1 Which of the following accurately represents the hybridizations for the carbon atoms in C2H6 (ethane), C2H4 (ethene),

), and
C2H2 (ethyne)?

Choose one A. sp, sp3 and sp2, respectively

answer.
B. sp3, sp2, and sp, respectively

C. sp2, sp, and sp3, respectively

D. sp, sp, and sp2, respectively

2 Which of the following accurately represents the molecular geometry for the carbon atoms in
C2H6 (ethane), C2H4 (ethene), and C2H2 (ethyne)?

Choose one A. Linear, tetrahedral, and planar, respectively

answer.
B. Tetrahedral, Linear, and planar, respectively

C. Linear, Linear, and planar, respectively

D. Tetrahedral, planar, and linear, respectively

3 What are the formal charges on the nitrogen and boron atoms in H3N - BH3, respectively?

Choose one A. +1, -1

answer.
B. +1, +1

C. -1, -1

D. -1, +1

4 What is the term used to describe the electrostatic attraction of the electrons of one molecule or atom for the nuclei of
another?

Choose one A. Van der Waals attraction

answer.
B. Hydrogen bonding

C. Ionic bonding

D. Covalent bonding

5
Fill in the blank. The strongest type of intermolecular force occurring between neutral molecules is the
__________________.

Choose one A. Covalent bond

answer.
B. Ionic bond

C. Van der Waals force

D. Hydrogen bond
6
When the products of a chemical reaction are more stable energetically than the reactants, energy is released as heat. This
type of reaction is referred to as which of the following?

Choose one A. Exothermic

answer.
B. Endothermic

C. Analgesic

D. Endodermic

7
Fill in the blank. A high energy transition state must be reached for chemical bonds to be broken and products formed in a
chemical reaction. The amount of energy needed to reach this transition state is known as the _________________.

Choose one A. Trans energy

answer.
B. Static energic

C. Kinetic energy

D. Activation energy

8
Fill in the blank. In an acid-base reaction, proton donors are __________________.

Choose one A. Bronsted acids

answer.
B. Lowry Bases

C. Bronsted-Lowry Acids

D. Bronsted-Lowry Bases

9 In general, what is the strongest effect on the acidity of a molecule, even more important than bond
strength?

Choose one A. Anion effect

answer.
B. Cation effect

C. Hydrogen effect

D. Hydroxide effect

10
In a chemical reaction, what is the species that supplies a pair of electrons to form a covalent bond
called?

Choose one A. Lewis acid

answer.
B. Hydrogen species

C. Lewis protons

D. Lewis base
11
The molecular formula CnH2n-2 is the general formula for which group of hydrocarbons?

Choose one A. Alkanes

answer.
B. Alkenes

C. Cycloalkanes

D. Alkynes

See Section 2.1

12
The prefixes eth-, but-, hex-, and hept, represent hydrocarbon chains having how many carbon atoms?

Choose one A. 2, 4, 6, 7, respectively

answer.
B. 2, 6, 4, 7, respectively

C. 4, 2, 7, 6, respectively

D. 2, 7, 6, 4, respectively

See Section 2.1

13
In which reaction type does the number of σ-bonds in the substrate decrease as new π-bonds are formed?

Choose one A. Elimination

answer.
B. Substitution

C. Addition

D. Combustion

See Section 2.3

14
In the which of the following reaction types does the number of σ-bonds in the substrate molecule increase? In addition, in
this reaction type, one or more π-bonds are usually lost.

Choose one A. Elimination

answer.
B. Addition

C. Substitution

D. Combusion

See Section 2.3

15
Which type of reaction is characterized by replacement of an atom or group by another; in this reaction type, the number of
bonds does not change except for the added groups?

.
Choose one A. Elimination
answer.
B. Addition

C. Substitution

D. Free radical

See Section 2.3

16 What is the product of a rearrangement reaction called?

Choose one A. A free radical

answer.
B. A carbocation

C. An isotope

D. An isomer

See Section 2.3

17
Carbon radicals are characterized by a lone electron on the carbon atom and have a total of how many valence electrons?

Choose one A. Seven

answer.
B. Four

C. Eight

D. One

See Section 2.3

18
Electrophiles are attracted to which of the following molecules?

Choose one A. Both NH3 and NH4+

answer.
B. Both CH3 O- and NH3

C. Both CH3O- and K +

D. NH3, NH4+, CH3O-, and K +

See Section 2.4

19
Nucleophiles are electron rich species or groups. Which of the following is an example of a nucleophile?

Choose one A. NH4+

answer.
B. H3O+

C. NH3

D. CH3OH

See Section 2.4.

20 A base is defined by its ability to accept which of the following?

Choose one A. An electron

answer.
B. A free radical

C. A neutron

D. A proton

See Section 2.4

21
Which of the followingis the correct line formula for3-methylpentane?

Answer:

See Section 3.1

Correct answer: CCC(C)CC

22
Which of the followingis the correct line formula for tert-butylcyclopentane?

Answer:

See Section 3.1

Correct answer: CC(C)(C)C1CCCC1

23
WWhich of the followingis the correct formula for 3-ethyl-5-methyloctane?

Answer:

See Section 3.1

Correct answer: CCCC(C)CC(CC)CC

24 Which of the followingis the correct formula for sec-butylcyclobutane?

Answer:

See Section 3.1

Correct answer: CCC(C)C1CCC1

25
The stereoisomer trans-1,3-dimethylcyclopentane is represented by which of the following structures?

Answer:

See Sections 3.3 and 3.4

Correct answer: C[C@@H]1CC[C@@H](C)C1

26
In which of the following cyclohexane structures is a Cl group cis to a methyl group?

Answer:

See Sections 3.3 and 3.4

Correct answer: C[C@@H]1CCCC[C@@H]1Cl

27 Which of the following statements is true concerning conformations of ethane?

Choose one A. The staggered conformation is the most stable.

answer.
B. The eclipsed form is the most stable.

C. The staggered and the eclipsed form have the same energy.

D. There are three stable staggered forms and two unstable eclipsed forms.

See section 3.2

28 What is the reactivity order of halogens from most reactive to least reactive?

Choose one A. Cl, F, Br, I

answer.
B. Cl, Br, I, F

C. F, Cl, Br, I

D. I, Br, Cl, F

See Section 3.5

29 Which of the following is the most stable conformationof ethane?

Choose one A. Anti

answer.
B. Gauche

C. Eclipsed

D. Fully eclipsed

See Section 3.2

30 The product of the reaction of CH4 + O2 + heat yields which of the following?

Choose one A. 2 CO2+ 2H2O + heat

answer.
B. CO2+ 2H2O + heat

C. 2 CO2+ 3H2O + heat

D. CO2+ 3H2O + heat

See Section 3.5

31 What is the major product from the reaction of butane with chlorine gas in the presence of heat or light?

Answer:

See Sections 3.5

Correct answer: CCC(C)Cl

32
2-isopropylpentane reacts with Br2 + energy to produce several monohalogenated isomeric
products. What is the least stable product produced?

Answer:

See Sections 3.5

Correct answer: CC(C)C(C)CCBr

33 Carbocation intermediates can react further to do which of the following?

Choose one A. Give a substitution product when the cation bonds to a nucleophile
answer.
B. Give an alkene product when the cation transfers a beta-proton to a base

C. Produce a substitution or an elimination after carbocation rearrangement

D. All of the above

See Section 4.2.4

34 Complete the sentence: Elimination from 2-iodobutane produces all of the following EXCEPT:

Answer:

See Section 4.2.4

Correct answer: CC=CC

35 Complete the sentence. The SN2 mechanism is favored by all of the following, EXCEPT:

Choose one A. Primary alkyl halides

answer.
B. Nonpolar aprotic solvent

C. Tertiary alkyl halides

D. Less substituted alkyl halides

See Section 4.2.3

36 Which of the following nucleophilic mechanisms is bimolecular and occurs via a single step with an inversion of configuration
at the alpha carbon?

Choose one A. SN3

answer.
B. SN1

C. SN2

D. E2

See 4.2.3

37 What is the correct molecular structure for isobutylbromide?

Answer:

See Section 4.1.1

Correct answer: CC(C)(C)Br
38 What is the molecular structure of 1,2-dibromocyclohexane?

Answer:

See Section 4.1.1.

Correct answer: BrC1CCCCC1Br

39 The SN1 reaction mechanism is unimolecular, goes through a carbocation intermediate, and follows a rate law equation that is
of what order?

Choose one A. First order

answer.
B. Zero order

C. Third order

D. One half order

See Section 4.2.3

40 Fill in the blank. Compounds that have the same sequence of covalent bonds but differ in the relative position of the atoms in
space are __________________.

Choose one A. Constitutional isomers

answer.
B. Stereoisomers

C. Tautomers

D. Stable structural isomers

See Section 4.1.3.

41 Which of the following are stereoisomers that are non-superimposable mirror images?

Choose one A. Diastereomers

answer.
B. Meso compounds

C. Enantiomers

D. A racemic mixture

See Section 4.1.3.

42 What are stereoisomers that are NOT enantiomers called?

Choose one A. Meso compounds

answer.
B. Racemates

C. Diastereoisomers

D. Chiral centers

See Section 4.1.3

43 What are molecules that are non-superimposable mirror images called?

Choose one A. Enantiomers

answer.
 B. Diastereoisomers

C. Meso compounds

D. Racemates

See Section 4.1.3

44 Fill in the blank. An achiral compound having chiral atoms is a(n) __________________.

Choose one A. Chiral compound

answer.
B. Achiral compound

C. Racemic mixture

D. Meso compound

See Section 4.1.3

45 What is a mixture containing equal parts of each enantiomer of a pair called?

Choose one A. An achiral mixture

answer.
B. A stereoisomeric mixture

C. A meso compound

D. A racemate

See Section 4.1.3

46 Which of the following statements about optically active compounds is false?

Choose one A. Racemates are not optically active.

answer.
B. Individual enantiomers are not optically active.

C. Achiral compounds are not optically active.

D. Meso compounds are not optically active.

See Section 4.1.3

47 Which of the following structures is chiral?

Answer:

See Section 4.1.3

Correct answer: C[C@@]1(Cl)CCCC(Br)C1

48 Which of the following carbocations is the most stable?

Answer:

See 4.2.1
Correct answer: CCC[C+](C)C

49
This secondary carbocation, (CH3)3 CC+CH2CH3, rearranges to which of the following tertiary carbocations that is the most
stable?

Answer:

See 4.2.1
Correct answer: CCC(C)[C+](C)C

50 What are the products of the reaction of CH3Br + NaSH?

Choose one A. CH3SH + NaBr

answer.
B. CH3SH only

C. CH3OH + NaBr

D. NaBr only

See Section 4.2.3

51 Why are the functional carbons of organolithium and Grignard reagents effective as reducing agents?

Choose one A. Because they are basic and nucleophilic

answer.
B. Because they are basic and electrophilic

C. Because they are acidic and electrophilic

D. Because they are positively charged

See Section 4.2.6

52 The reaction of 1,2-dibromopentane with magnesium in ether yields which of the following?

Answer:

See Section 4.2.6

Correct answer: C=CCCC

53 What is the molecular structure for 2,2-dimethyl-1-butanol?

Answer:

See section 5.1

Correct answer: CCC(C)(C)CO

54 What is the molecular structure for 1-cyclopenten-1-ol?

Answer:

See Section 5.1

Correct answer: OC1=CCCC1

55
Why are alcohols are much stronger acids than alkanes?
Choose one A. Because both carbon and hydrogen are electrophilic in alcohols
answer.
B. Because the electronegativity of oxygen is substantially greater than that of carbon and
hydrogen

C. Because the covalent bonds of the alcohol functional group are polarized

D. All of the above

See Section 5.2

56 What is the product of the addition of (CH3)2C=CH2 to H20 in the presence of H+ (strong acid)?

Answer:

See Section 5.3

Correct answer: CC(C)(C)O

57 What does the reaction of CH3(CH2)2CH2OH + TsCl with pyridine and then NaBr yield?

Answer:

See Section 5.3

Correct answer: CCCCBr

58 What is the product of the reaction of (CH3)3C(CH2)2 Br with PBr3?

Answer:

See Section 4.3

Correct answer: CC(C)(C)CCBr

59 What is the major product of the reaction of (CH3)3-CH(OH)CH2CH3 plus H3PO4?

Answer:

See Section 5.3

Correct answer: CCC(C)=C(C)C

60 What is the product for the reaction of (CH3)3COH with H3PO4?

Answer:

See Section 5.3

Correct answer: C=C(C)C

61 The products of the reaction of (CH3)2CHCH(OH)CH3 + HBr are H2O and which of the following?

Answer:

See Section 5.3

Correct answer: CCC(C)(C)Br

62 The products of the reaction of (CH3)3CBr + CH3CH2OH are HBr plus which of the following?
Answer:

See Section 5.3

Correct answer: CCOCC(C)(C)C

63 The reaction of 4-hexen-4-methyl-1-ol with PCC in CH2Cl2 yields which of the following?

Answer:

See Section 5.3

Correct answer: CC=C(C)CCC=O

64 What does the reaction of 3-ethyl-cyclohexanol with H2CrO4 and acetone (Jones Reagent) yield?

Answer:

See Section 5.3

Correct answer: CCC1CCCC(=O)C1

65 What is the structure for 3-ethyl-2-pentene?

Answer:

See Section 6.1.1

Correct answer: CC=C(CC)CC

66 What is the structure for trans-3-nonane?

Answer:

See Section 6.1.2

Correct answer: CCC=CCCCCC

67 What is the molecular structure of E-1-bromo-1-chloro-2-methyl-1-butene?

Answer:

See Section 6.1.2

Correct answer: CCC(C)=C(Cl)Br

68 What is the C=C double bond in alkenes made of?

Choose one A. Two pi bonds

answer.
B. One sigma and two pi bonds

C. Two sigma bonds

D. One sigma and one pi bond

See Section 6.1.2.

69 Complete the sentences. Two degrees of unsaturation could be equivalent to all of the following EXCEPT:

Choose one A. One ring and one double bond.

answer.
 B. Two rings and one double bond.

C. Two rings.

D. One triple bond.

70 What is the major alkene product synthesized through the reaction of

2-methyl-2-butanol in the presence of H2SO4 at 80 degrees?

Answer:

See Section 6.2

Correct answer: CC=C(C)C

71 What does the reaction of 1-methyl-1-cyclohexene with H2 gas in the presence of Pd/C yield?

Answer:

See Section 6.2

Correct answer: [H][C@@H]1CCCC[C@@]1([H])C

72 In disubstituted alkenes, why are cis isomers less stable than trans isomers?

Choose one A. Because alkenes have pi bonds

answer.
B. Because of hyperconjugation

C. Because of steric hindrance

D. Because cis isomers typically do not react in reactions

See Section 6.2

73 What is the product of the reaction of 2-methyl-propene with HBr in the presence of H2O2 ?

Answer:

See Section 6.2

Correct answer: CC(C)CBr

74 When the carbene methylene reacts with cis-2-pentene, what are the resulting products?

Answer:

See Section 6.2

Correct answer: CC[C@@H]1C[C@@H]1C

75 The reaction of 2-butene with Br2 in CCl4 yields?

Answer:

See Section 6.2

Correct answer: [H][C@](C)(Br)[C@]([H])(C)Br

76 The reaction of 3,3-dimethyl-1-butene with HCl occurs via the most stable carbocation. What is the product of this reaction?
Answer:

See Section 6.2

Correct answer: [H]C(C)(C)C(C)(C)Cl

77 What is the two-step reaction of 1-methyl-cyclobutene with BH3 and then H2O2 in NaOH and H2O yield?

Answer:

See Section 6.2

Correct answer: CC1CCC1O

78 The reaction of trans-2-hexene with MCPBA CH2Cl2 yields a pair of entantiomers with what formula?

Answer:

See Section 6.2

Correct answer: [H][C@]1(C)O[C@]1([H])CCC

79 What is one of the products of the reaction of 2,3-dimethyl-2-pentene with O3 followed by reductive workup?

Answer:

See Section 6.2

Correct answer: CCC(C)=O

80 Which of the following is NOT a step in the allylic bromination mechanism?

Choose one A. Propagation

answer.
B. Initiation

C. Bromine preparation

D. Termination

See Section 6.2

81 What does the reaction of 1-methyl-1-cyclopentene with Osmium tetroxide in H2S produce?

Answer:

See Section 6.2

Correct answer: [H][C@]1(O)CCC[C@@]1(C)O

82 What is the major product of the reaction of 4-methyl-1-cyclohexane with NBS?

Answer:

See Section 6.2

Correct answer: CC1CC=CC(Br)C1

83 Which of the following statements about hydroboration reactions of alkenes is false?

Choose one A. The reaction is a one-step reaction.

answer.
 B. The geometry of the reaction is syn.

C. It occurs via a carbocation intermediate.

D. It takes place with a retention of configuration.

See Section 6.2

84 At room temperature, alkenes can exist in which of the following phases?

Choose one A. Solids and liquids

answer.
B. Liquids and gases

C. Solids and gases

D. Solids, liquids, and gases

See Section 6.2

85 Which of the following line drawings represents 3-methyl-1-butyne?

Answer:

See Section 7.1

Correct answer: [H]C#CC(C)C

86 What is the correct formula for 1-cyclopentyl-3,3-dimethyl-1-butyne?

Answer:

See Section 7.1

Correct answer: CC(C)(C)C#CC1CCCC1

87 Alkynes are the most acidic hydrocarbon due to which of the following?

Choose one A. sp2 hybridation of the carbons

answer.
B. sp3 hybridation of the carbons

C. sp hybridation of the carbons

D. sp3 d hybridation of the carbons

See Section 7.1

88 The triple bond of alkynes contributes to the which of the following characteristics?

Choose one A. The nonpolar bonding strength

answer.
B. The linear geometry

C. Acidity

D. All of the above

See Section 7.1

89 What is the structure of the alkyne produced produced by the reaction of 2,2-dimethyl-5,6-dichloroheptane with RO-?
Answer:

See Section 7.2

Correct answer: CC#CCCC(C)(C)C

90 What does the reaction of 1,2-dibromopentane with 3 NaNH2 in NH3(l) followed by H2O yield?

Answer:

See Section 7.2

Correct answer: [H]C#CCCC

91 What does the reaction of acetylene with nBuLi in THF and HMPA followed by chloroethane yield?

Answer:

See Section 7.2

Correct answer: [H]C#CCC

92 What is a good starting material to produce 3,3-dimethyl-1-butyne in the lab?

Answer:

See Section 7.2

Correct answer: CC(C)(C)C(Br)CBr

93 What does the reaction of 2-butyne with Lindlar Catalyst yield?

Answer:

See Section 7.2

Correct answer: [H]C(C)=C([H])C

94 What does the reaction of 2-butyne with Lindlar Na/NH3 Catalyst yield?

Answer:

See
Correct answer: [H]C(C)=C([H])C

95 What does the reaction of 3,3-dimethyl-1-butyne with two equivalents of Br2 in a slow reaction yield?

Answer:

See Section 7.2.

Correct answer: CC(C)(C)C(Br)(Br)C(Br)Br

96 The reaction of 3-hexyne with H20, H+ and HgSO4 produces two products in equilibrium with each other. What is the more
stable of the two products?

Answer:

See Section 7.2.

Correct answer: CCCC(=O)CC

97 What does the reaction of 4-cyclopropyl-1-pentyne with BH3 followed by H2O2 in NaOH yield as a final product?

Answer:

Correct answer: CC(CCC=O)C1CC1

98 Alkynes can be oxidized by reacting with KMnO4 in the presence of H2O or ozone to produce carboxylic acids. What does the
oxidation of 3-hexyne in this manner yield?

Answer:

See Section 7.2.

Correct answer: CCC(=O)O

99 What does the reaction of acetylene with 2 NaNH2 in NH3(l) followed by the addition of 2 moles of 1-bromopropane yield?

Answer:

See Section 7.2.

Correct answer: CCCC#CCCC

100 What does the reaction of HC≡C-CH2CH2Br + Mg (in ether) yield?

Answer:

See Section 7.2

Correct answer: CCC#C[MgBr]