Average = 60
CHEM 3311-100 Fall 2007
Exam 2
Professor R. Hoenigman
High = 100
Low = 10
I pledge to uphold the CU Honor Code:
Signature______________________________________________
Name (printed)____________________________________________________
Last four digits of your student ID number_______________________________
Recitation TA_____________________________________________________
Recitation number, day, and time______________________________________
You have 1 hour to complete this exam.
No model kits or calculators allowed.
Periodic table and scratch paper are attached.
DO NOT TURN THIS PAGE UNTIL INSTRUCTED TO DO SO.
Recitation Sections:
#
111
151
191
113
193
112
152
192
153
Day
Monday
Monday
Monday
Tuesday
Tuesday
Wednesday
Wednesday
Wednesday
Thursday
Time
8 am
2 pm
5 pm
8 am
5 pm
8 am
11 am
5 pm
8 am
TA
Noel
Noel
Noel
Noel
Noel
Doug
Jon
Doug
Noel
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TOTAL________/100
CHEM 3311, Fall 2007
Exam 2, page 1 of 4
1. (10 pts) On Exam 1, you saw the structure of Bufotoxin (shown below). In the boxes below,
write the name of each indicated functional group. Spelling counts!
(2 pts each)
alkene
O
O
ester
CH3
amide
CH3
NH
CH3
O
OH
H
N
H2N
O
N
H
O
O
alcohol
O
O
OH
carboxylic
acid
2. (10 pts) Draw bond line structures for (E)-1-chloropropene, 1,1,-dichloro-2-methylpropene,
and (E)-2,3-dichloro-2-butene. Circle the alkene that has the greatest dipole moment. Draw a
box around the alkene that has the smallest dipole moment.
Book Problem 5.8
(2 pts each structure, 2 pts circle, 2 pts box)
Cl
Cl
Cl
Cl
Cl
CHEM 3311, Fall 2007
Exam 2, page 2 of 4
3. (11 pts) Fill in the organic product of the following reaction and, using arrows to show the
flow of electrons, draw a mechanism to account for its formation. Be sure to show the
appropriate stereochemistry of the product.
H3C
H3CH2C
Cl2
Cl
Cl
H
CH2CH3
H3C
H3CH2C
Cl
H3C
H3CH2C
Cl
CH2CH3
Cl
H
Cl
H
CH2CH3
Cl
Cl
4. (10 pts) Deuterium oxide (D2O) is water in which the protons (1H) have been replaced by
their heavier isotope deuterium (2H). When D2O is added to an alcohol (ROH), deuterium
replaces the proton of the hydroxyl group.
ROH
+ D2O
+
ROD
DOH
The reaction takes place extremely rapidly, and if D2O is present in excess, all the alcohol is
converted to ROD. This hydrogen-deuterium exchange can be catalyzed by either acids or
bases. If DO- is the catalyst in base, write a reasonable mechanism for the conversion of
ROH to ROD under basic conditions.
Book Problem 4.53
RO
H
RO
DOH
OD
ROD
DO
D
DO
CHEM 3311, Fall 2007
Exam 2, page 3 of 4
4. (24 pts) Draw the major organic product(s) for the following reactions. If necessary, clearly
show the stereochemistry of the products. If no reaction occurs, write NR.
(3 pts each)
A. Book Problem 5.14d
H2SO4
2,3,3-trimethyl-2-butanol
B. Book Problem 4.20c
2,2,4-trimethylpentane
Br
Br2
!
C. Book Problem 4.38c
Br
Br
HCl
OH
Cl
D.
Br
HBr
HOOH
E.
HO
(E)-3-ethyl-4-methyl-2-pentene
1) OsO4
OH
H
2) HOOH
H3C
F.
CH(CH3)2
CH2CH3
O
Cl
OOH
+
O
G.
2-bromobutane
KOC(CH3)3
H.
Cl
2,2-dimethylcyclopropanol
HCl
CHEM 3311, Fall 2007
Exam 2, page 4 of 4
5. (35 pts) Propose an efficient synthesis for each of the following transformations. You may
use any reagents you like.
A. Book Problem 6.36i (10 pts)
cyclopentyl iodide from cyclopentane
Br
Br2
h!
NaOMe
HI
I
B. (15 pts)
OH
from
methylcyclobutane
OH
Br
Br
Br2
h!
NaOMe
HBr
HOOH
t-BuOK
OH
H3O+
O
MCPBA
OH
C. Book Problem 6.36a (10 pts)
1-propanol from 2-propanol
OH
H2SO4
1) B2H6
2) HOOH, HO
OH