1
Which of the following accurately represents the hybridizations for the carbon atoms in C2H6 (ethane), C2H4 (ethene), and C2H2 (ethyne)?

Choose one answer.
A. sp, sp3 and sp2, respectively
B. sp3, sp2, and sp, respectively
C. sp2, sp, and sp3, respectively
D. sp, sp, and sp2, respectively
.
.
Question 2
Which of the following accurately represents the molecular geometry for the carbon atoms in C2H6 (ethane), C2H4 (ethene), and C2H2 (ethyne)?
Choose one answer.
A. Linear, tetrahedral, and planar, respectively
B. Tetrahedral, Linear, and planar, respectively
C. Linear, Linear, and planar, respectively
D. Tetrahedral, planar, and linear, respectively
.
.
Question 3
What are the formal charges on the nitrogen and boron atoms in H3N - BH3, respectively?
Choose one answer.
A. +1, -1
B. +1, +1
C. -1, -1
D. -1, +1
.
.
Question 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 answer.
A. Van der Waals attraction
B. Hydrogen bonding
C. Ionic bonding
D. Covalent bonding
.
.
Question 5

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

Choose one answer.
A. Covalent bond
B. Ionic bond
C. Van der Waals force
D. Hydrogen bond
.
.
Question 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 answer.
A. Exothermic
B. Endothermic
C. Analgesic
D. Endodermic
.
.
Question 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 answer.
A. Trans energy
B. Static energic
C. Kinetic energy
D. Activation energy
.
.
Question 8

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

Choose one answer.
A. Bronsted acids
B. Lowry Bases
C. Bronsted-Lowry Acids
D. Bronsted-Lowry Bases
.
.
Question 9
In general, what is the strongest effect on the acidity of a molecule, even more important than bond strength?
Choose one answer.
A. Anion effect
B. Cation effect
C. Hydrogen effect
D. Hydroxide effect
.
.
Question 10

In a chemical reaction, what is the species that supplies a pair of electrons to form a covalent bond called?
Choose one answer.
A. Lewis acid
B. Hydrogen species
C. Lewis protons
D. Lewis base
.
.
Question 11

The molecular formula CnH2n-2 is the general formula for which group of hydrocarbons?

Choose one answer.
A. Alkanes
B. Alkenes
C. Cycloalkanes
D. Alkynes
.
See Section 2.1
.
Question 12

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

Choose one answer.
A. 2, 4, 6, 7, respectively
B. 2, 6, 4, 7, respectively
C. 4, 2, 7, 6, respectively
D. 2, 7, 6, 4, respectively
.
See Section 2.1
.
Question 13

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

Choose one answer.
A. Elimination
B. Substitution
C. Addition
D. Combustion
.
See Section 2.3
.
Question 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 answer.
A. Elimination
B. Addition
C. Substitution
D. Combusion
.
See Section 2.3
.
Question 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 answer.
A. Elimination
B. Addition
C. Substitution
D. Free radical
.
See Section 2.3
.
Question 16
What is the product of a rearrangement reaction called?
Choose one answer.
A. A free radical
B. A carbocation
C. An isotope
D. An isomer
.
See Section 2.3
.
Question 17

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

Choose one answer.
A. Seven
B. Four
C. Eight
D. One
.
See Section 2.3
.
Question 18

Electrophiles are attracted to which of the following molecules?

Choose one answer.
A. Both NH3 and NH4+
B. Both CH3 O- and NH3
C. Both CH3O- and K +
D. NH3, NH4+, CH3O-, and K +
.

See Section 2.4

.
Question 19

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

Choose one answer.
A. NH4+
B. H3O+
C. NH3
D. CH3OH
.
See Section 2.4.
.
Question 20
A base is defined by its ability to accept which of the following?
    Choose one answer.
    A. An electron
    B. A free radical
    C. A neutron
    D. A proton
    .
    See Section 2.4
    .
    Question 21

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

    Answer:

    .
    See Section 3.1
    Correct answer: CCC(C)CC
    .
    Question 22

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

    Answer:

    .

    See Section 3.1

    Correct answer: CC(C)(C)C1CCCC1
    .
    Question 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
    .
    Question 24
    Which of the followingis the correct formula for sec-butylcyclobutane?
    Answer:

    .
    See Section 3.1
    Correct answer: CCC(C)C1CCC1
    .
    Question 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
    .
    Question 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
    .
    Question 27
    Which of the following statements is true concerning conformations of ethane?
    Choose one answer.
    A. The staggered conformation is the most stable.
    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
    .
    Question 28
    What is the reactivity order of halogens from most reactive to least reactive?
    Choose one answer.
    A. Cl, F, Br, I
    B. Cl, Br, I, F
    C. F, Cl, Br, I
    D. I, Br, Cl, F
    .
    See Section 3.5
    .
    Question 29
    Which of the following is the most stable conformationof ethane?
    Choose one answer.
    A. Anti
    B. Gauche
    C. Eclipsed
    D. Fully eclipsed
    .
    See Section 3.2
    .
    Question 30
    The product of the reaction of CH4 + O2 + heat yields which of the following?
    Choose one answer.
    A. 2 CO2+ 2H2O + heat
    B. CO2+ 2H2O + heat
    C. 2 CO2+ 3H2O + heat
    D. CO2+ 3H2O + heat
    .
    See Section 3.5
    .
    Question 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
    .
    Question 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
    .
    Question 33
    Carbocation intermediates can react further to do which of the following?
    Choose one answer.
    A. Give a substitution product when the cation bonds to a nucleophile
    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
    .
    Question 34
    Complete the sentence: Elimination from 2-iodobutane produces all of the following EXCEPT:
    Answer:

    .
    See Section 4.2.4
    Correct answer: CC=CC
    .
    Question 35
    Complete the sentence. The SN2 mechanism is favored by all of the following, EXCEPT:
    Choose one answer.
    A. Primary alkyl halides
    B. Nonpolar aprotic solvent
    C. Tertiary alkyl halides
    D. Less substituted alkyl halides
    .
    See Section 4.2.3
    .
    Question 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 answer.
    A. SN3
    B. SN1
    C. SN2
    D. E2
    .
    See 4.2.3
    .
    Question 37
    What is the correct molecular structure for isobutylbromide?
    Answer:

    .
    See Section 4.1.1
    Correct answer: CC(C)(C)Br
    .
    Question 38
    What is the molecular structure of 1,2-dibromocyclohexane?
    Answer:

    .
    See Section 4.1.1.
    Correct answer: BrC1CCCCC1Br
    .
    Question 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 answer.
    A. First order
    B. Zero order
    C. Third order
    D. One half order
    .
    See Section 4.2.3
    .
    Question 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 answer.
    A. Constitutional isomers
    B. Stereoisomers
    C. Tautomers
    D. Stable structural isomers
    .
    See Section 4.1.3.
    .
    Question 41
    Which of the following are stereoisomers that are non-superimposable mirror images?
    Choose one answer.
    A. Diastereomers
    B. Meso compounds
    C. Enantiomers
    D. A racemic mixture
    .
    See Section 4.1.3.
    .
    Question 42
    What are stereoisomers that are NOT enantiomers called?
    Choose one answer.
    A. Meso compounds
    B. Racemates
    C. Diastereoisomers
    D. Chiral centers
    .
    See Section 4.1.3
    .
    Question 43
    What are molecules that are non-superimposable mirror images called?
    Choose one answer.
    A. Enantiomers
    B. Diastereoisomers
    C. Meso compounds
    D. Racemates
    .
    See Section 4.1.3
    .
    Question 44
    Fill in the blank. An achiral compound having chiral atoms is a(n) __________________.
    Choose one answer.
    A. Chiral compound
    B. Achiral compound
    C. Racemic mixture
    D. Meso compound
    .
    See Section 4.1.3
    .
    Question 45
    What is a mixture containing equal parts of each enantiomer of a pair called?
    Choose one answer.
    A. An achiral mixture
    B. A stereoisomeric mixture
    C. A meso compound
    D. A racemate
    .
    See Section 4.1.3
    .
    Question 46
    Which of the following statements about optically active compounds is false?
    Choose one answer.
    A. Racemates are not optically active.
    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
    .
    Question 47
    Which of the following structures is chiral?
    Answer:

    .
    See Section 4.1.3
    Correct answer: C[C@@]1(Cl)CCCC(Br)C1
    .
    Question 48
    Which of the following carbocations is the most stable?
    Answer:

    .
    See 4.2.1
    Correct answer: CCC[C+](C)C
    .
    Question 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
    .
    Question 50
    What are the products of the reaction of CH3Br + NaSH?
    Choose one answer.
    A. CH3SH + NaBr
    B. CH3SH only
    C. CH3OH + NaBr
    D. NaBr only
    .
    See Section 4.2.3
    .
    Question 51
    Why are the functional carbons of organolithium and Grignard reagents effective as reducing agents?
    Choose one answer.
    A. Because they are basic and nucleophilic
    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
    .
    Question 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
    .
    Question 53
    What is the molecular structure for 2,2-dimethyl-1-butanol?
    Answer:

    .
    See section 5.1
    Correct answer: CCC(C)(C)CO
    .
    Question 54
    What is the molecular structure for 1-cyclopenten-1-ol?
    Answer:

    .
    See Section 5.1
    Correct answer: OC1=CCCC1
    .
    Question 55

    Why are alcohols are much stronger acids than alkanes?


    Choose one answer.
    A. Because both carbon and hydrogen are electrophilic in alcohols
    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
    .
    Question 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
    .
    Question 57
    What does the reaction of CH3(CH2)2CH2OH + TsCl with pyridine and then NaBr yield?
    Answer:

    .
    See Section 5.3
    Correct answer: CCCCBr
    .
    Question 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
    .
    Question 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
    .
    Question 60
    What is the product for the reaction of (CH3)3COH with H3PO4?
    Answer:

    .
    See Section 5.3
    Correct answer: C=C(C)C
    .
    Question 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
    .
    Question 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
    .
    Question 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
    .
    Question 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
    .
    Question 65
    What is the structure for 3-ethyl-2-pentene?
    Answer:

    .
    See Section 6.1.1
    Correct answer: CC=C(CC)CC
    .
    Question 66
    What is the structure for trans-3-nonane?
    Answer:

    .
    See Section 6.1.2
    Correct answer: CCC=CCCCCC
    .
    Question 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
    .
    Question 68
    What is the C=C double bond in alkenes made of?
    Choose one answer.
    A. Two pi bonds
    B. One sigma and two pi bonds
    C. Two sigma bonds
    D. One sigma and one pi bond
    .
    See Section 6.1.2.
    .
    Question 69
    Complete the sentences. Two degrees of unsaturation could be equivalent to all of the following EXCEPT:
    Choose one answer.
    A. One ring and one double bond.
    B. Two rings and one double bond.
    C. Two rings.
    D. One triple bond.
    .
    .
    Question 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
    .
    Question 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
    .
    Question 72
    In disubstituted alkenes, why are cis isomers less stable than trans isomers?
    Choose one answer.
    A. Because alkenes have pi bonds
    B. Because of hyperconjugation
    C. Because of steric hindrance
    D. Because cis isomers typically do not react in reactions
    .
    See Section 6.2
    .
    Question 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
    .
    Question 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
    .
    Question 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
    .
    Question 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
    .
    Question 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
    .
    Question 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
    .
    Question 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
    .
    Question 80
    Which of the following is NOT a step in the allylic bromination mechanism?
    Choose one answer.
    A. Propagation
    B. Initiation
    C. Bromine preparation
    D. Termination
    .
    See Section 6.2
    .
    Question 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
    .
    Question 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
    .
    Question 83
    Which of the following statements about hydroboration reactions of alkenes is false?
    Choose one answer.
    A. The reaction is a one-step reaction.
    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
    .
    Question 84
    At room temperature, alkenes can exist in which of the following phases?
    Choose one answer.
    A. Solids and liquids
    B. Liquids and gases
    C. Solids and gases
    D. Solids, liquids, and gases
    .
    See Section 6.2
    .
    Question 85
    Which of the following line drawings represents 3-methyl-1-butyne?
    Answer:

    .
    See Section 7.1
    Correct answer: [H]C#CC(C)C
    .
    Question 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
    .
    Question 87
    Alkynes are the most acidic hydrocarbon due to which of the following?
    Choose one answer.
    A. sp2 hybridation of the carbons
    B. sp3 hybridation of the carbons
    C. sp hybridation of the carbons
    D. sp3 d hybridation of the carbons
    .
    See Section 7.1
    .
    Question 88
    The triple bond of alkynes contributes to the which of the following characteristics?
    Choose one answer.
    A. The nonpolar bonding strength
    B. The linear geometry
    C. Acidity
    D. All of the above
    .
    See Section 7.1
    .
    Question 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
    .
    Question 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
    .
    Question 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
    .
    Question 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
    .
    Question 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
    .
    Question 94
    What does the reaction of 2-butyne with Lindlar Na/NH3 Catalyst yield?

    Answer:

    .
    See
    Correct answer: [H]C(C)=C([H])C
    .
    Question 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
    .
    Question 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
    .
    Question 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
    .
    Question 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
    .
    Question 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
    .
    Question 100
    What does the reaction of HC≡C-CH2CH2Br + Mg (in ether) yield?
    Answer:

    .
    See Section 7.2
    Correct answer: CCC#C[MgBr]
    .