Exam 3 Multiple Choice Questions Flashcards Preview

Organic Chemistry > Exam 3 Multiple Choice Questions > Flashcards

Flashcards in Exam 3 Multiple Choice Questions Deck (42)
Loading flashcards...
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

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

2

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

B) Cyclohexyl p-toluenesulfonate in DMSO

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

D) E2

4

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

A) (E)-Cyclotetradecene

5

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

6

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

B) (R)-2-bromopentane in ethanol

7

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

8

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

A) Cis-1-bromo-3-methylcyclopentane

9

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

A) (R)-2-chloropentane in DMSO

10

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

B) Polar Protic

11

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

B) Pentyl p-toluenesulfonate

12

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

13

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

C) Polar Aprotic

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

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

15

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

A) Dimethyl sulfoxide

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

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

17

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

A) Cyclohexyl bromide in DMSO

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

B) SN2

19

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

B) (Z)-Cyclononene

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

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

21

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

A) Dimethyl Sulfoxide

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

A) Top layer

23

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

B) Cyclohexyl p-toluenesulfonate

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

D) E2

25

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

B) (Z)-Cyclotetradecene

26

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

27

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

A) (Z)-hex-3-ene

28

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

B) (Z)-Cyclooctene

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

C) Addition of DBr to 1-methylcyclohexene

30

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

B) 1-methylcyclopentyl cation

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

C) 1-methylcyclohexene

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

C) Tertiary

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

B) Cis-1-bromo-2-methylcyclohexane

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

B) Markovnikov's Rule

35

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

A) (E)-pent-2-ene

36

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

A) (E)-Cyclooctene

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

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

38

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

B) Cyclodecyne

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

A) 1-methylcyclohexene

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

B) Secondary

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

A) Trans-2-methylcyclohexyl p-toluenesulfonate

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

C) Zaitsev's Rule