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CH 310M/318M
TTh 8:009:30 a.m. (053750)
Spring 2007 Dr. Brian M. Bocknack

UTEID:

Midterm Exam #1
Thursday, February 15, 2007 7:009:00 p.m.
Do not open this exam booklet until you are told to do so! This exam is closed book, meaning no books, notes, calculators, or molecular models are allowed. Answers to the Part I multiple choice questions (Pages 28) must be submitted on the bubble sheet provided!!! Only answers marked on this bubble sheet will be graded!!! o You must use a #2 pencil to fill out the bubble sheet. o Please bubble in your name. If your entire name does not fit, it is only necessary to fill in the first 13 letters of your last name, and the first 5 letters of your first name. o Please sign your name in space labeled Signature. The unique number is 053750. o IMPORTANT!!! Bubble in your UTEID in the Identification field to the right of your name. o IMPORTANT!!! Bubble in the code 053750 in the Special Codes field. o Please leave the Birthdate, Sex, and Grade or Educ fields blank. Part I is not eligible for regrades. Once exams are graded, the answers you submit on the bubble sheet and your raw score for Part I will be posted in the Blackboard gradebook. Answers to Part II questions written in pencil are not eligible for regrades. Part II answers written in pencil with ink overlay will not be graded. If you do use a pen to answer Part II questions, only blue or black ink is acceptable. Part II answers written in red ink will not be graded. Be prepared to show your valid UT ID card to a proctor when attendance is taken, and also when you turn in your exam. You may not leave the exam room for any reason until you turn in your exam. Once you turn in your exam and leave the exam room, you will not be allowed to return!!! Page Page 9 (35)

10
ALL ANSWERS ON BUBBLE SHEET!!! CHECK BLACKBOARD!

(42)

28 Part I Total

11 Part II Total

(40)

(183)

(117)

Including this cover page, 2 blank pages (scratch paper), and the last page, which contains a periodic table, this exam contains 14 pages. Please feel free to tear off the scratch paper and the periodic table to use as you work through the exam.

DO ALL QUESTIONS!!!

BEST OF LUCK!!!

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Part I All answers to questions on this page must be submitted on the bubble sheet, using a #2 pencil. Only answers submitted on the bubble sheet will be graded!!! PLEASE READ EACH QUESTION VERY CAREFULLY!!!
To answer Questions 1 through 4, you will probably find it helpful to draw a Lewis structure for the molecular formula CCl3 . Space is provided below for you to draw your Lewis structure, but only the answers to the questions relating to this structure will be graded!

CCl3
1. (2 points) What is the total number of valence electrons that should be shown explicitly as bonding pairs and/or lone pairs in the correct Lewis structure for CCl3 ? A. 22 B. 23 C. 24 D. 25 E. 26

2. (4 points) What is the total number of electron groups surrounding the central carbon atom in the correct Lewis structure for CCl3 ? Use the definition of electron group that we discussed when we talked about VSEPR theory! A. 2 B. 3 C. 4

3. (4 points) What is the geometrical arrangement of electron groups surrounding the central carbon atom in the correct Lewis structure for CCl3 ? A. Trigonal planar B. Tetrahedral C. Linear

4. (4 points) Is this molecule polar or nonpolar? The molecule is nonpolar if the net molecular dipole moment is zero. The molecule is polar if the net molecular dipole moment is not zero. A. Polar molecule B. Nonpolar molecule

To answer Questions 5 through 8, you will probably find it helpful to draw a Lewis structure for the molecular formula C2Br2. The C atoms are bonded to each other and to one Br atom in this molecule. Space is provided below for you to draw your Lewis structure, but only the answers to the questions relating to this structure will be graded!

C2Br2
5. (2 points) What is the total number of valence electrons that should be shown explicitly as bonding pairs and/or lone pairs in the correct Lewis structure for C2Br2? A. 22 B. 23 C. 24 D. 25 E. 26

Part I continues on Page 3 2

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Part I All answers to questions on this page must be submitted on the bubble sheet, using a #2 pencil. Only answers submitted on the bubble sheet will be graded!!! PLEASE READ EACH QUESTION VERY CAREFULLY!!!
6. (4 points) Each carbon atom should be surrounded by the same number of electron groups if your Lewis structure is correct. What is the total number of electron groups surrounding each carbon atom in the correct Lewis structure for C2Br2? Use the definition of electron group that we discussed when we talked about VSEPR theory! A. 2 B. 3 C. 4

7. (4 points) What is the geometrical arrangement of electron groups surrounding each carbon atom in the correct Lewis structure for C2Br2? A. Trigonal planar B. Tetrahedral C. Linear

8. (4 points) Is this molecule polar or nonpolar? The molecule is nonpolar if the net molecular dipole moment is zero. The molecule is polar if the net molecular dipole moment is not zero. A. Polar molecule B. Nonpolar molecule

To answer Questions 9 through 12, you will probably find it helpful to draw a Lewis structure for the condensed structural formula (CH3)2CO. Remember, a condensed structural formula suggests the bonding connectivity. Space is provided below for you to draw your Lewis structure, but only the answers to the questions relating to this structure will be graded! Look at the carbon atom marked with the arrow below to answer Questions 10 through 12.

(CH3)2CO
9. (2 points) What is the total number of valence electrons that should be shown explicitly as bonding pairs and/or lone pairs in the correct Lewis structure for (CH3)2CO? A. 22 B. 23 C. 24 D. 25 E. 26

10. (4 points) Look at the carbon atom marked with the arrow above. What is the total number of electron groups surrounding this carbon atom in the correct Lewis structure for (CH3)2CO? Use the definition of electron group that we discussed when we talked about VSEPR theory! A. 2 B. 3 C. 4

11. (4 points) Look at the carbon atom marked with the arrow above. What is the geometrical arrangement of electron groups surrounding each carbon atom in the correct Lewis structure for (CH3)2CO? A. Trigonal planar B. Tetrahedral C. Linear

Part I continues on Page 4 3

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Part I All answers to questions on this page must be submitted on the bubble sheet, using a #2 pencil. Only answers submitted on the bubble sheet will be graded!!! PLEASE READ EACH QUESTION VERY CAREFULLY!!!
12. (4 points) Is the (CH3)2CO molecule polar or nonpolar? The molecule is nonpolar if the net molecular dipole moment is zero. The molecule is polar if the net molecular dipole moment is not zero. A. Polar molecule B. Nonpolar molecule

Questions 13 through 15 refer to the Lewis structure shown below. All valence electrons are shown explicitly in this structure, so you dont need to worry about adding lone pairs or bonds. Nonzero formal charges are not shown explicitly, however.

O H O C O 14

13. (4 points) What is the formal charge on the atom marked 13 in the structure on the left? A. 2 B. 1 C. 0 D. +1 E. +2

14. (4 points) What is the formal charge on the atom marked 14 in the structure on the left? A. 2 B. 1 C. 0 D. +1 E. +2

13

15. (4 points) What is the overall charge on the molecule shown at the left? A. 2 B. 1 C. 0 D. +1 E. +2

Questions 16 through 18 refer to the Lewis structure shown below. All valence electrons are shown explicitly in this structure, so you dont need to worry about adding lone pairs or bonds. Nonzero formal charges are not shown explicitly, however.

H H C H 16 C C H H 17

16. (4 points) What is the formal charge on the atom marked 16 in the structure on the left? A. 2 B. 1 C. 0 D. +1 E. +2

17. (4 points) What is the formal charge on the atom marked 17 in the structure on the left? A. 2 B. 1 C. 0 D. +1 E. +2

18. (4 points) What is the overall charge on the molecule shown at the left? A. 2 B. 1 C. 0 D. +1 E. +2

Part I continues on Page 5 4

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Part I All answers to questions on this page must be submitted on the bubble sheet, using a #2 pencil. Only answers submitted on the bubble sheet will be graded!!! PLEASE READ EACH QUESTION VERY CAREFULLY!!!
In Questions 19 through 24, you need to identify the functional groups that are circled in the lineangle structures below. The choices below should be used to answer all of these questions! Lone pairs are not shown explicitly in these lineangle structures, but every atom does have a formal charge of zero. A. B. alkene thiol C. D. aromatic ring alcohol E. F. ether carboxylic acid G. H. ester amine I. J. amide sulfide

20
NH2 H N O S N O Cefaclor
(an antibiotic)

19. (5 points) What functional group is circled and marked 19 in the structure of Cefaclor? Pick from the menu of choices given above. 20. (5 points) What functional group is circled and marked 20 in the structure of Cefaclor? Pick from the menu of choices given above.

19

Cl

21
HO O

21. (5 points) What functional group is circled and marked 21 in the structure of Cefaclor? Pick from the menu of choices given above.

22 23
O HN O H2N Oseltamivir
(an antiviral; used in treatment of influenza)

O O

22. (5 points) What functional group is circled and marked 22 in the structure of Oseltamivir? Pick from the menu of choices given above.

24

23. (5 points) What functional group is circled and marked 23 in the structure of Oseltamivir? Pick from the menu of choices given above. 24. (5 points) What functional group is circled and marked 24 in the structure of Oseltamivir? Pick from the menu of choices given above.

Part I continues on Page 6 5

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Part I All answers to questions on this page must be submitted on the bubble sheet, using a #2 pencil. Only answers submitted on the bubble sheet will be graded!!! PLEASE READ EACH QUESTION VERY CAREFULLY!!!
Questions 25 through 30 refer to the structure of Lunesta, which is shown below. This is a lineangle structure. Lone pairs are not shown explicitly, but every atom in this molecule has a formal charge of zero. Each of these questions refers to the structure of the entire molecule.

O N N N H O Lunesta
(a hypnotic; used in treatment of insomnia

25. (5 points) What is the total number of lone pairs present in the structure of Lunesta? There are 2 electrons in a lone pair.

Cl N

O N N CH3

A. B. C. D.

11 12 13 14

E. F. G. H.

15 16 17 18

I. J.

19 20

26. (5 points) What is the total number of hydrogen atoms present in the structure of Lunesta? A. B. C. D. 11 12 13 14 E. F. G. H. 15 16 17 18 I. J. 19 20

27. (5 points) What is the total number of pi electrons present in the structure of Lunesta. Each pi bond contains 2 pi electrons. This question is asking for the total number of pi electrons, not the total number of pi bonds! A. B. 11 12 C. D. 13 14 E. F. 15 16 G. H. 17 18 I. J. 19 20

28. (5 points) What is the total number of sp hybridized carbon atoms present in the structure of Lunesta. A. B. 0 1 C. D. 2 3 E. F. 4 5
2

G. H.

6 7

I. J.

8 9

29. (5 points) What is the total number of sp hybridized carbon atoms present in the structure of Lunesta. A. B. 5 6 C. D. 7 8 E. F. 9 10
3

G. H.

11 12

I. J.

13 14

30. (5 points) What is the total number of sp hybridized carbon atoms present in the structure of Lunesta. A. B. 5 6 C. D. 7 8 E. F. 9 10 G. H. 11 12 I. J. 13 14

Part I continues on Page 7 6

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Part I All answers to questions on this page must be submitted on the bubble sheet, using a #2 pencil. Only answers submitted on the bubble sheet will be graded!!! PLEASE READ EACH QUESTION VERY CAREFULLY!!!
Questions 31 through 34 refer to the structure of Zanamivir, which is shown below. This is a lineangle structure. Lone pairs are not shown explicitly, but every atom in this molecule has a formal charge of zero. Questions 31 and 32 refer to the structure of the entire molecule. Questions 33 and 34 refer to the specific bonds that are marked with the question number. 31. (5 points) How many of the alcohol functional groups present in Zanamivir can be classified as secondary (2 alcohols? )

HO

OH H HO HN OH O HN 34 HN 33 NH2 Zanamivir
(an antiviral; used in treatment of influenza)

A. B.

0 1

C D.

2 3

E. F.

4 5

32. (5 points) What is the total number of methyl groups present in the structure of Zanamivir? A. B. 0 1 C D. 2 3 E. F. 4 5

33. (5 points) What kinds of orbitals overlap to form the bond found in the single bond marked 33 in the structure of Zanamivir shown above? A. B. sp sp 2 2 sp sp
3 3

C. D.

spsp 3 2 sp sp

E. F.

sp sp 2 sp sp

G. H.

sp p 2 sp p

I. J.

spp pp

34. (5 points) What kinds of orbitals overlap to form the bond found in the double bond marked 34 in the structure of Zanamivir shown above? A. B. sp sp 2 2 sp sp
3 3

C. D.

spsp 3 2 sp sp

E. F.

sp sp 2 sp sp

G. H.

sp p 2 sp p

I. J.

spp pp

35. (5 points) An acyclic alkane has 8 carbon atoms. How many hydrogen atoms are present in this molecule? (A molecule is acyclic if its structure contains no rings.) A. B. 11 12 C. D. 13 14 E. F. 15 16 G. H. 17 18 I. J. 19 20

36. (5 points) Which functional group listed below does not contain any pi bonds within the characteristic grouping of atoms that defines its structure? A. alkyne B. aromatic ring C. alcohol D. ester E. acid anhydride

Part I continues on Page 8 7

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Part I All answers to questions on this page must be submitted on the bubble sheet, using a #2 pencil. Only answers submitted on the bubble sheet will be graded!!! PLEASE READ EACH QUESTION VERY CAREFULLY!!!
37. (5 points) Suppose that a nitrogen atom within a molecule is involved in one bond while also being surrounded by two lone pairs. What is the formal charge on this nitrogen atom? A. 2 B. 1 C. 0 D. +1 E. +2

38. (5 points) Which bond listed below has the largest bond dipole moment associated with it? A. OO B. OF C. ON D. OH E. OC

39. (5 points) Which statement below about resonance is false? A. Only electrons move in converting from one resonance structure to another. The positions of all atomic nuclei remain fixed. B. Every resonance structure must have exactly the same number of pi bonds and lone pairs. C. Octet structures are generally considered to have greater relative importance than non-octet structures. D. The overall charge of every resonance structure must be exactly the same. E. All of the statements listed in choices A through D are false. F. None of these statements listed in choices A through D is false. In Questions 40 through 42, the lineangle structure of an alkane is given. Pick the choice which best describes the correct name of this alkane. 40. (4 points) What is the correct name of the alkane shown at the left? A. B. C. D. E. 2,2,3,4-Tetramethylpentane 2,3,4,4-Tetramethylpentane 2-tert-Butyl-3-methylbutane 2,2-Dimethyl-3-isobutylbutane None of the above

Question 40

41. (4 points) What is the correct name of the alkane shown at the left? A. B. C. D. E. 2,6-Diethyl-5-methyloctane 3,7-Diethyl-4-methyloctane 3-Ethyl-4,7-dimethylnonane 7-Ethyl-3,6-dimethylnonane None of the above

Question 41

42. (4 points) What is the correct name of the alkane shown at the left? A. B. C. D. E. 5,8-Dimethyl-4-propylnonane 2,5-Dimethyl-4-propylnonane 4-Isobutyl-5-methylnonane 4-sec-Butyl-5-methylnonane None of the above

Question 42

End Part I. Part II begins on Page 9 8

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Part II Write your answers to all questions on this page in the space provided. If you use a pen, only blue or black ink is acceptable!!! PLEASE READ EACH QUESTION VERY CAREFULLY!!!
In Questions 4345, draw the indicated number of resonance structures in the large boxes provided. Be sure to show all lone pairs and nonzero formal charges! (Note: If you think there are more than the indicated number of resonance structures, it is probably because you are writing structures that are relatively unimportant. The structures you draw in the boxes should be those of relatively greatest importance.) After you draw your structures, indicate which structure is the most important contributor to the true structure of the resonance hybrid by placing the symbol X in the small box beneath it. If you think all of the structures are equally important, mark the box labeled All structures are equivalent with the symbol X. If your answers are correct, you will either find that all structures are equivalent, or there will be one that is clearly more important than the others!!! 43. (20 points) Draw 3 resonance structures for the following polyatomic anion:

CO32

All structures are equivalent


44. (15 points) Draw 2 additional resonance structures.

H C H C H

H C N H H

All structures are equivalent

Page Total

Part II continues on Page 10 9

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Part II Write your answers to all questions on this page in the space provided. If you use a pen, only blue or black ink is acceptable!!! PLEASE READ EACH QUESTION VERY CAREFULLY!!!
45. (15 points) Draw 2 additional resonance structures.

H3C

All structures are equivalent

In Questions 46 and 47, draw a lineangle structure for the alkane name given. Write your answer in the box below the name. You must draw lineangle structures to receive full credit for these questions! 46. (8 points) 3,5-Dimethyl-4-isopropylheptane 47. (8 points) 4-tert-Butyl-2,5-dimethyloctane

48. (11 points) The alkane name given below is incorrect. Use this incorrect name to draw a line-angle structure for the molecule. Draw this lineangle structure in the box below the incorrect name. Then, give the correct name of the compound in the box below the label CORRECT NAME. INCORRECT NAME = 7-Isobutyl-3-isopropyldecane

CORRECT NAME

Page Total

Part II continues on Page 11 10

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Part II Write your answers to all questions on this page in the space provided. If you use a pen, only blue or black ink is acceptable!!! PLEASE READ EACH QUESTION VERY CAREFULLY!!!
49. (40 points) There are eight (8) constitutional isomers having molecular formula C6H14O that can also be classified as primary (1 alcohols. Draw a structure for each of these primary alcohols, one ) structure per box below. You may use any valid convention we have discussed (e.g. complete Lewis structure, condensed structural formula, line-angle formula) to draw your structures. This question will be graded as follows: +5 for each correct, unique, primary alcohol structure +0 for each incorrect structure, or for a structure that is not a primary alcohol 1 for each repeated structure (i.e. if you draw the same structure more than once, 1 point will be deducted for each repetition)

Page Total

END OF EXAM!!! 11

The Modern Periodic Table of the Elements


18

Hydrogen

Element name

Mercury

Helium

1.01

Average relative masses are 2001 values, rounded to two decimal places.

2.1

80
Symbol
13
Boron Carbon Nitrogen Oxygen

Atomic #
14 6 12.01
2.5
Silicon

He
15 7 14.01
3.0
Phosphorus

16 8 16.00
3.5
Sulfur

17
Fluorine

4.00
--Neon

Lithium

Beryllium

Hg
Avg. Mass
10.81
2.0
Aluminum

10

6.94

Li Electronegativity
13 14 15

9.01

Be

200.59
B C N

19.00
4.0
Chlorine

20.18
--Argon

Ne

1.0

1.5

All average masses are to be treated as measured quantities, and subject to significant figure rules. Do not round them further when performing calculations.

1.9
Al
26.98

Sodium

Magnesium

11

12

16

17

18

Na
4
Titanium Vanadium Chromium Manganese Iron Cobalt Nickel Copper Zinc Gallium

Mg
5 23 24 25 26 27 28 29 30 31 6 7 8 9 10 11 12
1.5

Si
28.09
1.8
Germanium

P
30.97
2.1
Arsenic

S
32.07
2.5
Selenium

Cl
35.45
3.0
Bromine

Ar
39.95
--Krypton

22.99

0.9

24.31

1.2

3 22

Potassium

Calcium

Scandium

19

K Ti
47.88
1.5
Niobium Molybdenum Technetium Ruthenium Rhodium Palladium Silver Cadmium

20

21

32

33

34

35

36

39.10 50.94
1.6 1.6 1.5 1.8 1.8 1.8 1.9 1.6

Ca
52.00 54.94 55.85 58.93 58.69 63.55 65.39
Zirconium

Sc

Cr

Mn

Fe

Co

Ni

Cu

Zn

Ga
69.72
1.6
Indium

Ge
72.61
Tin

As
1.8

Se
74.92
2.0
Antimony

Br
78.96
2.4
Tellurium

Kr
79.90
2.8
Iodine

0.8

40.08

1.0

44.96

1.3

83.80

3.0
Xenon

Rubidium

Strontium

Yttrium

37

38

39

40

41

42

43

44

45

46

47

48

49

50

51

52

53

54

Rb
91.22
1.4
Tantalum Tungsten Rhenium Osmium Iridium Platinum

Sr
92.91
1.6 1.8 1.9 2.2 2.2 2.2
Gold

Y
95.94 (98) 101.07 102.91 106.42 107.87
1.9
Hafnium

Zr

Nb

Mo

Tc

Ru

Rh

Pd

Ag

Cd
112.41
1.7
Mercury

In
114.82
1.7
Thallium

Sn
118.71
1.8
Lead

Sb
121.76
1.9
Bismuth

Te
127.60
2.1
Polonium

I
126.90
2.5
Astatine

Xe
131.29
2.6
Radon

85.47

0.8

87.62

1.0

88.91

1.2

Cesium

Barium

Lutetium

55

56

Cs
178.49
1.3
Dubnium Seaborgium Bohrium Hassium Meitnerium

Ba
180.95
1.5 1.7 1.9 2.2 2.2

57-70

71

72

73

74

75

76

77

78

79

80

81

82

83

84

85

86

132.91
Rutherfordium

0.7

137.33

*
183.84 186.21 190.23 192.22 104 (261)
-----------

Lu

Hf

Ta

Re

Os

Ir

Pt
195.08
2.2
Ununnilum

Au
196.97
2.4
Unununium

Hg
200.59
1.9
Ununbium

Tl
204.38
1.8

Pb
207.20
1.8
Ununquadium

Bi
208.98
1.9

Po
(209)
2.0

At
(210)
2.2

Rn
(222)
2.4

0.9

174.97

1.1

Francium

Radium

Lawrencium

87

88

(223)

Fr
(262) (263) (262) (265)

(226)

Ra

89-102

103

105

106

107

108

109 (266)
---

110

111

112

114

**

(262)

Lr

Rf

Db

Sg

Bh

Hs

Mt

Uun
(271)
---

Uuu
(272)
---

Uub
(277)
---

Uuq
(289)
---

0.7

0.9

---

Lanthanum

Cerium

Praseodymium

Neodymium

Promethium

Samarium

Europium

Gadolinium

Terbium

Dysprosium

Holmium

Erbium

Thulium

Ytterbium

*lanthanides Ce
140.12
1.1
Protactinium Uranium

57

58

59

60

61

62

63

64

65

66

67

68

69

70

La
140.91
1.1 1.1

Pr
144.24

Nd

Pm
(145)
1.1
Neptunium

Sm
150.36
1.2
Plutonium

Eu
151.97
1.1
Americium

Gd
157.25
1.2
Curium

Tb
158.93
1.1
Berkelium

Dy
162.50
1.2
Californium

Ho
164.93
1.2
Einsteinium

Er
167.26
1.2
Fermium

Tm
168.93
1.3
Mendelevium

Yb
173.04
1.1
Nobelium

138.91
Thorium

1.1

Actinium

**actinides Th
232.04
1.3 1.5

89

90

91

92

93

94

95

96

97

98

99

100

101

102

Ac
231.04

Pa

U
238.03
1.4

Np
(237)
1.4

Pu
(244)
1.3

Am
(243)
1.3

Cm
(247)
1.3

Bk
(247)
1.3

Cf
(251)
1.3

Es
(252)
1.3

Fm
(257)
1.3

Md
(258)
1.3

No
(259)
1.3

(227)

1.1

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