1. What is the molecular formula of limonene, the major volatile compound in orange peel oil?
a.
C10H18
b.
C10H20
c.
C10H16
d.
C11H14
e.
C11H18
ANSWER:
c
2. Of those indicated, which would be the shortest carbon-carbon bond in -selinene?
A
B
C
D
E
b
3. What would be the ideal value for the indicated bond angle?
120°
90°
104°
180°
109°
e
4. Which structure matches the following condensed structure?
a
5. Which one of the following structures must be incorrect?
6. Which of the following is not a resonance structure of the others?
7. Which one of the resonance structures below would be the most important (i.e., most stable)?
d
8. How many atoms in ethene are required by sp2 bonding to lie in the same plane?
2
3
4
5
6
9. Which one of the following structures is not chemically identical to the others?
10. Which of the following pairs are not resonance structures of each other?
All are pairs of resonance structures.
11. How many hydrogen atoms are part of the following steroid?
18
20
21
22
24
12. In the following molecule, how many carbon atoms are in the sp3 hybridization state?
11
13. In the following molecule, how many carbon atoms are in the sp2 hybridization state?
0
1
14. In the following molecule, how many carbon atoms are in the sp hybridization state?
12
None of the above.
15. The lone-pair of electrons on nitrogen in the following molecule reside in what type of orbital?
sp3
sp2
sp
2p
2s
16. In the following molecule, how many carbon atoms are in the sp2 hybridization state?
7
8
9
17. The boxed item most likely represents what?
s orbital
sp3 orbital
p orbital
could be any of A–C
18. The following molecule contains how many carbon atoms in the sp hybridization state?
13
16
19. The nitrogen of trimethylamine [(CH3)3N] contains how many lone pairs of electrons?
none
one
two
three
there is no nitrogen in this molecule
20. A positive charge on oxygen generally occurs when:
oxygen has too many electrons.
oxygen has too few electrons.
oxygen is sharing one of its non-bonding electron pairs.
oxygen has too many non-bonding electron pairs.
oxygen is borrowing electrons from another atom.
21. The carbon atom in CH2Cl2 has what hybridization?
sp4
they are not hybridized
22. The molecular formula for piperitone is
C9H16O
C10H18O
C9H18O
C10H14O
C10H16O
23. Which structure is different from the others?
CH3CHClCH(CH3)2
All are identical.
24. A fairly common algal metabolite is the compound (-)-geosmin, which imparts a musty odor to water even at concentrations in the ppb range. What is the molecular formula of geosmin?
C11H20O
C12H22O
C11H21O
C12H20O
C12H21O
25. Which of the carbon-carbon bonds indicated would you expect to be the longest in stilbene?
26. Which of the following pairs are not resonance structures of each other?
27. The following molecule has what molecular formula?
C39H58O
C40H58O
C39H60O
C44H44O
28. What is the molecular formula of carvone, the major volatile compound in caraway oil?
C10H17O
C10H15O
29. Of those indicated, which would be the shortest carbon-carbon bond in -cadinene?
30. What would be the ideal value for the indicated bond angle?
31. Which structure matches the following condensed structure?
32. Which one of the following structures must be incorrect?
33. How many sp2 hybridized carbon atoms are in the potent anticancer compound hydroxymethylacylfulvene?
34. In the following molecule, how many carbon atoms are in the sp3 hybridization state?
35. Which of the following statements are true of sp orbitals?
Orbitals of the sp type are 50% s and 50% p character.
They are hybrid orbitals.
They are linear.
They result when one s orbital and one p orbital are mixed.
All are correct.
36. Which of the following molecules are most likely to be held together by a purely covalent bond?
NaCl
H2
HF
BH3
KI
37. What is the molecular formula of camphor?
C11H18O
C11H16O
38. Camptothecin is an important anticancer compound; how many carbons are in the sp hybridization state?
39. How many sp3 carbons are in the following molecule?
40. The process of adding electrons one by one to atomic orbitals beginning with the lowest energy is described by:
the Aufbau Principle.
Hund's Rule.
the de Broglie Relation.
the Pauli Exclusion Principle.
Coulomb's Law.
41. Which of the following cannot be a correct Lewis structure?
42. How many different resonance structures can be drawn for the benzyl cation (shown below) which place the plus charge on a carbon atom in the ring?
43. Which of the following represent resonance contributing Lewis structures for CH2N2?
both A and B are correct
44. The following molecule belongs to a class of compounds known as allenes. Based on your knowledge of bonding, predict the hybridization of the carbon atom indicated by the arrow.
p-p pi
a hypervalent carbon
45. How many isomers of C4H9Br are possible?
four
five
six
46. How many isomers of C5H12 are possible?
47. Which of the following most correctly defines "structural isomers"?
molecules with different molecular formulas but the same connectivity
compounds that are not constitutional isomers
molecules with the same molecular formula but different connectivity
Anti and gauche conformers
both B and C
48. How many structural isomers exist for the formula C6H14?
49. A hydrocarbon with a double bond and a ring will have the general formula?
CnH2n+2
CnH2n
CnH2n-2
CnH2n-4
C2nH2n
50. What is the hybridization of the each of the labeled atoms for the potent neurotoxin (-)-gephyrotoxin?
A = sp2, B = sp, C = sp2, D = sp3, E = sp3
A = sp2, B = sp, C = sp3, D = sp3, E = sp2
A = sp2, B = sp, C = sp2, D = sp3, E = sp2
A = sp2, B = sp, C = sp3, D = sp3, E = sp3
A = sp, B = sp, C = sp3, D = sp3, E = sp3
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