant (K) be greater or less than 1.00 ?
c) how many transition states are there ?
d) how many steps is this multistep reaction ?
e) which step is the rate determining step ?
f) which is the fastest step ?
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7) Explain (including curly arrows) why in this electrophilic addition reaction, none of
product A is generated, and product B is formed exclusively. (8pts)
H CH3
CH3
H
Cl H
X
H-Cl
H
CH3
H
CH3
Product A
H-Cl
H CH3
CH3
H
H Cl
Product B
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8) Name the following molecules in IUPAC form. (16pts)
(a)
Cl
(b)
F
(c)
F
(d)
Br
OH
(e)
I
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9) Asterix (star, *) the chiral atoms in these molecules, and assign R or S to each chiral
center. (13pts)
F
(a)
Cl
F
CH3
Br
(b)
Br
H
CF3
(c)
(d)
Cl
H
H
Cl
Cl
Cl
CF2H
H
H
CF2H
10) Which of the above molecules are achiral, and in a sentence explain what makes
them achiral. (3pts)
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11) Circle the more stable member of each pair, and in a sentence explain your choice.
(10pts)
_
HO
(a)
_
H2N
_
CH3CH2O
(b)
_
CFH2CH2O
+
(c)
(d)
+
_
CH2
_
+
(e)
+
12) Circle the most stable member of each threesome (12pts)
OH
(a)
OH
OH
F
(b)
Cl
Cl
Br
F
Cl
Br
Br
H
H
H
H
H
Br
(c)
F
Br
Br
H
H
H
H
Br
Br
H
H
H
H
Br
H
H
CH3
(d)
Br
CH3
Br
Br
CH3
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13) Provide a mechanistic explanation for the observed mixture of products in the
following E1 reaction. (10pts)
CH3
CH3
NaOCH3
H3C
Br
CH3
H3C
CH3
H3C
CH3
E1
CH3
H3C
CH3
CH2
14) How many axial positions are occupied by Hydrogen atoms in the lowest energy
conformation of the below molecule? (5pts)
Br
Br
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15) Give the products of 5 of the 6 following reactions. (15pts)
(a)
excess I2
CH3CH2
CH3
1) Mg, Ether
(b)
I
OsO4, H2O2
(c)
(d)
H3C
H
1) BH3.THF
H3C
H
2) H2O2, NaOH
Br2
(e)
(f)
2) H2C=O
3) H3O+
1) Na, NH3
Ph
Ph
15b) Write the mechanism for one of the preceding reactions. (10pts)
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16) Give reagents to perform 5 of the 6 following transformations. (15pts)
(a)
OH
(b)
OH
(c)
H3C
(d)
O
H
CH3
OH
(e)
(f)
O
H3C
H
OCH3
Br
H
O
H
CH3CH2
H
16b) Write the mechanism for one of the preceding reactions. (10pts)
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