Name_____________________________________________________ Exam 1 R340 Fall 2014
This exam contains 104 points and will be scored out of a maximum of 100 points.
1. (8pts) Draw a bond-line formula for each of these molecules, then indicate whether you would
consider each of these atoms to be Lewis acidic or Lewis basic.
a. The carbonyl carbon atom of a cyclic ketone
b. The oxygen atom of a saturated alcohol
2. (14pts) On the structure below,
A. Label three functional groups on the structure below.
B. Indicate the hybridization of the heteroatoms on the structure below.
C. How many lone pairs in this molecule? __________
D. How many hydrogen atoms in this molecule? __________
3. (6pts) Circle the aromatic compound(s), and put an X through any that are not aromatic.
4. (14pts) Although there are 4 areas of electron density around the nitrogen atom in the Lewis dot
structure below, the nitrogen atom bond angles are 120o.
A. Draw a simplified orbital overlap picture for this molecule.
B. How does your picture help explain why the bond angles are 120o?
C. How many lone pairs are orthogonal to the pi system?__________
D. How many electrons are in the pi system? _____________
E. Is this molecule aromatic? _______________
5. (12pts) For each of these structures, draw all significant resonance structures. If there are no
significant resonance structures, write “no significant structures.” Blank answers are incorrect.
6. (6pts) Which of these aromatic systems is “electron rich” compared to benzene? Circle it, and draw
one resonance structure that shows an electron rich benzene ring.
7. (12pts) Indicate which of the following lone pairs is more stable, and circle the physical reason it is
more stable.
8. (8pts) Draw bond-line structures of both enantiomers of 2,3,6-trimethylhept-4-yn-2-ol . Use
appropriate bond angles in your bond-line formula.
9. (8pts) Draw dipole arrows designating any polar bonds in these molecules. Indicate any carbon
atoms that are Lewis acidic.
10. (8 pts) Fill in the boxes:
11. (8pts) For the following molecule, fill in the boxes as E/Z/R/S or put an “X” in the box if none of the
labels are appropriate.
PERIODIC TABLE OF THE ELEMENTS
1
H
1.008
3
Li
6.941
11
Na
22.99
19
K
39.10
37
Rb
85.47
55
Cs
132.9
87
Fr
(223)
4
Be
9.012
12
Mg
24.31
20
Ca
40.08
38
Sr
87.62
56
Ba
137.3
88
Ra
(226)
Scratch work:
1
Atomic Number
H
Symbol
1.008 Atomic Weight
5
B
10.81
13
Al
26.98
21
22
23
24
25
26
27
28
29
30
31
Sc
Ti
V
Cr
Mn
Fe
Co
Ni
Cu
Zn
Ga
44.96 47.88 50.94 52.00 54.94 55.85 58.93 58.69 63.55 65.39 69.72
39
40
41
42
43
44
45
46
47
48
49
Y
Zr
Nb
Mo
Tc
Ru
Rh
Pd
Ag
Cd
In
88.91 91.22 92.91 95.94 (98) 101.1 102.9 106.4 107.9 112.4 114.8
57
72
73
74
75
76
77
78
79
80
81
La
Hf
Ta
W
Re
Os
Ir
Pt
Au
Hg
Tl
138.9 178.5 180.9 183.9 186.2 190.2 192.2 195.1 197.0 200.6 204.4
89
Ac
(227)
6
C
12.01
14
Si
28.09
32
Ge
72.61
50
Sn
118.7
82
Pb
207.2
7
N
14.01
15
P
30.97
33
As
74.92
51
Sb
121.8
83
Bi
209.0
8
O
16.00
16
S
32.07
34
Se
78.96
52
Te
127.6
84
Po
(209)
58
Ce
140.1
90
Th
232.0
69
Tm
168.9
101
Md
70
Yb
173.0
102
No
71
Lu
175.0
103
Lr
59
Pr
140.9
91
Pa
(231)
60
Nd
144.2
92
U
238.0
61
Pm
(145)
93
Np
62
Sm
150.4
94
Pu
63
Eu
152.0
95
Am
64
Gd
157.3
96
Cm
65
Tb
158.9
97
Bk
66
Dy
162.5
98
Cf
67
Ho
164.9
99
Es
68
Er
167.3
100
Fm
9
F
19.00
17
Cl
35.45
35
Br
79.90
53
I
126.9
85
At
(210)
2
He
4.003
10
Ne
20.18
18
Ar
39.95
36
Kr
83.80
54
Xe
131.3
86
Rn
(222)