Brainscape's Knowledge GenomeTM

Browse over 1 million classes created by top students, professors, publishers, and experts.


See full index

Organic Chemistry > Exam 3 Multiple Choice Questions > Flashcards

Exam 3 Multiple Choice Questions Flashcards

You may prefer our related Brainscape-certified flashcards:
Periodic Table flashcards Chemistry 101 flashcards AP® Chemistry flashcards Organic Chemistry 101 flashcards
1
Q

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

A

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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
2
Q

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

A

B) Cyclohexyl p-toluenesulfonate in DMSO

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
3
Q 
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
A

D) E2

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
4
Q

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

A

A) (E)-Cyclotetradecene

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
5
Q

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

A

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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
6
Q

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

A

B) (R)-2-bromopentane in ethanol

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
7
Q

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

A

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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
8
Q

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

A

A) Cis-1-bromo-3-methylcyclopentane

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
9
Q

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

A

A) (R)-2-chloropentane in DMSO

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
10
Q

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

A

B) Polar Protic

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
11
Q

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

A

B) Pentyl p-toluenesulfonate

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
12
Q

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

A

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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
13
Q

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

A

C) Polar Aprotic

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
14
Q

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

A

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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
15
Q

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

A

A) Dimethyl sulfoxide

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
16
Q

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

A

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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
17
Q

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

A

A) Cyclohexyl bromide in DMSO

18
Q 
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
A

B) SN2

19
Q

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

A

B) (Z)-Cyclononene

20
Q

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

A

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

21
Q

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

A

A) Dimethyl Sulfoxide

22
Q

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

A) Top layer

23
Q

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

A

B) Cyclohexyl p-toluenesulfonate

24
Q 
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
A

D) E2

25
Q

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

A

B) (Z)-Cyclotetradecene

26
Q 
Which one of the following is soluble in acetone?
A) Sodium chloride
B) Sodium bromide
C) Sodium Iodide
D) Sodium p-toluenesulfonate
A

C) Sodium Iodide

27
Q

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

A

A) (Z)-hex-3-ene

28
Q

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

A

B) (Z)-Cyclooctene

29
Q

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

A

C) Addition of DBr to 1-methylcyclohexene

30
Q

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

A

B) 1-methylcyclopentyl cation

31
Q

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

A

C) 1-methylcyclohexene

32
Q 
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
A

C) Tertiary

33
Q

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

A

B) Cis-1-bromo-2-methylcyclohexane

34
Q 
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
A

B) Markovnikov’s Rule

35
Q

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

A

A) (E)-pent-2-ene

36
Q

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

A

A) (E)-Cyclooctene

37
Q

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

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

38
Q

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

A

B) Cyclodecyne

39
Q 
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

A) 1-methylcyclohexene

40
Q 
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
A

B) Secondary

41
Q

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

A) Trans-2-methylcyclohexyl p-toluenesulfonate

42
Q 
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
A

C) Zaitsev’s Rule

Organic Chemistry (2 decks)

Brainscape helps you reach your goals faster, through stronger study habits.
© 2024 Bold Learning Solutions. Terms and Conditions