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CHEMISTRY 231

EXAM I

Summer 2008 (6/2/08)
Professor Thomas Greenbowe
Mr. Jacob Schroeder



Page Points Score

2

3

4

5

6

19 pts

21 pts

28 pts

20 pts

12 pts


________

________

________

________


Total 100 pts ________



2

1. (5 pts)

a) Circle the atom in each of the following bonds that carries the partial positive charge.

a. N–S b. Si–I c. N–Br d. C–Cl

b) Which of the bonds in part a) is the most polar?


2. (6 pts) The Lewis structure for carbonic acid (formed when CO
2
dissolves in water) is usually given as

H O C O
O
H


What is wrong with the following structures? Explain.


a. H O C O
O
H b. H O C O
O
H c. H O C O
O
H









3. (4 pts) Are the following Lewis structures considered to be resonance structures? Explain. How can
you predict which is the more likely structure for POCl
3
?

P
Cl
Cl
Cl
O O
Cl
Cl
Cl
P






4. (4 pts) The organic molecule ketene, C
2
H
2
O, has the following Lewis structure: C
H
H
C O
How many sigma bonds are in this molecule? _____

How many pi bonds are in this molecule? _____

3

5. (6 pts) Acetic acid (F.W. = 92.0 g/mol) reacts with isopentyl alcohol (F.W. = 88.1 g/mol) to yield
isopentyl acetate (F.W. = 130.1), a fragrant substance with the odor of bananas. If the yield from the
reaction of acetic acid with isopentyl alcohol is 45%, how many grams of isopentyl acetate are formed
from 3.58 g of acetic acid and 4.75 g of isopentyl alcohol? The reaction is:

CH
3
CO
2
H + C
5
H
12
O ! C
7
H
14
O
2
+ H
2
O
Acetic acid isopentyl isopentyl
alcohol acetate









6. (3 pts) Complete and balance the following reaction. Use curved arrows to show the movement of
electron pairs.

C
H
H
H
_
+ H O
H
A B
+



7. (6 pts) Draw a Lewis structure for each of the following species. Be sure to indicate all lone electron
pairs and formal charges where appropriate.

a. HNO
3
b. NO
2






c. [CH
3
NH
3
]
+






8. (6 pts) Give the correct name and draw a skeletal structure for the following structures:

a.
CH
3
CH
2
CHCH
2
CHCH
3
CH
3
CH
3
b.
C C
H
H
CH
2
CH
3
CH
3




4

9. (16 pts) Refer to the following structures to complete the table below.

C
CH
3
O
CH
3
1
NH
3
2
C N H
3
CH
3
CH
2
CH
2
CH(CH
3
)
2
4


Carbon (1) Nitrogen (2) Carbon (3) Carbon (4)
Regions of
electron density

Molecular
geometry

Bond angle

Hybridization



10. (6 pts) How many different molecules have the formula C
5
H
12
? Draw the Lewis structures.














11. (6 pts) Draw a correct Lewis structure for the following formulas:

a. 3-ethyl-2-methylhexane b. cis-4-methyl-2-hexene




c. tert-butylchloride



5

12. (4 pts) Draw the most stable 3-D conformation of cis-1,3-diethylcyclohexane.







13. (6 pts) Match the compounds below with the following terms: hydrocarbon, aldehyde, amine,
carboxylic acid, alcohol, ketone.
CH
3
CH
2
C
O
OH
CH
3
CCH
2
CH
3
O

CH
3
CH
2
CHCH
3
OH
CH
3
CH
2
C
O
H

N
H
CH
2
CH
3
CH
3
CH
3
CH
2
CHCH
3
CH
3



14. (4 pts) Determine whether the following pairs of structures are actually different compounds or simply
resonance forms of the same compound.

a.
O O
b.
CH
2
C
O
H
C
O
H CH
2










15. (6 pts) Give an acceptable IUPAC name for each skeletal structure below.

a. b.



6

16. (6 pts) Which of the following Lewis structures represent the same compound? Which ones represent
different ones?

a.

H
3
C
CH
3
H
CH
3
CH
3
H
H
CH
3
H
H
CH
3
H
CH
3
H
CH
3
H




b.





c.

CH
3
CH
3
H
H
H
H
CH
3
CH
3
H
CH
3
CH
3
H






17. (6 pts) The structure of tert-butylcyclohexane is shown below.

H
C(CH
3
)
3

a. Draw the hydrogen and the tert-butyl group after undergoing a ring flip.

b. Circle the structure that would be the most stable of the two. Explain your choice.

7

Increasing electronegativity

1A 8A
H

2.1


2A


3A


4A


5A


6A


7A

Li

1.0
Be

1.5
B

2.0
C

2.5
N

3.0
O

3.5
F

4.0

Na

0.9
Mg

1.2


3B


4B


5B


6B


7B


(------8B------)


1B


2B
Al

1.5
Si

1.8
P

2.1
S

2.5
Cl

3.0

K

0.8
Ca

1.0
Sc

1.3
Ti

1.5
V

1.6
Cr

1.6
Mn

1.5
Fe

1.8
Co

1.9
Ni

1.9
Cu

1.9
Zn

1.6
Ga

1.6
Ge

1.8
As

2.0
Se

2.4
Br

2.8

Rb

0.8
Sr

1.0
Y

1.2
Zr

1.4
Nb

1.6
Mo

1.8
Tc

1.9
Ru

2.2
Rh

2.2
Pd

2.2
Ag

1.9
Cd

1.7
In

1.7
Sn

1.8
Sb

1.9
Te

2.1
I

2.5

Cs

0.7
Ba

0.9
La-Lu

1.0-1.2
Hf

1.3
Ta

1.5
W

1.7
Re

1.9
Os

2.2
Ir

2.2
Pt

2.2
Au

2.4
Hg

1.9
Tl

1.8
Pb

1.9
Bi

1.9
Po

2.0
At

2.2

I
n
c
r
e
a
s
i
n
g

e
l
e
c
t
r
o
n
e
g
a
t
i
v
i
t
y

Fr

0.7
Ra

0.9


Periodic Table of the Elements
103
Lr
(260)
102
No
(259)
101
Md
(258)
100
Fm
(257)
99
Es
(252)
98
Cf
(251)
97
Bk
(247)
96
Cm
(247)
95
Am
(243)
94
Pu
(244)
93
Np
(237)
92
U
238
91
Pa
231
90
Th
232
71
Lu
175
70
Yb
173
69
Tm
169
68
Er
167
67
Ho
165
66
Dy
162
65
Tb
159
64
Gd
157
63
Eu
152
62
Sm
150
61
Pm
(145)
60
Nd
144
59
Pr
141
58
Ce
140
8A
18
7A
17
6A
16
5A
15
4A
14
3A
13
Lanthanides
Actinides
109
Mt
(266)
108
Hs
(265)
107
Bh
(262)
106
Sg
(263)
105
Db
(262)
104
Rf
(261)
89
Ac
227
88
Ra
226
87
Fr
(223)
83
Bi
209
82
Pb
207
81
Tl
204
80
Hg
201
79
Au
197
78
Pt
195
77
Ir
192
76
Os
190
75
Re
186
74
W
184
73
Ta
181
72
Hf
178
57
La
139
56
Ba
137
55
Cs
133
51
Sb
122
50
Sn
119
49
In
115
48
Cd
112
47
Ag
108
46
Pd
106
45
Rh
103
44
Ru
101
43
Tc
(98)
42
Mo
95.9
41
Nb
92.9
40
Zr
91.2
39
Y
88.9
38
Sr
87.6
37
Rb
85.5
86
Rn
(222)
85
At
(210)
84
Po
(209)
52
Te
128
53
I
127
54
Xe
131
36
Kr
83.8
35
Br
79.9
34
Se
79.0
33
As
74.9
32
Ge
72.6
31
Ga
69.7
30
Zn
65.4
29
Cu
63.5
28
Ni
58.7
27
Co
58.9
26
Fe
55.8
25
Mn
54.9
24
Cr
52.0
23
V
50.9
22
Ti
47.9
21
Sc
45.0
20
Ca
40.1
19
K
39.1
18
Ar
39.9
17
Cl
35.5
16
S
32.1
15
P
31.0
14
Si
28.1
13
Al
27.0
2
He
4.00
10
Ne
20.2
9
F
19.0
8
O
16.0
7
N
14.0
6
C
12.0
5
B
10.8
8B
2B
12
1B
11
10 9 8
7B
7
6B
6
5B
5
4B
4
3B
3
12
Mg
24.3
11
Na
23.0
4
Be
9.01
3
Li
6.94
2A
2
1A
1
1
H
1.01
110
Ds
(281)

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