CHE 232-1, Spring 2008
Dr. Harris
Name (please print)___________________________________
Student ID #______________________________________
Short Answer (20 pts, 2pts. each)
1) Which of the following alkanes will give more than one monochlorination
product when treated with chlorine and light?
a) 2,2’-dimethylpropane, b) cyclopropnae, c) ethane, d) 2,3-dimethylbutane
2) Which type of halogenation is most selective?
3) Which of the following absorbs at the highest frequency?
a) 1,3,5-hexatriene, b) 1,3,5,7-octatetraene, c) 1,7-diphenyl-1,3,5-heptatiene,
d) 1,6-diphenyl-1,3,5-heptatriene
4) Draw 3,5-difluoroanisole.
5) Circle each of the following compounds that is aromatic.
6) Which of the following compounds will undergo fredal-Crafts alkylation?
a) benzoic acid, b) nitrobenzene, c) aniline, d) toluene
7) Which of the following compounds is most acidic?
O
O
OH
OH
O2N
H2N
O
O
OH
OH
8) Which of the following gives a secondary alcohol when treated with methyl
grignard?
a. butyl formate, b) 3-pentanone, c)pentanal, d) methyl butanoate
9) Draw N-ethyl-N-propylformamide.
10) What does a positive iodoform test tell you is present?
Predict the Products.-Show stereochemistry (20 pts., 2 pts. each)
11)
O
O
Cl
NaOH
O
H2O
O
12)
O
O
H3O+
O
H2O
O
13)
O
NaBH4, MeOH
O
OH H+, H O, heat
2
14)
O
I2
NaOH
15)
O
Br2
aq. NaOH
16)
O
HCl
H2O
17)
NaOH
O
O
heat
18)
O
O
NaOCH2CH3
+
O
H+, H2O, heat
O
19)
O
O
NaOCH2CH3
OCH3
H3 O+
20)
O
O
O
NaOCH2CH3
+
H3CO
OCH3
CH3CH2OH
Fill in the missing parts of this synthesis. (20 pts., 2 pts. each)
21)
O
B
O
O
NaOCH2CH3
OCH2CH3
CHCCH2Br
A
TsOH
HOCH2CH2OH
O
C
D
O
E
NaOH
CH3I
H3O+
F
22)
O
A
B
Li2CO3
Br2
LiBr
DMF
CH3COOH
NaOCH2CH3
H2 O
O
O
OCH2CH3
O
C
D
O
Mechanism: (Show and label all steps) (20 pts.)
23)
O
O
O
1) NaOEt, EtOH
+
OCH2CH3
2) H+, H2O, heat
O
O
Spectroscopy: Give the formula and structure. Circle your final answers.
(20 pts.)
24)
Exam Score
1-10 _________ (/20)
11-20_________ (/20)
21-22 ________ (/20)
22
_________ (/20)
23
_________ (/20)
Total________ (/100)