Mary Mae D.

Vitor 58/65
BS CHEM- 4H2
1. How many electrons occupy the bonding molecular orbitals 16. Which of the following compounds may be classed as a
of a CN triple bond? protic solvent?
A) 2 B) 4 C) 6 D) 8 A) Tert-butanol B) diethyl ether
2. Which of the following species is not amphoteric ? C) n-hexane D) acetone
A) NH3 B) HF C) NH4(+) D) HCO3(-) 17. Which of the following compounds has a C-H bond with
3. What is the relationship of the two structures shown the lowest bond dissociation energy?
below? A) C2H6 B) C6H6
C) C2H2 D) CH3CH=CH2
18. The H–C–O bond angle in H2C=O (formaldehyde) is
approximately .....
A) 90º B) 109º.
A) they are identical
C) 120º D) 180º.
B) they are conformations of the same structure
19. Which of the following species has a planar molecular
C) they are constitutional isomers
configuration?
D) they are different compounds with different
A) SO3-2
compositions
B) SO3
4. Which of the following molecules will not have a dipole
C) SOCl2
moment?
D) SO2Cl2
A) CH3Cl B) CH3OCH3
20. Which of the following compounds does not have a planar
C) CH2Cl2 D) CCl4
molecular configuration?
5. Which of the following molecules has a dipole moment?
A) H2C=CH2
A) CBr4 B) CH2=CH2
B) H2C=CH–C≡CH
C) BF3 D) SO2
C) H2C=C=CH2
6. Which of the following molecules has a linear shape?
D) H2C=C=C=CH2
A) NH3 B) H2S
21. Which of the following compounds has no isomer?
C) CO2 D) H2CO
A) CH3CH2CH2Cl
7. Which of the following intermediates is pyramidal in
B) CH3CHO
shape?
C) CH2=CHCl
A) H3C(+) B) H2C:
D) ClCH2CH2Cl
C) H3C:(-) D) HC≡C:(-)
22. Which of the following statements about carbon is not
8. In which compound does carbon have the highest oxidation
correct?
state?
A) carbon forms strong covalent bonds to itself,
A) CH4 B) HCN
allowing chains and rings to be made.
C) H2CO D) CH2Cl2
B) carbon expands its valence shell to accomodate
9. Which of the following statements applies to a C10H14O2
more than eight electrons and thus forms double
compound?
and triple bonds.
A) it may have 2 double bonds and 2 rings
C) carbon forms strong covalent bonds to elements like
B) it may have 3 double bonds and 0 rings
nitrogen and oxygen because it does not have lone
C) it may have 1 triple bond and 3 rings
pairs of valence electrons to destabilize the bonds.
D) it may have 0 double bonds and 3 rings
D) carbon and hydrogen have similar electronegativity
10. What functional group is present in the terpene camphor?
and form strong bonds to each other, thus avoiding
the high reactivity shown by metal hydrides.
23. What is the IUPAC name for CH3CH2C(CH3)2CH2CH(CH3)2?
A) 3,3,5-trimethylhexane
B) 2,2,5-trimethylhexane
C) 2,4,4-trimethylhexane
A) Hydroxy B) carboxy
D) 1,1,3,3-tetramethylpentane
C) carbonyl D) oxy
24. Limiting your answer to cycloalkanes and ignoring
11. What functional class is represented by the alkaloid
stereoisomers, how many C6H12 constitutional isomers are
coniine?
there?
A) 6
B) 9
C) 11
D) 13
A) amine B) imine
25. The IUPAC name for (CH3)2CHCH(CH3)CH2CH=CH2 is ...
C) amide D) nitrile
A) 4,5-dimethyl-1-hexene
12. Which of the following compounds would be considered
B) 4,5,5-trimethyl-1-pentene
an electrophilic reagent?
C) 2,3-dimethyl-5-hexene
A) NH3 B) Br2
D) 4-methyl-4-isopropyl-1-butene
C) CH3OH D) NH2OH
26. A C6H12 compound reacts with ozone to yield a single
13. Which of the following compounds would you expect to
C3H6O product. Gas phase free radical bromination of the
be most soluble in water?
hydrocarbon gives a single C6H11Br product. A likely
A) CH2Cl2 B) C6H12 (cyclohexane)
identification of this compound is ..
C) CH3CH2OH D) C2H5OC2H5
A) cyclohexane
14. The following compounds have similar molecular weights.
B) cyclohexene
Which has the highest boiling point?
C) 3-hexene
A) CH3CH=O B) C2H5OH
D) 2,3-dimethyl-2-butene
C) CH3OCH3 D) CH3CH2CH3
27. What makes carbon such a unique element?
15. Which of the following compound pairs are constitutional
(a) Elemental carbon comes in two forms, diamond and
isomers?
graphite.
A) CH3CH2OCH3 and CH3CH2CHO
(b) Carbon forms four bonds, although the ground state
B) CH3CH2CHO and CH3CH2CH2OH
configuration would predict the formation of fewer bonds.
C) CH3COCH2CH3 and CH3CH2COCH3
(c) Carbon forms covalent bonds rather than ionic bonds.
D) CH3CH2CH2CHO and CH3COCH2CH3
(d) To a greater extent than any other element, carbon can
bond to itself to form straight chains, branched chains and
rings.
28. The hybridization of carbon atoms in alkanes is
(a) sp
(b) sp2
(c) sp3
(d) sp3d
29. A molecule with the formula C3H8 is a(n):
(a) hexane
(b) propane
(c) decane (a) 6-ethyl-4-methylcyclohexene
(d) butane (b) 6-ethyl-3-methylcyclohexene
(e) ethane (c) 3-ethyl-5-methylcyclohexene
30. Select the correct IUPAC name for: (d) 6-ethyl-4-methylcyclohex-1-ene
37. What is the IUPAC name of the following compound?

(a) 2,6-diethyl-3-nonyne
(a) 5-methyl-5-ethyloctane (b) 2,5-diethyl-3-nonyne
(b) 5-methyl-5-propylheptane (c) 3,7-dimethyl-5-nonyne
(c) 4-ethyl-4-methyloctane (d) 3,7-dimethyl-4-nonyne
(d) 3-methyl-3-propyloctane 38. Which of the following formulas represents an alkene?
31. Select the correct IUPAC name for: (a) CH3CH2CH3
(b) CH3CH3
(c) CH3CH2CHCH2
(d) CH3CH2Cl
39. What is the name of the following compound?

(a) 1,1,3-trimethylpentane
(b) 1-ethyl-1,3-dimethylbutane
(c) 2,4-dimethylhexane
(d) 3,5-dimethylhexane
32. Select the correct IUPAC name for:

(a) 1,3-dibromophenol
(b) 2,5-dibromophenol
(c) 2,6-dibromophenol
(a) 1,4-dimethylcyclopentane
(d) m-dibromophenol
(b) 1,3-dimethylcyclopentane
40. Which one of the following is a secondary alcohol?
(c) 2,5-dimethylcyclopentane
(a) CH3CH2OH
(d) 2,3-dimethylcyclopentane
(b) CH3OH
33. The general formula for noncyclic alkenes is:
(c) CH3CH(OH)CH3
(a) CnH2n+2
(d) (CH3)C3OH
(b) CnH2n
41. Select the IUPAC name for: (CH3)2CHCH(OH)CH2C(CH3)3.
(c) CnH2n-2
(a) 2,5,5-trimethyl-3-hexanol
(d) CnHn+2
(b) 1,1,4,4-pentamethylbutanol
(e) CnHn
(c) 1,1-dimethylisopentanol
34. The correct name for the compound given below is:
(d) 2,5-dimethyl-4-hexanol
42. Which is NOT a physical property of alcohols or phenols?
(a) Phenols are generally only slightly soluble in water.
(b) The solubilities of normal primary alcohols in water
decrease with increasing molecular weight.
(c) The hydroxyl group of an alcohol is nonpolar.
(d) Due to hydrogen bonding, boiling points of alcohols are
(a) 2-methyl-1-butene much higher than those of corresponding alkanes.
(b) 2-ethyl-1-propene 43. Give the IUPAC name of this compound: CH3OCH2CH3.
(c) 2-ethyl-1-pentane (a) dimethyl ether
(d) 3-methyl-2-butene (b) methoxyethane
35. Select the best name for: (c) methylethyloxide
(d) propyl ether
44. Given that the energy of a CH3-H bond is 104 kcal/mol and
that of an HO-H bond is 119 kcal/mol, what is the bond
dissociation energy of the following reaction?

a. 15 kcal/mol
(a) 4-ethyl-cis-3-octene b. -15 kcal/mol
(b) 4-ethyl-trans-3-octene c. 223 kcal/mol
(c) 4-butyl-cis-3-hexene d. -223 kcal/mol
(d) 5-ethyl-trans-5-octene 45. Given that the energy of a CH3bond is 104 kcal/mol,
36. Name the following compound: CH3-Cl bond is 85 kcal/mol, H-Cl bond is 103 kcal/mol and that
of an Cl2 bond is 58 kcal/mol, what is the bond dissociation
energy of the following reaction?
 d. Alkynes are generally more reactive than alkenes
57. Alcohols react using both acid and base catalysis: please
a. 25 kcal/mol elaborate.
b. -25 kcal/mol a. Acids catalyze hydrolysis and ether formation from
c. 189 kcal/mol alcohols. Bases polarize the OH bond, even to the
d. -166 kcal/mol point of forming an alkoxide salt.
46. What are common methods for preparing benzyne? b. Acids are used as catalysts in the Williamson ether
a. Elimination from organolithium or synthesis and for hydrolysis of ethers. Bases dissolve
organomagnesium precursors in ethers for use in other reactions.
b. loss of neutral leaving group c. Acids and bases will react in alcohols to form salts
c. photolytic and/or pyrolitic methods that are useful for ether synthesis.
d. All of the above d. Acids catalyze alcohol dimerization to ethers while
47. What is the major product of the radical reaction of bases hydrolyse them.
2-methylbutane with Cl2? 58. The Williamson ether synthesis involves which of the
a. 2-chloro-2-methylbutane following?
b. 1-chloro-2-methylbutane a. The two Williamson reagents normally used in
c. 3-chloro-2-methylbutane combination with heat and light.
d. 4-chloro-2-methylbutane b. An alkyl alcohol heated up with acid to distill off
48. What is the relationship between the two compounds water.
below? c. An alkoxide salt of an alcohol reacted with a primary
or secondary halide.
d. An alkoxide salt of an alcohol reacted with the
alcohol it was made from.
59. Epoxides are a special kind of ether that:
a. are reactive because of the ring string (3 membered
ring).
a. Same compound b. react faster with acid or base catalysis.
b. Structural isomers c. can react with amines, alcohols and acids.
c. Enantiomers d. all of the above.
d. Diastereomers 60. Ethers can react with which of the following?
49. Which of the following statements about chirality is a. With base and water to give two alcohols.
incorrect? b. With acid and another alcohol to give
a. A chiral center is an atom that is tetrahedrally transesterification - another ether and a different
bonded to four different groups. alcohol from the starting one.
b. A chiral molecule has a superimposable mirror c. With ethyl bromide to give an ethyl ether and a new
image. alkyl bromide.
c. A chiral molecule does not have any reflective d. With a carboxylic acid and heat to give an ester and
symmetry. an alcohol.
d. All chiral molecules may exist as enantiomers. 61. Alcohols are unique in forming ethers because:
50. Which of the following alkyl halides would be suitable to a. they can react with themselves in the presence of
use when forming a Grignard reagent? heat and acid to give ethers.
a. CH3CH2CH(OH)CH2Br b. they have an exchangeable hydrogen (the OH one).
b. BrCH2CO2H c. they have higher boiling points than hydrocarbons or
c. PhCH2CH2Br ethers with the same number of carbon atoms.
d. None of these are suitable d. they are all of the above.
51. A spontaneous interconversion between two isomers 62. Ether alcohols (molecules with both an ether and a beta
usually with the change in position of a H atom. alcohol) can best be made by:
a. Tautomerism b. Polarization a. acid catalyzed reaction of an epoxide and an alcohol
c. Stereoisomerism d. Hydrogenation with maybe a little heat.
52. A reduction of carboxylic acid using hydride reagents b. addition of an alcohol to an alkene with base
gives what product? catalysis and heat.
a. Alcohol b. Carboxylic acid c. acid catalyzed addition of water to a vinyl ether
c. Ketone d. Ester (ether with a double bond next to the oxygen).
53. Which of the following objects is CHIRAL? d. addition of an alcohol to a ketone in the presence of
a. Basketball b. Glove acid and heat.
c. Fork d. Screw 63. There are many ways to make an ether including:
54. Markovnikov’s rule states that, in the addition of HX to an a. reaction of two alcohols with base and heat catalysis.
alkene, _____ is formed as the intermediate. b. reaction of an epoxide with an alkene using acid
a. The more substituted carbocation catalysis.
b. The least substituted carbocation c. reaction of an alkoxide and an alkyl bromide.
c. No carbocation d. addition of water to an epoxide with base catalysis.
d. The methyl carbocation 64. An epoxide reacts with an alkoxide to give an ether plus
55. Molecules that are not identical to their mirror images are something else:
kinds of stereoisomers are called a. and the something else is another alkoxide.
a. Diastereoisomers b. and the something else is NaOH.
b. Enantiomers c. and the something else is another epoxide.
c. Racemic d. and there is nothing else formed.
d. Meso compounds 65. Ethers are pretty good solvents for:
56. Which of the following statements correctly describes the a. alkyl halides.
general reactivity of alkynes? b. lithium alkyl and sodium alkoxide salts.
a. An alkyne is an electron-rich molecule and therefore c. alcohols.
reacts as a nucleophile d. all of the above to some extent.
b. The sigma bonds of alkynes are higher in energy than
the pi bonds and are thus more reactive
c. Unlike alkenes, alkynes fail to undergo electrophilic
addition reactions