Course
: CHEM 202 (Organic Chemistry II)
Section
:A
Instructor
: Dr. Bassam Alameddine
Date
: 4/12/2007
Student Name _______________________________
Instructions
I.D.___________________
For Instructor’s Use Only
 Time allowed: 1 hr 30 min.
Question
Question
 Cheating in any way, form or Question
method will be rewarded with an Question
F grade
Question
Question
 Read each question carefully
before answering
I
II
III
IV
V
VI
 Solve the questions that you are
confident about their answers Total
Grade
first
This booklet consists of 11 pages including this page
/100
CH202 Exam#2
2
Fall 07/08
I.a Circle the compound below which is the strongest acid.
i. CHCl2CH2CH2COOH
ii. ClCH2CHClCH2COOH
iii. CH3CCl2CH2COOH
iv. CH3CHClCHClCOOH
v. CH3CH2CCl2COOH
I.b Explain your answer above using structures and words.
II. Compare each pair of compounds and circle the compound that
contains the MOST acidic proton.
(a)
(b)
CF3COOH
CH3COOH
CH3COOCH3
(c)
H2O
(d)
OH
O
O
H3C
O
CH3OH
III. Fill in the missing reagents or major organic products for each of the
following reaction sequences.
a)
O
H+
HO
OH
Heat
CH202 Exam#2
Fall 07/08
b)
O
Cl
LiAlH(o-t-Bu)3
OMe
c)
OH
CH2OH
Excess PCC
d)
CH3
O
H2O
H3C
CH3
Cl
e)
O
O
O
H2NCH3
f)
O
OH
1) SOCl2
2) AlCl3
3
CH202 Exam#2
Fall 07/08
g)
O
O
H+
OH
+
Cl
CH3
h)
O
H
1) Na+ C CCH3
2) H+
i)
MgBr
1)
O
2) H+
O
O
j)
O
1.CH3CH2MgBr
2. H3O+
4
CH202 Exam#2
5
Fall 07/08
IV. The syntheses below can be accomplished in two or three synthetic
steps to give the product indicated. Give a plausible intermediate
compound and then the reagents that will accomplish each step.
.
i)
O
O
H
ii)
N
CH202 Exam#2
6
Fall 07/08
V. Prepare the following products:
i) Malonic acid (propandioic acid) from acetic acid
ii) Ethyl 2-methylbutanoate from ethanol
VI. Draw the mechanism for the transformation of the acetal given below.
Use correct arrow notation and show all proton transfer steps. Identify the
intermediate hemiacetal compound formed.
H+, CH3OH
HO
O
OCH3
O
CH3
CH202 Exam#2
7
Fall 07/08
VII. Write structures for the compounds A through D.
CH2COOC2H5
Mg
A
1. Acetone
2.
Br
B
H2O
H3O+
C H2/Pt
heat
VIII. Complete the roadmap below. Supply
intermediates, starting materials, and products.
all
missing
reagents,
O
CH2CH2COH
HCN
LiAlH(0-t-Bu)
O
CH2CH2CH
PCC
H2O
Br
1.
2. H+
MgBr
1. N2H4
2. Base, heat
D
CH202 Exam#2
8
Fall 07/08
IX. Assign the 1H NMR spectra to either compound A or compound B.
Provide a brief explanation for each of your assignments.
O
H3C
H3C
CH3
CH
O
O
CH
C
CH3
OCH3
F
A
B
16
s, 3H
15
3.81
14
s, 3H
13
2.06
12
d, 3H
11
t, 1H
10
d, 1H d, 1H s, 1H
1.30
1.32
6.65
7.32
9
4
6.80
6.82
6.87
8
3
7
2
6
1
5
0
7.30
7.34
6.80
6.79
7.30
7.34
7.40
6.87
7.30
7.20
7.10
7.00
6.90
6.80
6.70
6.60
4
3
2
7.32
7.34
q, 1H
6.65
7.30 6.82
6.87
3.70
1
0
3.72
3.67
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
CH202 Exam#2
9
Fall 07/08
13.0
12.5
12.0
11.5
2.02
11.0
q, 1H d, 1H
10.5
10.0
4.5
7.10
7.10
4.0
7.10
t, 1H d, 1H
6.88
7.22
7.23
7.23
3.5
8.5
3.0
8.0
2.5
7.5
2.0
7.0
1.5
6.5
1.0
7.21
7.24
7.24
7.24
7.25
7.25
7.08
7.08
7.10
7.11
d, 3H
6.76
6.78
9.5
9.0
s, 3H
6.88
6.78
6.78
6.88
6.90
7.08
7.21
7.20
6.76
6.76
6.86
6.86
6.86
6.90
6.90
6.76
7.08
1.50
1.51
0.5
6.0
0.0
5.5
7.20
7.10
7.00
6.90
6.80
6.70
5.0
4.5
4.0
3.5
3.0
q, 1H
2.5
2.0
6.78
7.10
6.88
5.90
5.92
1.5
1.0
5.94
5.89
0.5
0.0
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
Good Luck
Dr. Bassam Alameddine
CH202 Exam#2
Fall 07/08
10
CH202 Exam#2
Fall 07/08
11