Ochem Final Review

Flashcard maker : Lily Taylor
Approximately how long is a C?C single bond of an alkane?
153 pm
What is the approximate C?C?C bond angle in propane?
109┬║
What is the name of the linear hydrocarbon with the molecular formula C7H16?
Heptane
What is the name of the linear hydrocarbon with the molecular formula C11H24?
Undecane
How many hydrogen atoms are there in nonane, the linear hydrocarbon with nine carbon atoms?
20
How many hydrogen atoms are there in dodecane, the linear hydrocarbon with twelve carbon atoms?
26
How many constitutional isomers are there with the molecular formula C4H10?
2
How many constitutional isomers are there with the molecular formula C5H12?
3
How many constitutional isomers are there with the molecular formula C6H14?
3
(Study Review part 1 Questions 10-15,20 for nomenclature)
c:
Which of the following compounds has 1┬░, 2┬░, 3┬░ and 4┬░ carbon atoms?
a. hexane
b. 2-methylhexane
c. 2,2-dimethylhexane
d. 2,2,3-trimethylhexane
D
Which of the following compounds has only 1┬░ and 3┬░ carbon atoms?
a. hexane
b. 2-methylpentane
c. 3-methylpentane
d. 2,3-dimethylbutane
D
Know isobutane and neopentane. (Question 18)
c:
Study Newman projections (Question 21,22,23,)
c:
Which of the following cycloalkanes has the most ring strain?
cyclopropane
cyclobutane
cyclopentane
Cyclohexane
Cyclopropane
Which of the following cycloalkanes has the least ring strain?
cyclopropane
cyclobutane
cyclopentane
Cyclohexane
Cyclohexane
Which of the following alkanes has the highest boiling point?
a. propane
b. butane
c. pentane
d. hexane
D.) Hexane
Which of the following alkanes has the highest boiling point?
a. 2,3-dimethylbutane
b. 2-methylpentane
c. 3-methylpentane
d. hexane
D.) Hexane
Which of the following compounds can adopt a chair conformation in which there are no axial methyl groups?
a. cis-1,2-dimethylcyclohexane
b. cis-1,3-dimethylcyclohexane
c. trans-1,3-dimethylcyclohexane
d. cis-1,4-dimethylcyclohexane
B.) cis-1,3-dimethylcyclohexane
What is the approximate dihedral angle between the two chlorine atoms in cis-1,2-dichlorocyclohexane?
a. 0┬░
b. 60┬░
c. 120┬░
d. 180┬░
B.) 60┬║
What is the approximate dihedral angle between the two chlorine atoms in the diequatorial conformation of trans-1,2-dichlorocyclohexane?
a. 0┬░
b. 60┬░
c. 120┬░
d. 180┬░
B.) 60┬║
Which of the following is NOT true regarding the properties of alkanes?
a. alkanes are nonpolar
b. alkanes burn in air to give H2O and CO2
c. alkanes are highly miscible with water
d. the strongest intermolecular force between alkane molecules is the van der Waals interaction
C.) Alkanes are highly miscible with water
Which of the following statements is not true?
a. Combustion of an alkane is an exothermic reaction.
b. The heat of combustion of propane is three times that of methane.
c. The constitutional isomers of C7H16 have different heats of combustion from one another
d. The products of combustion of an alkane are H2O and CO2.
B
What is the approximate dihedral angle between the two chlorine atoms in the diaxial conformation of trans-1,2-dichlorocyclohexane?
a. 0┬░
b. 60┬░
c. 120┬░
d. 180┬░
D.) 180┬║
Which of the following is the definition of a pair of enantiomers?
a. A pair of structures that are superposable mirror images of one another
b. A pair of stereoisomers that are non-superposable mirror images of one another
c. A pair of stereoisomers that are not mirror images of one another
d. A pair of stereoisomers that have equal specific rotations
B
Which of the following is the definition of a pair of diastereomers?
a. A pair of structures that are superposable mirror images of one another
b. A pair of stereoisomers that are non-superposable mirror images of one another
c. A pair of stereoisomers that are not mirror images of one another
d. A pair of stereoisomers that have equal specific rotations
C
Which of the following is the definition of chirality?
a. The non-superposability of an object on its mirror image
b. The superposability of an object on its mirror image
c. A molecule that has a carbon atom with four different substituents
d. A molecule with a mirror image
C
Which of the following is the definition of a meso compound?
a. A molecule with stereocenter centers which is chiral
b. A molecule with stereocenter centers which is not chiral
c. A diastereomer with no stereocenter centers
d. A chiral compound with more than one stereocenter center
B
Which of the following statements is not true regarding pairs of enantiomers?
a. They have identical melting points
b. They have identical boiling points.
c. They rotate plane polarized light in opposite directions
d. They react at identical rates with chiral reagents
D.) They react at identical rates with chiral reagents
Which of the following statements is true?
a. All mirror images are enantiomers
b. All molecules that have stereocenter centers are chiral
c. Isomers that are not superposable on their mirror images are enantiomers
d. Superposable structural isomers are enantiomers
C
Which of the following compounds is a meso compound?
a. (2R,3R)-dibromobutane
b. (2R,3S)-dibromobutane
c. (2R,3S)-3-bromo-2-butanol
d. (2R,3R)-3-bromo-2-butanol
B
Which of the following statements regarding optical rotation is not true?
a. All (+) enantiomers are dextrorotatory.
b. All R enantiomers are dextrorotatory.
c. All (?) enantiomers rotate plane-polarized light in a counterclockwise direction.
d. All (+) and (?) enantiomers rotate plane-polarized light in opposite directions.
B.) All R enantiomers are dextrorotatory
Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system used in assigning R and S configurations?
a. ?COOH
b. ?CHO
c. ?CH2OH
d. ?CH3
A.) -COOH
Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system used in assigning R and S configurations?
a. ?NH2
b. ?NHCH3
c. ?CH2NH2
d. ?CH2NHCH3
B.) -NHCH3
What is the correct order of the Cahn-Ingold-Prelog ranking of the following substituents as used in assigning R and S configurations of chiral centers? (higher ranking > lower ranking)

1. ?C?CH
2. ?CH2NH2
3. ?NHCH3 4. ?CN

a. 3 > 4 > 2 > 1
b. 4 > 3 > 1 > 2
c. 3 > 4 > 2 > 1
d. 4 > 3 > 2 > 1

c.) 3>4>2>1
What is the correct order of the Cahn-Ingold-Prelog ranking of the following substituents as used in assigning R and S configurations of chiral centers? (higher ranking > lower ranking)

1. ?CH2OH
2. ?CHO
3. ?OCH3
4. ?OCOCH3
a. 3 > 4 > 1 > 2
b. 4 > 3 > 1 > 2
c. 3 > 4 > 2 > 1
d. 4 > 3 > 2 > 1

D.) 4>3>2>1
Which of the following is the correct order of decreasing basicity (stronger base > weaker base)?
a. NH3 > MeNH2 > H2O > HF
b. MeNH2 > NH3 > MeOH > CH4
c. NH3 > Me3N > H2O > MeOH
d. CH3COONa > NaOH > NaOMe > NaNMe2
B.) MeNH2>NH3>MeOH>CH4
Which of the following is the strongest acid?
a. CH3CH3
b. CH3NH2
c. CH3OH
d. CH3F
C.) CH3OH
Which of the following is the strongest acid?
a. HCl
b. HI
c. HF
d. HBr
B.) HI
Which of the following is easiest to deprotonate?
a. CH4
b. CH3CH3
c. CH2=CH2
d. HC?CH
D. HC?CH
Which of the following is the strongest acid?
a. CH3OH
b. CH3CHO
c. CH3COCH3
d. CH3COOH
d. CH3COOH
Which of the following is the strongest acid?
a. CH3NH2
b. CH3PH2
c. CH3OH
d. CH3SH
D.) CH3SH
Which of the following compounds is the strongest acid?
a. HF
b. H2O
c. NH3
d. CH4
a.) HF
Which of the following compounds is the strongest acid?
a. CH3OCH3
b. CH3CH2OH
c. CH3CHO
d. CH3CO2H
D.) CH3CO2H
Which of the following compounds is the strongest acid?
a. CH3COOH
b. ClCH2COOH
c. CH3CH2OH
d. ClCH2CH2OH
B.) ClCH2COOH
Which of the following compounds is the strongest acid?
a. CH3COOH
b. FCH2COOH
c. ClCH2COOH
d. BrCH2COOH
B.) FCH2COOH
Which of the following compounds is the strongest acid?
a. CH4
b. CH3CH3
c. H2C=CH2
d. HC?CH
D.
Which of the following compounds is the strongest acid?
a. CF3OH
b. CF3CH2 CH2OH
c. CF3CH2 CH2 CH2OH
d. CF3CH2 CH2 CH2CH2OH
A.) CF3OH
Which of the following compounds is the strongest acid?
a. CH3CH2CH2COOH
b. CH3CH2CHClCOOH
c. CH3CHClCH2COOH
d. ClCH2CH2CH2COOH
B.) CH3CH2CHClCOOH
Which of the following is the strongest base?
a. NaOH
b. NaCO3
c. H2O
d. CH3OH
a.) NaOH
Which of the following is the strongest base?
a. iodide anion, I?
b. fluoride anion, F?
c. bromide anion, Br?
d. chloride anion, Cl?
B.) F-
Which of the following anions is the strongest base?
a. CH3COO?
b. HO?
c. NH2?
d. Cl?
C.) NH2-
Which of the following anions is the strongest base?
a. NH2?
b. NH3
c. CH3CH=N?
d. CH3C?N
A.) NH2-
Which of the following compounds has the highest pKa?
a. NH3
b. H2O
c. HCl
d. CH4
D.) CH4
Which of the following compounds has the lowest pKa?
a. H2O
b. HBr
c. NH3
d. CH4
B.) HBr
Which of the following terms describes the reactivity of trimethylamine, (CH3)3N?
a. Br├Şnsted-Lowry acid and Lewis acid
b. Br├Şnsted-Lowry base and Lewis base
c. Lewis acid and not a Br├Şnsted-Lowry acid
d. Lewis base and not a Br├Şnsted-Lowry base
B
_________ acids donate protons.
Br├Şnsted-Lowry acid
__________ accept protons.
Br├Şnsted-Lowry base
Which of the following is a Lewis acid but not a Br├Şnsted-Lowry acid?
a. CH3COOH
b. AlCl3
c. H2O
d. CH3OH
B.) AlCl3
Which of the following is a feature of a Lewis acid?
a. proton donor
b. proton acceptor
c. electron pair donor
d. electron pair acceptor
D.) Electron pair acceptor
Which of the following is a feature of a Lewis base?
a. proton donor
b. proton acceptor
c. electron pair donor
d. electron pair acceptor
c.) Electron pair donor
Which of the following is a feature of a Br├Şnsted-Lowry acid?
a. proton donor
b. proton acceptor
c. electron pair donor
d. electron pair acceptor
a.) Proton donor
Which of the following is a feature of a Br├Şnsted-Lowry base?
a. proton donor
b. proton acceptor
c. electron pair donor
d. electron pair acceptor
B.) Proton acceptor
Which of the following has the highest bond dissociation energy?
a. HF
b. HCl
c. HBr
d. HI
A.) HF
Which of the following concepts can be used to rationalize the observation that acetic acid is a stronger acid than methanol?
a. electronegativity
b. resonance
c. valence shell electron pair repulsion theory
d. Pauli exclusion principle
B.) Resonance
H2C=CH-CH3
Which atom is preferentially protonated by a strong acid?
H2C
What is the approximate pKa value of HCl?
a. ?7
b. 5
c. 16
d. 51
A.) -7
What is the approximate pKa value of acetic acid?
a. ?7
b. 5
c. 16
d. 51
B.) 5
Which of the following has a pKa value of approximately 16?
C.) CH3CH2OH
Which of the following statements is not true?
a. The position of the equilibrium for an exergonic reaction favors products
b. The products of an exergonic reaction have a higher Gibbs free energy than the reactants.
c. The equilibrium constant of a reaction for which ?G┬░ = 0 is 1.
d. ?G┬░ = ?H┬░ ? T?S┬░
b. The products of an exergonic reaction have a higher Gibbs free energy than the reactants.
Which of the following is a definition of the rate-determining step of a reaction mechanism?
a. the first step
b. the last step
c. the step that crosses the highest energy barrier
d. the most exothermic step
C.) The step that crosses the highest energy barrier
What is the approximate value of the C?C?C bond angle in propene?
a. 90┬░
b. 109┬░
c. 120┬░
d. 180┬░
c.) 120┬║
What is the approximate value of the H?C?H bonds angle in ethene?
a. 90┬░
b. 109┬░
c. 120┬░
d. 180┬░
c.) 120┬║
What is the approximate value of the length of the carbon-carbon bond in ethene?
a. 121 pm
b. 134 pm
c. 142 pm
d. 154 pm
B.) 134 pm
What is the index of hydrogen deficiency of a compound with a molecular formula of C5H10?
a. 0
b. 1
c. 2
d. 3
B.) 1
What is the index of hydrogen deficiency of a compound with a molecular formula of c6h8?
a. 0
b. 1
c. 2
d. 3
D.) 3
What is the index of hydrogen deficiency of a compound with a molecular formula of c5h9br?
a. 0
b. 1
c. 2
d. 3
B.) 1
What is the index of hydrogen deficiency of a compound with a molecular formula of c6h7Cl?
a. 0
b. 1
c. 2
d. 3
D.) 3
What is the index of hydrogen deficiency of a compound with a molecular formula of C6H15N?
a. 0
b. 1
c. 2
d. 3
A.) 0
What is the index of hydrogen deficiency of a compound with a molecular formula of C6H12N2?
a. 0
b. 1
c. 2
d. 3
C.) 2
Which of the following molecular formulae corresponds to a compound with a hydrogen deficiency of 2?
a. c5h8O2
b. c5h10o
c. C6H15N
d. c5h10br2
A.) C5H8O2
Which of the following does not correspond to a molecular formula of a neutral compound?
a. C5H5Br
b. C5H7Cl2
c. C5H5Br3
d. C5H8Cl4
B.) C5H7Cl2
Which of the following does not correspond to a molecular formula of a neutral compound?
a. c6h9NO2
b. c5h7n2O2
c. c8h12o3
d. C7H7N
B.) C5H7N2O2
Which of the following does not correspond to a molecular formula of a neutral compound?
a. C4H8BrNO
b. c5h9clN2O
c. C7H14BrO3
d. c8h14ClN
C.) C7H14BrO3
Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system used in assigning E and Z configurations of carbon-carbon double bonds?
a. ?CH(CH3)2
b. ?CH2OCH3
c. ?CH2CH3
d. ?CH2Br
D.) -CH2Br
Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system used in assigning E and Z configurations of carbon-carbon double bonds?
a. ?COOH
b. ?Cl
c. ?CH2OH
d. ?CH3
B.) -Cl
How many alkenes have the formula C5H10?
a. 4
b. 5
c. 6
d. 7
C.) 6
How many constitutional isomeric alkenes are there with the formula C6H12?
a. 9
b. 11
c. 12
d. 13
C.) 12
How many isomers of 1,6-heptadiene exist?
a. 1
b. 2
c. 3
d. 4
A.) 1
How many isomers of 1,3-heptadiene exist?
a. 1
b. 2
c. 3
d. 4
B.) 2
How many isomers of 2,4-heptadiene exist?
a. 1
b. 2
c. 3
d. 4
D.) 4
How many isomers of 1,3,5-heptatriene exist?
a. 1
b. 2
c. 4
d. 8
C.) 4
What is the smallest trans cycloalkene that is stable at room temperature?
a. (E) cyclohexene
b. (E) cycloheptene
c. (E) cyclooctene
d. (E) cyclodecene
C
What types of units make up terpenes?
a. isoprene
b. propene
c. vitamin A
d. pentadiene
Isoprene
Which of the following is not true regarding alkenes?
a. alkenes are non polar
b. alkenes burn in air to give H2O and CO2
c. alkenes are highly miscible with water
d. the strongest intermolecular force between alkene molecules is the van der Waals interaction
C.) Alkenes are highly miscible with water
Which of the following compounds is most reactive (least stable)?
a. (Z)-cycloheptene
b. (E)-cycloheptene
c. (Z)-cyclooctene
d. (E)-cyclooctene
B.) (E)-cycloheptene
Which of the following concepts explains why tertiary carbocations are more stable than primary and secondary carbocations?
a. electronegativity
b. resonance
c. hyperconjugation
d. the octet rule
C.) Hyperconjugation
What type of orbitals overlap to provide stability to the tert-butyl carbocation by hyperconjugation?
a. 3┬░ C 2p atomic orbital + 3┬░ C sp2 atomic orbital
b. 3┬░ C 2p atomic orbital + methyl C?H ? molecular orbital
c. 3┬░ C sp2 atomic orbital + methyl C?H ? molecular orbital
d. 3┬░ C 2p atomic orbital + methyl C 2s atomic orbital
b. 3┬░ C 2p atomic orbital + methyl C?H ? molecular orbital
Which of the following concepts explains Markovnikov’s rule as applied to the addition of HBr to propene?
a. the relative stability of carbocations
b. the nucleophilicity of bromide anion
c. the acidity of HBr
d. the Aufbau principle
a. the relative stability of carbocations
What is the correct order of stability of carbocations?
4┬║ > 3┬║ > 2┬║ > 1┬║
T/F? The reagent H2O; H2SO4 follows Markovnikov’s rule and also does rearrangement.
True!
T/F? The reagent BH3; H2O2 does NOT follow Markovnikov’s rule and follows trans-addition.
True!
T/F? Addition of HBr reagent follows Markovnikov’s rule.
True!
T/F? 1. Hg(OAc)2 2. NaBH4 follows Markovnikov’s rule.
True
T/F? In Br2, H2O, Br is added to the less substituted carbon while OH is added to the more substituted carbon. OH follows trans-addition, while Br follows cis-addition.
True
What is the major product obtained upon addition of Br2 to (R)-4-tert-butylcyclohexene?
a. (1R,2R,4R)-1,2-dibromo-4-tert-butylcyclohexane
b. (1S,2R,4R)-1,2-dibromo-4-tert-butylcyclohexane
c. (1S,2S,4R)-1,2-dibromo-4-tert-butylcyclohexane
d. (1S,2S,4S)-1,2-dibromo-4-tert-butylcyclohexane
c.) (1S,2S,4R)-1,2-dibromo-4-tert-butylcyclohexane
T/F? 1. OsO4 2. NaHSO3 H2O adds 2 OH groups to the reactant. Follows cis-addition.
True
T/F? 1. O3 2. (CH3)2S breaks open a cycloalkene.
True
T/F? H2/Pt follows cis-addition.
True
What type of reactive intermediate is formed in the reaction of an alkene with HBr to give a bromoalkane?
a. carbocation
b. carbanion
c. radical
d. cyclic bromonium ion
A.) carbocation
What type of reactive intermediate is formed in the reaction of an alkene with Br2 and water to give a bromohydrin?
a. carbocation
b. carbanion
c. radical
d. cyclic bromonium ion
D.) cyclic bromonium ion
What type of reactive intermediate is formed in the reaction of an alkene with aqueous acid to give an alcohol?
a. carbocation
b. carbanion
c. radical
d. carbene
a.) Carbocation
What type of reaction mechanism accounts for the reaction of an alkene with aqueous acid to give an alcohol?
a. nucleophilic addition
b. electrophilic addition
c. radical addition
d. elimination
b.) Electrophilic addition
What type of reaction mechanism accounts for the reaction of an alkene with HBr to give an alkyl bromide?
a. nucleophilic addition
b. electrophilic addition
c. radical addition
d. elimination
B.) Electrophilic addition
Which of the following reactions of alkenes is not stereospecific?
a. bromination (treatment with Br2 in CHCl3)
b. hydrogenation (treatment with H2/Pt)
c. acid-catalyzed hydration (treatment with aqueous H2SO4)
d. bromohydrin formation (treatment with Br2/H2O)
C.) Acid-catalyzed hydration
Which of the following reactions of alkenes is stereospecific?
a. addition of HCl (treatment with HCl)
b. hydrogenation (treatment with H2/Pt)
c. addition of HBr (treatment with HBr)
d. acid-catalyzed hydration (treatment with aqueous H2SO4)
B.) Hydrogenation
Which of the following reactions of alkenes takes place with anti stereospecificity?
a. bishydroxylation (treatment with OsO4 followed by NaHSO3)
b. hydrogenation (treatment with H2/Pt)
c. addition of HBr (treatment with HBr)
d. bromohydrin formation (treatment with Br2, H2O)
D.) bromohydrin formation
Which of the following reactions of alkenes takes place with syn stereospecificity?
a. addition of bromine (treatment with Br2)
b. hydrogenation (treatment with H2/Pt)
c. addition of HBr (treatment with HBr)
d. acid-catalyzed hydration (treatment with aqueous H2SO4)
B.) Hydrogenation
Approximately how long is a carbon-carbon triple bond of an alkyne?
a. 110 pm
b. 121 pm
c. 135 pm
d. 156 pm
B.) 121 pm
What is the approximate C?C?C bond angle in propyne?
a. 90┬░
b. 109┬░
c. 120┬░
d. 180┬░
D.) 180┬║
How many alkynes are there with the molecular formula C6H10?
a. 4
b. 5
c. 6
d. 7
D.) 7
Which atomic orbitals overlap to form the carbon-carbon triple bond of an alkyne?
a. 2s + 2s; sp + sp; 2p + 2p
b. sp + sp; sp + sp; 2p + 2p
c. sp + sp; 2p + 2p; 2p + 2p
d. sp2 + sp2; sp + sp; 2p + 2p
c
Which atomic orbitals overlap to form the carbon-carbon single bond of 1-propyne?
a. 2s + sp
b. sp + sp2
c. sp + sp3
d. sp2 + sp3
C
What is the smallest cycloalkyne that is stable at room temperature?
a. cyclohexyne
b. cyclononyne
c. cyclododecyne
d. cycloeicosyne
B.) cyclononyne
What is the IUPAC name of the following compound?

CH3CH2CH2?C?C?CH(CH3)2
a. 1-isopropyl-1-pentyne
b. 2-methyl-3-heptyne
c. 6-methyl-4-heptyne
d. isopropyl propyl ethyne

B.) 2-methyl-3-heptyne
What is the IUPAC name of the following compound?

(CH3)2CHCH2?C?C?CH(CH3)2
a. 2,6-dimethyl-3-heptyne
b. 2,6-dimethyl-4-heptyne
c. 1,1,5,5-tetramethyl-2-pentyne
d. 4-nonyne

A.) 2,6-dimethyl-3-heptyne
Which of the following is the strongest acid?
a. propane
b. cyclopropane
c. propene
d. propyne
D.) propyne
Which of the following has the lowest pKa?
a. butane
b. 1-butene
c. 1-butyne
d. 2-butyne
c.) 1-butyne
What is the major organic product obtained from a reaction involving NaNH2; DMSO?
A alkyne or a aldiene.
Which sequence of reactions can be used to convert 1-pentene to 1-pentyne
a. Treatment with HBr; followed by treatment with NaOH
b. Treatment with Br2; followed by treatment with NaNH2
c. Treatment with Br2; followed by treatment with H2SO4
d. Treatment with Br2, H2O; followed by treatment with NaOH
B.) Treatment with Br2; followed by treatment with NaNH2
Which sequence of reactions can be used to convert (Z) 2-pentene to 2-pentyne
a. Treatment with Br2; followed by treatment with NaNH2
b. Treatment with Br2, H2O; followed by treatment with NaOH
c. Treatment with Br2; followed by treatment with H2SO4
d. Treatment with HBr; followed by treatment with NaOH
A.) Treatment with Br2; followed by treatment with NaNH2
What is the major organic product obtained from the following reaction with Br2; CH3COOH, LiBr as the reagent?
CH3-C(triplebond)C-CH3
a. (E) 1,2-dibromobutene
b. (Z) 1,2-dibromobutene
c. (E) 2,3-dibromobutene
d. (Z) 2,3-dibromobutene
C.) (E) 2,3-dibromobutene
What is the major organic product obtained from the following reaction?
CH3-C(triple bond)C-CH3
a. 2,3-dibromobutane
b. 2,2,3,3-tetrabromobutane
c. 2,3-dibromobutene
d. 2,2-dibromobutane
B.) 2,2,3,3-tetrabromobutane
T/F? Addition of HBr to a alkyne follows Markovnikov’s rule.
True
What is the major organic product obtained from the following reaction?
CH3CH2CH2CH2-C(triple bond)C-H
1. BH3
2. H2O2, NaOH

a. 2-hexanone
b. hexanal
c. 2-hexanol
d. cis-2-hexene

B.) Hexanal

-anal for ALL BH3 reactions (including (sia)2BH)

What is the major organic product obtained from the reagents:
1. H2O
2. HgSO4; H2SO4
Ketones (double bond O)
What type of intermediate s formed in the Hg2? catalyzed hydration of an alkyne??
a. an alcohol
b. an enol
c. a 1,2-diene
d. an epoxide
B.) An enol
What happens when H2/Pd is added to an alkyne?
Triple bond is completely broken apart; also breaks other multi-bonds
What happens when 2Na;NH3(l) is added to 2-butyne?
Trans-2-butene
What happens when 1. BH3 2. CH3COOH is added to a reactant?
Cis addition of some kind
What happens when H2;Lindlar catalyst is added to a reactant?
Cis addition of some kind
What is the best choice of reagent(s) to perform:
2,2-dibromopropane –> 2-propyne?
a. H2O; H2SO4
b. 1. 3 moles of NaNH2; 2. H3O+
c. KMnO4, NaOH, H2O
d. Zn
B
Which of the following reagents react with 2-butyne to form (Z)-2-butene

1. H2/Lindlar catalyst
2. (sia)2BH followed by CH3COOH
3. Na/NH3

a. only 1
b. only 2
c. only 3
d. only 1 and 2

D.) Only 1 and 2
Which of the following reagents react with 2-butyne to form butane
a. H2/Lindlar catalyst
b. H2/Pd
c. (sia)2BH followed by CH3COOH
d. Na/NH3
B.) H2/Pd
What is the correct assignment of the names of the following compounds?

1. CH3Cl
2. CH2Cl2
3. CHCl3

a. 1 = methyl chloride; 2 = chloroform; 3 = methylene chloride
b. 1 = trichlor; 2 = chloroform; 3 = methylene chloride
c. 1 = methyl chloride; 2 = methylene chloride; 3 = chloroform
d. 1 = chloroform; 2 = methylene chloride; 3 = trichlor

C
Which of the following has the list of compounds in the correct order of decreasing boiling point (higher boiling point > lower boiling point)?
a. chloromethane > chloroethane > 2-chloropropane > 2-chloro-2-methylpropane
b. 2-chloro-2-methylpropane > 2-chloropropane > chloroethane > chloromethane
c. chloroethane > chloromethane > 2-chloro-2-methylpropane > 2-chloropropane
d. chloromethane > 2-chloro-2-methylpropane > 2-chloropropane > chloroethane
B
Which of the following has the list of compounds in the correct order of decreasing boiling point (higher boiling point > lower boiling point)?
a. 2-fluoropropane > 2-chloropropane > 2-bromopropane > 2-iodopropane
b. 2-chloropropane > 2-iodopropane > 2-fluoropropane > 2-bromopropane
c. 2-iodopropane > 2-chloropropane > 2-fluoropropane > 2-bromopropane
d. 2-iodopropane > 2-bromopropane > 2-chloropropane > 2-fluoropropane
d.2-iodopropane > 2-bromopropane > 2-chloropropane > 2-fluoropropane
Which of the following has the list of compounds in the correct order of decreasing density (higher density > lower density)?
a. CH2Cl2 > CH2Br2 > CH2I2
b. CH2Cl2 > CH2I2 > CH2Br2
c. CH2I2 > CH2Br2 > CH2Cl2
d. CH2I2 > CH2Cl2 > CH2Br2
c. CH2I2 > CH2Br2 > CH2Cl2
Which of the following has the list of compounds in the correct order of decreasing polarity (more polar > less polar)?
a. CCl4 > CHCl3 > CH2Cl2
b. CH2Cl2 > CHCl3 > CCl4
c. CCl4 > CH2Cl2 > CHCl3
d. CHCl3 > CCl4 > CH2Cl2
b. CH2Cl2 > CHCl3 > CCl4
Which of the following has the list of compounds in the correct order of decreasing molecular polar (more polar > less polar)?
a. CH3I > CH3Br > CH3Cl > CH3F
b. CH3F > CH3Cl > CH3Br > CH3I
c. CH3Cl > CH3F > CH3Br > CH3I
d. CH3Cl > CH3I > CH3F > CH3Cl
C.) CH3Cl>CH3F>CH3Br>CH3I
Which of the following bonds has the lowest bond dissociation enthalpy?
a. C?H
b. C?F
c. C?Br
d. C?I
D.) C-I
Which of the following statements is not true?
a. homolytic cleavage of a bond in a neutral molecule gives two radicals
b. radicals have one or more unpaired electrons
c. movement of single electrons is depicted using a “fishhook arrow”
d. the C?F bond is the weakest bond between carbon atom and a halogen
D.) C-F bond is the weakest bond between carbon and a halogen
Which halogen is most useful in the regioselective radical halogenation of alkenes??
a. fluorine
b. chlorine
c. bromine
d. iodine
C.) Bromine
What is the correct order of stability of the following radicals (more stable > less stable)?
1.) 1┬║
2.) 3┬║
3.) 2┬║
2 > 3 > 1
What is the characteristic of a radical chain initiation step?
a. radicals are formed
b. substitution products are formed
c. a radical reacts with a molecule to give a new radical and a new molecule
d. two radicals combine to give a molecule
A.) radicals are formed
What is the characteristic of a radical chain propagation step?
a. radicals are formed
b. byproducts are formed
c. a radical reacts with a molecule to give a new radical and a new molecule
d. two radicals combine to give a molecule
C.) a radical reacts with a molecule to give a new radical and a new molecule
What is the characteristic of a radical chain termination step?
a. radicals are formed
b. substitution products are formed
c. a radical reacts with a molecule to give a new radical and a new molecule
d. two radicals combine to give a molecule
D.) two radicals combine to give a molecule
What type of reactive intermediate is formed in the reaction of propene with N-bromosuccinimide to give 3-bromo-1-propene?
a. allylic carbocation
b. allylic carbanion
c. allylic radical
d. cyclic bromonium ion
C.) allylic radical
What type of reactive intermediate is formed upon irradiation of a solution of toluene (Ph-CH3) and bromine?
a. benzylic carbocation
b. benzylic carbanion
c. benzylic radical
d. cyclic bromonium ion
C.) benzylic radical
Which of the following alkanes does not undergo monobromination to form a single bromoalkane as the major product?
1.) 1-methylcyclohexane
2.) cyclohexane
3.) 2-methylpropane
4.) pentane

a. 1
b. 2
c. 3
d. 4

D.) 4
Which of the following alkenes undergoes allylic bromination to form a single monobrominated product?

1.) Cyclohexene
2.) 2-methyl-2-butene
3.) 1-propene
4.) 2-propene

1.) Cyclohexene
What is the major product formed upon radical bromination of (S) 3-methylhexane?
a. (S) 3-bromo-3-methylhexane
b. (R) 3-bromo-3-methylhexane
c. a mixture of (R) and (S) 3-bromo-3-methylhexane
d. (3R) 1-bromo-3-methylhexane
c. a mixture of (R) and (S) 3-bromo-3-methylhexane
What is the geometry of the central carbon atom of a tert-butyl radical?
a. tetrahedral
b. trigonal planar
c. trigonal pyramidal
d. square planar
B.) Trigonal planar
Which of the following statements is not true about the allyl radical
a. the carbon-carbon bond lengths are identical
b. the unpaired electron density is shared between carbons 1 and 2.
c. it undergoes reaction with bromine to give a single product
d. it is formed by abstraction of a hydrogen atom from the methyl group of propene
B.) The unpaired electron density is shared between carbons 1 and 2
How many electrons does the allyl radical have in p orbitals
a. 1
b. 2
c. 3
d. 4
C.) 3
How many ?-bonding, non-bonding, and antibonding orbitals does the allyl radical possess?
a. one bonding, one nonbonding, and one antibonding
b. two bonding, no nonbonding, and no antibonding
c. two bonding, one nonbonding, and no antibonding
d. three bonding, no nonbonding, and no antibonding
A.) one bonding, one nonbonding, and one antibonding
What type of orbitals overlap to provide stability to the tert-butyl radical by hyperconjugation?
a. 3┬░ C 2p atomic orbital + 3┬░ C sp2 atomic orbital
b. 3┬░ C 2p atomic orbital + methyl C?H ? molecular orbital
c. 3┬░ C sp2 atomic orbital + methyl C?H ? molecular orbital
d. 3┬░ C 2p atomic orbital + methyl C 2s atomic orbital
B
What type of orbital contains the unpaired electron of the tert-butyl radical?
a. s
b. p
c. sp3
d. ?
B.) p
Which of the following is an accurate statement of Hammond’s postulate?
a. the transition state of an exothermic reaction will resemble the starting materials (reactants) more than the product
b. the transition state of an exothermic reaction will resemble the products more than the starting materials (reactants)
c. the transition state of an endothermic reaction will resemble the starting materials (reactants) more than the product
d. the difference in energy between the starting materials (reactants) and transition state controls the rate of a reaction
A.) The transition state of an EXOTHERMIC reaction will resemble the starting materials (reactants) more than the product
Which of the following statements is not true regarding the halogenation of alkanes upon treatment with halogen and light?
a. bromination is more selective for 3┬░ positions than chlorination
b. the reaction proceeds via a radical intermediate
c. the reaction proceeds via a chain reaction
d. this is a useful process for the formation of fluorides, chlorides, bromides and iodides
D.) This is a useful process for the formation of fluorides, chlorides, bromides, and iodides
What type of reactive intermediate is formed in the reaction of propene with hydrogen bromide in the presence of peroxides to give 1-bromopropane?
a. 1┬░ radical
b. 1┬░ carbocation
c. 1┬░ radical
d. 2┬░ radical
D
What is the major product obtained from the reaction of 2-methyl-2-butene with hydrogen bromide in the presence of peroxides?
a. 2,3-dibromo-2-methylbutane
b. 2-bromo-3-methylbutane
c. 2-bromo-2-methylbutane
d. (E)-1-bromo-2-methyl-2-butene
B.) 2-bromo-3-methylbutane
Which of the following statements is not true?
a. Bromine radicals add to the least substituted end of a carbon-carbon double bond of an alkene.
b. The major anti-Markovnikov product obtained upon addition of HBr to alkenes in the presence of a peroxide is formed in a radical termination step.
c. Two radicals combine in radical termination steps.
d. Alkoxy radicals remove a hydrogen atom from HBr to give an alcohol and a bromine atom.
B.) The major anti-Markovnikov product obtained upon addition of HBr to alkenes in the presence of a peroxide is formed in a radical termination step.
Which of the following compounds is most susceptible to autooxidation?
a. propene
b. 1,3-butadiene
c. 1,4-pentadiene
d. 1,5-hexadiene
C.) 1,4 – pentadiene
What is the reactive intermediate in the autooxidation of cyclohexene?
a. an allylic radical
b. a 2┬░ carbocation
c. a carbocation
d. a diene
A.) an allylic radical
What are the major products formed upon treatment of (E) 3-methyl-2-hexene with HBr in the presence of peroxides?

1. (S,S) 2-bromo-3-methylhexane
2. (S,R) 2-bromo-2-methylhexane
3. (R,S) 2-bromo-2-methylhexane
4. (R,R) 2-bromo-2-methylhexane

a. only 1 and 2
b. only 1 and 4
c. only 2 and 3
d. a mixture of 1, 2, 3, and 4

D.) A mixture of 1, 2, 3, 4
What are the major products formed upon treatment of (E) 3-methyl-2-hexene with HBr in the absence of peroxides?

1. (S) 3-bromo-3-methylhexane
2. (R) 3-bromo-2-methylhexane
3. 2-bromo-3-methylhexane

a. only 1
b. only 2
c. a mixture of 1 and 2
d. only 3

D.) Only 3
Which of the following accounts for the anti-Markovnikov regiochemistry of the reaction of an alkene with HBr in the presence of peroxides?
a. the alkene reacts with HBr to give a carbocation
b. the alkene reacts with a bromine atom to give a radical
c. the alkene reacts with a hydrogen atom to give a radical
d. the alkene reacts with peroxide to five an allylic radical
B.) The alkene reacts with a bromine atom to a give a radical
Which of the following reactions corresponds to a substitution?
a. propene ? 1,2-dibromopropane
b. 1-iodopropane ? propene
c. propene ? propane
d. 1-iodopropane ? 1-bromopropane
d. 1-iodopropane ? 1-bromopropane
Which of the following reactions corresponds to a substitution?
a. tert-butanol ? tert-butyl chloride
b. tert-butanol ? 2-methylpropene
c. 3,3-dimethyl-2-butanol ? 2,3-dimethyl-2-butene
d. cyclohexene ? 1,2-dichlorocyclohexane
a. tert-butanol ? tert-butyl chloride
Which of the following statements related to SN1 reactions is not true?
a. The heterolysis of a bond between atoms which do not bear formal charges always produces a cation and an anion
b. The charged carbon atom of a carbocation has a complete octet of valence shell electrons
c. Carbocations are Lewis acids
d. Nucleophiles seek centers of low electron density
b. The charged carbon atom of a carbocation has a complete octet of valence shell electrons
Which of the following statements related to SN1 reactions is not true?
a. The SN1 reaction can be described as a heterolytic bond cleavage followed by nucleophilic attack
b. Carbocations are electrophilic
c. The charged carbon atom of a carbocation has an unfilled valence shell
d. Nucleophiles are Lewis acids
d. Nucleophiles are Lewis acids
What is the equation for the rate of formation of tert-butyl alcohol from the reaction of tert-butyl bromide (t-BuBr) with water by an SN1 mechanism?
a. Rate = k [t-BuBr]
b. Rate = k [t-BuBr][H2O]
c. Rate = k [H2O]
d. Rate = k [t-BuBr]2
a. Rate = k [t-BuBr]
What is the equation for the rate of formation of 1-iodobutane from the reaction of 1-chlorobutane (BuCl) with NaI by an SN2 mechanism?
a. Rate = k [BuCl]
b. Rate = k [BuCl][NaI]
c. Rate = k [NaI]
d. Rate = k [BuCl]2
b. Rate = k [BuCl][NaI]
What is the equation for the rate of formation of 2-methoxypropane, (CH3CH(OCH3)CH3, from the reaction of 2-bromopropane (i-PrBr) with sodium methoxide (NaOCH3)?
a. Rate = k [i-PrBr]
b. Rate = k [i-PrBr]2
c. Rate = k [NaOCH3]
d. Rate = k [i-PrBr][NaOCH3]
d. Rate = k [i-PrBr][NaOCH3]
What is the equation for the rate of formation of 2-methoxypropane, CH3CH(OCH3)CH3, from the reaction of 2-bromopropane (i-PrBr) with methanol?
a. Rate = k [i-PrBr]
b. Rate = k [i-PrBr]2
c. Rate = k [CH3OH]
d. Rate = k [i-PrBr][CH3OH]
a. Rate = k [i-PrBr]
The reaction of methyl iodide with sodium azide, NaN3, proceeds by an SN2 mechanism. What is the effect of doubling the concentration of NaN3 on the rate of the reaction?
a. the rate remains the same
b. the rate decreases by a factor of 2
c. the rate increases by a factor of 2
d. the rate increases by a factor of 4
c. the rate increases by a factor of 2
The reaction of 1-bromopropane with sodium iodide gives 1-iodopropane. What is the effect of doubling the concentration of NaI on the rate of the reaction?
a. the rate remains the same
b. the rate decreases by a factor of 2
c. the rate increases by a factor of 2
d. the rate increases by a factor of 4
c. the rate increases by a factor of 2
The reaction of tert-butyl bromide, (CH3)3CBr, with methanol in an inert solvent proceeds by an SN1 mechanism to give tert-butyl methyl ether, (CH3)3COCH3. What is the effect of doubling the concentration of methanol on the rate of the reaction?
a. the rate remains the same
b. the rate decreases by a factor of 2
c. the rate increases by a factor of 2
d. the rate increases by a factor of 4
A
The reaction of tert-butyl chloride, (CH3)3CCl, with water in an inert solvent gives tert-butyl alcohol, (CH3)3COH. What is the effect of doubling the concentration of water on the rate of the reaction?
a. the rate remains the same
b. the rate decreases by a factor of 2
c. the rate increases by a factor of 2
d. the rate increases by a factor of 4
a. the rate remains the same
Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium azide, NaN3?
a. 1-fluorohexane
b. 1-chlorohexane
c. 1-bromohexane
d. 1-iodohexane
d. 1-iodohexane
Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium cyanide, NaCN?
a. methyl iodide
b. ethyl iodide
c. 2-iodopropane
d. tert-butyl iodide
a. methyl iodide
Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium methylthiolate, NaSMe?
a. methyl iodide
b. ethyl iodide
c. 2-bromopropane
d. tert-butyl chloride
a. methyl iodide
Which of the following alkyl halides undergoes the fastest solvolysis reaction with formic acid, HCOOH?
a. tert-butyl fluoride
b. tert-butyl chloride
c. tert-butyl bromide
d. tert-butyl iodide
d. tert-butyl iodide
Which of the following alkyl halides undergoes the fastest solvolysis reaction with methanol, CH3OH?
a. methyl chloride
b. ethyl chloride
c. 2-chloropropane
d. tert-butyl chloride
d. tert-butyl chloride
Which of the following alkyl halides undergoes the fastest solvolysis reaction with ethanol, CH3CH2OH?
a. methyl fluoride
b. ethyl bromide
c. 2-chloropropane
d. tert-butyl bromide
d. tert-butyl bromide
Which of the following is best set of conditions for the preparation of tert-butanol?
a. tert-butyl fluoride in water
b. tert-butyl bromide in water
c. tert-butyl fluoride and NaOH in DMSO
d. tert-butyl bromide and NaOH in DMSO
b. tert-butyl bromide in water
Which of the following is the best set of conditions for the preparation of tert-butyl methyl ether?
a. tert-butyl fluoride and NaOCH3 in CH3OH
b. methanol and sodium tert-butoxide in tert-butanol
c. fluoromethane and sodium tert-butoxide in tert-butanol
d. tert-butyl bromide and CH3OH
d. tert-butyl bromide and CH3OH
What is the major product formed upon treatment of (R) 1-bromo-4-methylhexane with sodium cyanide?
a. (R) 1-cyano-4-methylhexane
b. (S) 1-cyano-4-methylhexane
c. (R) 4-methyl-1-hexene
d. (S) 4-methyl-1-hexene
a. (R) 1-cyano-4-methylhexane
What is the major product formed upon treatment of (R) 2-bromohexane with sodium cyanide?
a. (R) 2-cyanohexane
b. (S) 2-cyanohexane
c. 1-hexene
d. 2-hexene
(S) 2-cyanohexane
In which of the following solvents would the reaction of 1-bromobutane with sodium azide, NaN3, proceed the fastest?
a. acetic acid
b. ethanol
c. water
d. acetonitrile
d. acetonitrile
Which of the following solvents is the best choice for the reaction of 1-chlorohexane with sodium bromide?
a. dimethylsulfoxide
b. water
c. hexane
d. toluene, PhCH3
a. dimethylsulfoxide
Which of the following solvents is the best choice for the reaction of 1-chlorohexane with sodium bromide?
a. water
b. N,N-dimethylformamide
c. hexane
d. toluene, PhCH3
b. N,N-dimethylformamide
Which of the following anions is the most nucleophilic in polar protic solvents?
a. F?
b. Cl?
c. Br?
d. I?
d. I?
Which of the following anions is the most nucleophilic in polar aprotic solvents?
a. F?
b. Cl?
c. Br?
d. I?
a. F?
Which of the following compounds is the most nucleophilic in polar protic solvents?
a. H2O
b. NH3
c. H2S
d. PH3
d. PH3
Which of the following is the most nucleophilic?
a. sodium ethoxide
b. acetic acid
c. methanol
d. water
a. sodium ethoxide
Which of the following anions is the best leaving group in an SN1 reaction?
a. F?
b. HO?
c. NH2?
d. Cl?
d. Cl?
Which of the following is the best leaving group in an SN2 reaction?
a. F?
b. H3C?
c. CH3O2SO?
d. HO?
c. CH3O2SO?
Which of the following statements is true regarding the reactivity of 1 and 2 with potassium tert-butoxide?
a. 1 reacts faster than 2
b. 1 and 2 give different dehydrochlorinated products
c. 2 reacts by elimination whereas 1 reacts by substitution
d. 1 reacts by elimination whereas 2 reacts by substitution
a. 1 reacts faster than 2
Which of the following statements is not true regarding the SN2 reaction of (R)-2-bromobutane with sodium cyanide?
a. the reaction proceeds with inversion of configuration
b. the rate is proportional to the concentration of sodium cyanide
c. the rate is proportional to the concentration of (R)-2-bromobutane
d. the rate of the reaction is independent of the identity of the solvent
d. the rate of the reaction is independent of the identity of the solvent
Which of the following statements is true regarding the reaction of tert-butyl bromide with water?
a. the rate is proportional to the concentration of tert-butyl bromide
b. the rate is proportional to the concentration of water
c. the rate is independent of the identity of the solvent
d. the rate of the reaction is independent of the temperature
a. the rate is proportional to the concentration of tert-butyl bromide
Which of the following is not a characteristic of SN2 reactions?
a. the electrophilic carbon undergoes inversion of stereochemistry
b. the rate is proportional to the concentration of substrate
c. the rate is proportional to the concentration of nucleophile
d. the rate is independent of the solvent
d. the rate is independent of the solvent
Which of the following is not a characteristic of SN1 reactions?
a. the electrophilic carbon undergoes inversion of stereochemistry
b. the rate is proportional to the concentration of substrate
c. the reaction proceeds faster in a more polar solvent
d. the rate is independent of the concentration of nucleophile
a. the electrophilic carbon undergoes inversion of stereochemistry
What is the role of tetrabutylammonium chloride as a phase transfer catalyst in the reaction of 1-chlorooctane and sodium cyanide in a mixture of water and CH2Cl2?
a. it transfers 1-chlorooctane into the aqueous phase
b. it transfers cyanide anion into the organic phase
c. it makes water and dichloromethane miscible
d. it transfers the sodium cation into the organic phase
b. it transfers cyanide anion into the organic phase
Which of the following statements is not true regarding SN2 reactions?
a. A carbocation intermediate is formed.
b. The mechanism has only one step.
c. Aprotic solvents are good choices for SN1 reactions.
d. The stereochemical outcome is inversion at the carbon bearing the leaving group.
a. A carbocation intermediate is formed.
Which of the following statements is not true regarding SN1 reactions?
a. A carbocation intermediate is formed.
b. The mechanism has only one step.
c. Polar, protic solvents are good choices for SN1 reactions.
d. The stereochemical outcome is racemization at the carbon bearing the leaving group.
b. The mechanism has only one step.
How many steps does SN1 occur in?
2 steps
How many steps does SN2 occur in?
1 step
How many steps does an E2 reaction occur in?
1 step
How many steps does an E1 reaction occur in?
2 steps
Which of the following sets consists of only polar aprotic solvents?
a. water, hexane, methanol
b. acetic acid, DMF, toluene
c. DMSO, ethanol, acetonitrile
d. DMF, acetonitrile, DMSO
d. DMF, acetonitrile, DMSO
Which of the following sets consists of only polar protic solvents?
a. water, DMF, DMSO
b. acetic acid, methanol, water
c. DMSO, ethanol, acetonitrile
d. DMF, acetonitrile, DMSO
b. acetic acid, methanol, water
Which of the following most favors elimination rather substitution in a reaction with 2-bromopropane?
a. sodium methoxide
b. sodium ethoxide
c. sodium isoproxide
d. sodium tert-butoxide
d. sodium tert-butoxide
Which of the following most favors elimination rather substitution in a reaction with sodium methoxide?
a. bromomethane
b. bromoethane
c. 1-bromopropane
d. 2-bromopropane
d. 2-bromopropane
What is the approximate C?O?H bond angle of an alcohol?
a. 90┬░
b. 109.5┬░
c. 120┬░
d. 180┬░
b. 109.5┬░
What is the approximate C?C?O bond angle of ethanol?
a. 90┬░
b. 109.5┬░
c. 120┬░
d. 180┬░
b. 109.5┬░
Know how to distinguish primary and secondary alcohols.
C:
Which of the following has the highest boiling point?
a. pentane
b. methyl propyl ether
c. diethyl ether
d. 1-butanol
d. 1-butanol
Which of the following has the highest boiling point?
a. 1-butanol
b. 2-butanol
c. tert-butyl alcohol
d. 1,4-butanediol
d. 1,4-butanediol
What is the approximate pKa value of ethanol?
a. ?5
b. 5
c. 16
d. 25
c. 16
Which of the following best describes the reaction of sodium metal with methanol to give hydrogen and sodium methoxide?
a. Lewis acid-base
b. Br├Şnsted-Lowry acid-base
c. electrophile-nucleophile
d. oxidation-reduction
d. oxidation-reduction
What is the major organic product obtained from the reaction of 1-butanol with aqueous HBr at reflux?
a. 1-bromobutane
b. 2-bromobutane
c. 2-bromo-1-butanol
d. 1-butene
a. 1-bromobutane
What is the major organic product obtained from the reaction of 2,2-dimethyl-1-propanol aqueous HBr at reflux?
a. 1-bromo-2,2-dimethylpropane
b. 1-bromo-2-methylbutane
c. 2-bromo-2-methylbutane
d. 3-bromo-2-methylbutane
c. 2-bromo-2-methylbutane
Which of the following alcohols reacts fastest with HBr to give the corresponding alkyl bromide?
a. methanol
b. ethanol
c. 2-propanol
d. 2-methyl-2-propanol
d. 2-methyl-2-propanol
What type of reactive intermediate is formed in the reaction of 2-methyl-2-hexanol with HBr to give 2-bromo-2-methylhexane?
a. an alkoxide
b. a tertiary cation
c. a tertiary radical
d. a tertiary anion
b. a tertiary cation
What is the major organic product obtained upon heating a mixture of 2-methylcyclopentanol and 85% H3PO4?
a. 1-methylcyclopentene
b. 3-methylcyclopentene
c. 4-methylcyclopentene
d. methylenecyclopentene
a. 1-methylcyclopentene
What is the major organic product obtained upon heating a mixture of 3,3-dimethyl-2-butanol, (CH3)3CCH(OH)CH3, with sulfuric acid?
a. 3,3-dimethyl-1-butene
b. 2,3-dimethyl-1-butene
c. 2,3-dimethyl-2-butene
d. tert-butyl alcohol
c. 2,3-dimethyl-2-butene
What is the major organic product obtained upon heating a mixture of 2-butanol and 85% H3PO4?
a. 1-butene
b. cis-2-butene
c. trans-2-butene
d. 2-methylpropene (isobutylene)
c. trans-2-butene
Which of the following alcohols undergoes the most rapid dehydration upon treatment with H2SO4 to give an alkene?
a. methanol
b. ethanol
c. 2-propanol
d. 2-methyl-2-propanol
d. 2-methyl-2-propanol
In a reaction with CrO3, a primary alcohol becomes a ___________ ______.
carboxylic acid
In a reaction with CrO3, a secondary alcohol becomes a _________.
ketone
In a reaction with PCC, a primary alcohol becomes __________.
aldehyde
In a reaction with PCC, a secondary alcohol becomes a __________.
ketone
What type of reactive intermediate is formed in the reaction of tert-butyl alcohol with HCl to give tert-butyl chloride?
a. tert-butyl radical
b. tert-butyl anion
c. tert-butyl cation
d. tert-butoxide
c. tert-butyl cation
What type of reactive intermediate is formed in the reaction of tert-butyl alcohol with H2SO4 to give methylpropene?
a. tert-butyl cation
b. tert-butyl anion
c. tert-butyl radical
d. tert-butoxide
a. tert-butyl cation
What defines an ether?
An oxygen bonded to two other carbons
What defines an epoxide?
“Just the triangle thingy, it usually has an R group attached it. You usually yeah Idk” – Maryam
Triangle = _________
oxirane
Square = _________
oxetane
Pentagon = __________
oxolane
Hexagon = __________
oxane
Thiols have ______.
-SH
Which of the following statements are true?

1. ethanol is more soluble in water than dimethyl ether
2. ethanol has a higher boiling point than dimethyl ether
3. ethanol has the same molecular weight as dimethyl ether

a. only 1
b. only 1 and 2
c. only 1 and 3
d. 1, 2 and 3

d. 1, 2 and 3
What is the IUPAC name of the following compound?

a. ethyl isopropyl thiol
b. 2-ethylsulfanylpropane
c. ethyl isopropyl disulfide
d. isopropylsufanylethane

b. 2-ethylsulfanylpropane
Which of the following reactions provides anisole (PhOCH3) in a high yield?
a. phenol + sodium methoxide
b. bromobenzene + bromomethane
c. sodium phenoxide (PhONa) + bromomethane
d. bromobenzene + sodium methoxide
c. sodium phenoxide (PhONa) + bromomethane
Which of the following reactions provides tert-butyl methyl ether in a high yield?
a. potassium tert-butoxide + iodomethane
b. sodium methoxide + tert-butyl bromide
c. methanol + tert-butyl alcohol in the presence of KOH
d. iodomethane + tert-butyl bromide in the presence of KOH
a. potassium tert-butoxide + iodomethane
Which of the following ethers cannot be prepared by a Williamson ether synthesis?
a. tert-butyl phenyl ether
b. isopropyl methyl ether
c. anisole
d. tert-butyl methyl ether
a. tert-butyl phenyl ether
What type of reactive intermediate is formed in the reaction of tert-butyl methyl ether with HBr to give tert-butyl bromide?
a. tert-butyl anion
b. tert-butoxide
c. tert-butyl radical
d. tert-butyl cation
d. tert-butyl cation
What type of mechanism accounts for the cleavage of dibutyl ether upon treatment with HBr to give two moles of 1-bromobutane?
a. SN1
b. SN2
c. E1
d. E2
b. SN2
What type of mechanism accounts for the cleavage of tert-butyl methyl ether upon treatment with HBr?
a. SN1
b. SN2
c. E1
d. E2
a. SN1
What are the major products obtained upon treatment of anisole, PhOCH3, with excess HBr?
a. phenol and methanol
b. bromobenzene and bromomethane
c. phenol and bromomethane
d. bromobenzene and methanol
c. phenol and bromomethane
What are the major products obtained upon treatment of tert-butyl methyl ether with excess HBr?
a. tert-butyl alcohol and methanol
b. tert-butyl bromide and methanol
c. tert-butyl alcohol and bromomethane
d. tert-butyl bromide and bromomethane
d. tert-butyl bromide and bromomethane
What type of reactive intermediate is formed in the reaction of methyl propene with methanol in the presence of an acid catalyst to give methyl tert-butyl ether (MTBE)?
a. tert-butyl cation
b. tert-butyl radical
c. tert-butyl anion
d. tert-butoxide
a. tert-butyl cation
Which of the following general structures can be made by sequential reaction of epichlorohydrin with appropriate nucleophiles?
C.) 3

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