Exam 3 Multiple Choice Questions Flashcards
Which reaction has only one transition state linking overall reactants with overall products?
A) HBr with cyclopentanol
B) 3-bromopentane with KOC(CH3)3 in (CH3)3COH
C) (S)-2,2-dimethylcyclohexanol heated with concentrated H2SO4
B) 3-bromopentane with KOC(CH3)3 in (CH3)3COH
Which reaction with sodium azide is faster?
A) Cyclohexyl bromide in DMSO
B) Cyclohexyl p-toluenesulfonate in DMSO
B) Cyclohexyl p-toluenesulfonate in DMSO
The reaction of (R)-2-bromopentane with KOC(CH3)3 in (CH3)3COH gives the major product that is formed via which one of the following mechanisms? A) SN1 B) SN2 C) E1 D) E2
D) E2
Which one of the following is thermodynamically more stable?
A) (E)-Cyclotetradecene
B) (Z)-Cyclotetradecene
A) (E)-Cyclotetradecene
Which reacts faster with NaI in Acetone?
A) Cis-1-bromo-3-methyl-cyclopentane
B) 2-bromo-1,1-dimethylcyclopentane
A) Cis-1-bromo-3-methyl-cyclopentane
Which reaction with NaSCH3 is slower?
A) (R)-2-bromopentane in DMSO
B) (R)-2-bromopentane in ethanol
B) (R)-2-bromopentane in ethanol
Which substrate reacts faster via an SN1 Mechanism?
A) (R)-2-bromo-3-methylbutane
B) (R)-2-bromo-2,3-dimethylbutane
B) (R)-2-bromo-2,3-dimethylbutane
Which reacts faster with NaI in Acetone?
A) Cis-1-bromo-3-methylcyclopentane
B) 1-bromo-1-methylcyclopentane
A) Cis-1-bromo-3-methylcyclopentane
Which reaction with NaSCH3 is slower?
A) (R)-2-chloropentane in DMSO
B) (R)-2-bromopentane in DMSO
A) (R)-2-chloropentane in DMSO
Which type of solvent is formic acid best described as?
A) Nonpolar
B) Polar Protic
C) Polar Aprotic
B) Polar Protic
Which reacts faster with sodium azide in dimethyl sulfoxide?
A) 1-iodopentane
B) Pentyl p-toluenesulfonate
B) Pentyl p-toluenesulfonate
Which substrate reacts faster via an SN2 Mechanism?
A) Trans-1-bromo-3-methylcyclohexane
B) Trans-1-(bromomethyl)-3-methylcyclohexane
B) Trans-1-(bromomethyl)-3-methylcyclohexane
Which type of solvent is acetonitrile best described as?
A) Nonpolar
B) Polar Protic
C) Polar Aprotic
C) Polar Aprotic
Which reaction has only one transition state linking overall reactants with overall products?
A) PBr3 with cyclopentanol
B) (R)-2-bromobutane with KOC(CH3)3 in (CH3)3COH
C) 1-methylcyclopentanol heated with concentrated H2SO4
B) (R)-2-bromobutane with KOC(CH3)3 in (CH3)3COH
Does the reaction of (R)-2-bromopentane with NaSH occur faster in…
A) Dimethyl sulfoxide
B) Ethanol
A) Dimethyl sulfoxide
When 1-propanol is added to water, 1-propanol is…
A) Top layer
B) Bottom layer
C) Neither top or bottom because it is miscible with water
C) Neither top of bottom because it is miscible with water
Which reaction with sodium azide is faster?
A) Cyclohexyl bromide in DMSO
B) Cyclohexyl chloride in DMSO
A) Cyclohexyl bromide in DMSO
The reaction of 1-bromopentane with NaOCH3 in CH3OH gives the major product that is formed via which one of the following mechanisms? A) SN1 B) SN2 C) E1 D) E2
B) SN2
Which one of the following is thermodynamically more stable?
A) (E)-Cyclononene
B) (Z)-Cyclononene
B) (Z)-Cyclononene
Which reaction is not a concerted reaction?
A) Bromocyclopentane with NaI in Acetone
B) 3-Bromopentane with NaOCH3 in CH3OH
C) (R)-2,2-dimethylcyclopentanol heated with concentrated H2SO4
C) (R)-2,2-dimethylcyclopentanol heated with concentrated H2SO4
Does the reaction of (R)-2-bromopentane with NaN3 occur faster in…
A) Dimethyl sulfoxide
B) Ethanol
A) Dimethyl Sulfoxide
When 1-hexanol is added to water, the 1-hexanol is…
A) Top layer
B) Bottom layer
C) Neither the top nor bottom layer because it is miscible with water
A) Top layer
Which reaction with sodium iodide in acetone is faster?
A) Cyclohexyl bromide
B) Cyclohexyl p-toluenesulfonate
B) Cyclohexyl p-toluenesulfonate
THe reaction of (R)-2-bromopentane with KOC(CH3)3 in (CH3)3COH gives the major product that is formed via which one of the following mechanisms? A) SN1 B) SN2 C) E1 D) E2
D) E2
Which one of the following is thermodynamically less stable?
A) (E)-Cyclotetradecene
B) (Z)-Cyclotetradecene
B) (Z)-Cyclotetradecene
Which one of the following is soluble in acetone? A) Sodium chloride B) Sodium bromide C) Sodium Iodide D) Sodium p-toluenesulfonate
C) Sodium Iodide
Which one has the larger heat of hydrogenation?
A) (Z)-hex-3-ene
B) 2-methylpent-2-ene
A) (Z)-hex-3-ene
Which one has the smaller heat of combustion?
A) (E)-Cyclooctene
B) (Z)-Cyclooctene
B) (Z)-Cyclooctene
Which one is not a stereoselective reaction?
A) Addition of H2 to 1,2-dimethylcyclopentene with a Pt catalyst
B) Addition of Cl2 and H2O to 1-methylcyclohexene
C) Addition of DBr to 1-methylcyclohexene
C) Addition of DBr to 1-methylcyclohexene
Which one is thermodynamically more stable?
A) 2-methylcyclopentyl cation
B) 1-methylcyclopentyl cation
B) 1-methylcyclopentyl cation
Which one of the following alkenes is expected to give a single constitutional isomer as the major product from its reaction with Br2 and H2O?
A) 4-methylcyclohexene
B) 3-methylcyclohexene
C) 1-methylcyclohexene
C) 1-methylcyclohexene
Acid-catalyzed hydration of 2-methylpent-2-ene gives which of the following types of alcohol as the major product? A) Primary B) Secondary C) Tertiary D) Quaternary
C) Tertiary
The major product of the reaction of trans-2-methylcyclohexanol with PBr3 is which of the following?
A) Trans-1-bromo-2-methylcyclohexane
B) Cis-1-bromo-2-methylcyclohexane
C) 1-bromo-1-methylcyclohexane
B) Cis-1-bromo-2-methylcyclohexane
In connection with electrophilic additions to alkenes, the regioselectivity of the reaction can be understood from a consideration of which one of the following? A) Hund's Rule B) Markovnikov's Rule C) Zaitsev's Rule D) The Cahn-Ingold Prelog Priority Rule
B) Markovnikov’s Rule
Which one has the smaller heat of hydrogenation?
A) (E)-pent-2-ene
B) Pent-1-ene
A) (E)-pent-2-ene
Which one has the larger heat of combustion?
A) (E)-Cyclooctene
B) (Z)-Cyclooctene
A) (E)-Cyclooctene
Which one is a regioselective reaction?
A) Reaction of Cl2 and H2O with 2-methylpent-2-ene
B) Addition of HBr to (E)-but-2-ene
C) Addition of H2 to 2-methylpent-2-ene with a Pt catalyst
A) Reaction of Cl2 and H2O with 2-methylpent-2-ene
Which one has the smaller heat of hydrogenation?
A) Cyclononyne
B) Cyclodecyne
B) Cyclodecyne
Which one of the following alkenes is expected to be the major product from the reaction of 1-bromo-1-methylcyclohexane with NaOCH3 in CH3OH? A) 1-methylcyclohexene B) (R)-2-methylcyclohexene C) (S)-2-methylcyclohexene D) Methylenecyclohexane
A) 1-methylcyclohexene
Hydroboration-oxidation of 1-methylcyclopentene gives which one of the following types of alcohol as the major product? A) Primary B) Secondary C) Tertiary D) Quaternary
B) Secondary
The major product of the reaction of trans-2-methylcyclohexanol with p-toluenesulfonyl chloride and pyridine which of the following…
A) Trans-2-methylcyclohexyl p-toluenesulfonate
B) Cis-2-methylcyclohexyl p-toluenesulfonate
C) Cis-1-chloro-2-methylcyclohexane
A) Trans-2-methylcyclohexyl p-toluenesulfonate
In connection with acid-catalyzed hydration of alkenes, the regioselectivity of the reaction can be understood from a consideration of which one of the following? A) Hund's Rule B) Markovnikov's Rule C) Zaitsev's Rule D) The Cahn-Ingold Prelog Priority Rule
C) Zaitsev’s Rule
