Exam 3 Multiple Choice Questions

Question 1

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

Answer 1

B) 3-bromopentane with KOC(CH3)3 in (CH3)3COH

Question 2

Which reaction with sodium azide is faster?
A) Cyclohexyl bromide in DMSO
B) Cyclohexyl p-toluenesulfonate in DMSO

Answer 2

B) Cyclohexyl p-toluenesulfonate in DMSO

Question 3

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

Answer 3

D) E2

Question 4

Which one of the following is thermodynamically more stable?
A) (E)-Cyclotetradecene
B) (Z)-Cyclotetradecene

Answer 4

A) (E)-Cyclotetradecene

Question 5

Which reacts faster with NaI in Acetone?
A) Cis-1-bromo-3-methyl-cyclopentane
B) 2-bromo-1,1-dimethylcyclopentane

Answer 5

A) Cis-1-bromo-3-methyl-cyclopentane

Question 6

Which reaction with NaSCH3 is slower?
A) (R)-2-bromopentane in DMSO
B) (R)-2-bromopentane in ethanol

Answer 6

B) (R)-2-bromopentane in ethanol

Question 7

Which substrate reacts faster via an SN1 Mechanism?
A) (R)-2-bromo-3-methylbutane
B) (R)-2-bromo-2,3-dimethylbutane

Answer 7

B) (R)-2-bromo-2,3-dimethylbutane

Question 8

Which reacts faster with NaI in Acetone?
A) Cis-1-bromo-3-methylcyclopentane
B) 1-bromo-1-methylcyclopentane

Answer 8

A) Cis-1-bromo-3-methylcyclopentane

Question 9

Which reaction with NaSCH3 is slower?
A) (R)-2-chloropentane in DMSO
B) (R)-2-bromopentane in DMSO

Answer 9

A) (R)-2-chloropentane in DMSO

Question 10

Which type of solvent is formic acid best described as?
A) Nonpolar
B) Polar Protic
C) Polar Aprotic

Answer 10

B) Polar Protic

Question 11

Which reacts faster with sodium azide in dimethyl sulfoxide?
A) 1-iodopentane
B) Pentyl p-toluenesulfonate

Answer 11

B) Pentyl p-toluenesulfonate

Question 12

Which substrate reacts faster via an SN2 Mechanism?
A) Trans-1-bromo-3-methylcyclohexane
B) Trans-1-(bromomethyl)-3-methylcyclohexane

Answer 12

B) Trans-1-(bromomethyl)-3-methylcyclohexane

Question 13

Which type of solvent is acetonitrile best described as?
A) Nonpolar
B) Polar Protic
C) Polar Aprotic

Answer 13

C) Polar Aprotic

Question 14

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

Answer 14

B) (R)-2-bromobutane with KOC(CH3)3 in (CH3)3COH

Question 15

Does the reaction of (R)-2-bromopentane with NaSH occur faster in…
A) Dimethyl sulfoxide
B) Ethanol

Answer 15

A) Dimethyl sulfoxide

Question 16

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

Answer 16

C) Neither top of bottom because it is miscible with water

Question 17

Which reaction with sodium azide is faster?
A) Cyclohexyl bromide in DMSO
B) Cyclohexyl chloride in DMSO

Answer 17

A) Cyclohexyl bromide in DMSO

Question 18

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

Answer 18

B) SN2

Question 19

Which one of the following is thermodynamically more stable?
A) (E)-Cyclononene
B) (Z)-Cyclononene

Answer 19

B) (Z)-Cyclononene

Question 20

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

Answer 20

C) (R)-2,2-dimethylcyclopentanol heated with concentrated H2SO4

Question 21

Does the reaction of (R)-2-bromopentane with NaN3 occur faster in…
A) Dimethyl sulfoxide
B) Ethanol

Answer 21

A) Dimethyl Sulfoxide

Question 22

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

Answer 22

A) Top layer

Question 23

Which reaction with sodium iodide in acetone is faster?
A) Cyclohexyl bromide
B) Cyclohexyl p-toluenesulfonate

Answer 23

B) Cyclohexyl p-toluenesulfonate

Question 24

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

Answer 24

D) E2

Question 25

Which one of the following is thermodynamically less stable? A) (E)-Cyclotetradecene B) (Z)-Cyclotetradecene

Answer 25

B) (Z)-Cyclotetradecene

Question 26

``` Which one of the following is soluble in acetone? A) Sodium chloride B) Sodium bromide C) Sodium Iodide D) Sodium p-toluenesulfonate ```

Answer 26

C) Sodium Iodide

Question 27

Which one has the larger heat of hydrogenation? A) (Z)-hex-3-ene B) 2-methylpent-2-ene

Answer 27

A) (Z)-hex-3-ene

Question 28

Which one has the smaller heat of combustion? A) (E)-Cyclooctene B) (Z)-Cyclooctene

Answer 28

B) (Z)-Cyclooctene

Question 29

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

Answer 29

C) Addition of DBr to 1-methylcyclohexene

Question 30

Which one is thermodynamically more stable? A) 2-methylcyclopentyl cation B) 1-methylcyclopentyl cation

Answer 30

B) 1-methylcyclopentyl cation

Question 31

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

Answer 31

C) 1-methylcyclohexene

Question 32

``` 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 ```

Answer 32

C) Tertiary

Question 33

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

Answer 33

B) Cis-1-bromo-2-methylcyclohexane

Question 34

``` 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 ```

Answer 34

B) Markovnikov's Rule

Question 35

Which one has the smaller heat of hydrogenation? A) (E)-pent-2-ene B) Pent-1-ene

Answer 35

A) (E)-pent-2-ene

Question 36

Which one has the larger heat of combustion? A) (E)-Cyclooctene B) (Z)-Cyclooctene

Answer 36

A) (E)-Cyclooctene

Question 37

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

Answer 37

A) Reaction of Cl2 and H2O with 2-methylpent-2-ene

Question 38

Which one has the smaller heat of hydrogenation? A) Cyclononyne B) Cyclodecyne

Answer 38

B) Cyclodecyne

Question 39

``` 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 ```

Answer 39

A) 1-methylcyclohexene

Question 40

``` 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 ```

Answer 40

B) Secondary

Question 41

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

Answer 41

A) Trans-2-methylcyclohexyl p-toluenesulfonate

Question 42

``` 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 ```

Answer 42

C) Zaitsev's Rule