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E1 and E2 reaction

Total questions: 60

Worksheet time: 36mins

Name
Class
Date
1.
Which of the following statements applies to the E2 mechanism?
a)
It occurs with inversion of stereochemistry
b)
It occurs with racemization
c)
It proceeds through the more stable carbocation intermediate.
d)
The C-H and C-X bonds that break must be anti.
2.
The following energy diagram describes a:
a)
E2 reaction
b)
E1 reaction
c)
Neither
3.
What is the major product of this reaction?
a)
The top one
b)
The bottom one
4.
What is the major product of this reaction?
a)
The first one
b)
The second one
5.
What is the major product of this reaction?
a)
The first one
b)
The second one
6.
What is the major product of this reaction?
a)
The first one
b)
The second one
7.
Which of these conformation can undergo an E2 reaction?
a)
The left one
b)
The right one
c)
Both can undergo an E2 reaction
8.
The mechanism shown is associated with
a)
A E1 reaction
b)
A E2 reaction
c)
Neither
d)
Both
9.
Which statement best describes the reaction?
a)
An E2 with coplanar orientation
b)
An E2 with cis-cis elimination
c)
An E2 that would not occur with this stereochemistry
d)
Neither
10.
A tertiary halide will likely react with a ______ mechanism
a)
SN1 or E2 depending on the solvent characteristics
b)
SN2 always
c)
SN1 or E2 or E1 depending on the base or nucleophile characterisitcs
d)
SN1 or SN2
11.
A primary halide will likely react with a ______ mechanism
a)
SN1 or E2 depending on the solvent characteristics
b)
SN2 most frequently
c)
SN1 or E2 or E1 depending on the base or nucleophile characterisitcs
d)
SN1 or SN2
12.
A secondary halide will likely react with a ______ mechanism
a)
SN1 or E2 depending on the solvent characteristics
b)
SN2 always
c)
SN1 or E2 or E1 depending on the base or nucleophile characterisitcs
d)
SN1 or SN2 or  E2 or E1 depending on the base or nucleophile characterisitcs and the solvent
13.
The reaction mechanism shown below is
a)
SN1 
b)
SN2
c)
E1
d)
E2
14.
Which reaction would most likely occur?
a)
SN2
b)
SN1
c)
E2
d)
E1
15.
Which reaction would most likely occur?
a)
SN2
b)
SN1
c)
E2
d)
E1
16.
The reaction mechanism shown below is
a)
SN1 
b)
SN2
c)
E1
d)
E2
17.
Solvent affects substitution reaction. SN1 reaction is favored by
a)
protic solvent due to its ability to stablize carbocation
b)
aprotic solvent due its ability to stablize carbocation
c)
protic solvent due to hydrogen bonding
d)
aprotic solvent due to lack of hydrogen bonding
18.
Which reaction is most likely going to occur?
a)
SN1
b)
E1
c)
SN2
d)
E2
19.
Which do you expect to be the major product (if any) of this reaction?
a)
The first
b)
The second
c)
Both products would form in equal quantities
20.
Which reaction is most likely going to occur?
a)
SN1
b)
E1
c)
SN2
d)
E2
21.
Which reaction is most likely going to occur?
a)
SN1
b)
E1
c)
SN2
d)
E2
22.

What is the product?

a)

an alkene

b)

an ether

c)

a substitution of OH with CH3

d)

formation of a ketone

23.

What would be the product?

a)

cyclopentene

b)

cyclopentane

c)

cyclopentanol

d)

methoxycyclopentane

24.

Is there no reaction?

a)

This is false. You get phenol and a halogenated benzene as a product.

b)

True, Diaryl ethers like diphenyl ether are inert under ordinary acidic conditions because the generation of an aryl cation is an SN1 process that is energetically unfavorable, and "back-side" attack at the ring carbon bound to oxygen is sterically unfavorable.

c)

True, Hydrogen halides are not strong enough acids to cleave an ether.

d)

This is false. It yields benzene and phenol.

e)

This is false. It yields 2 phenol compounds

25.

The synthesis of epoxides by base treatment of halohydrins is an example of an intramolecular:

a)

dehydration reaction

b)

hydrolysis reaction

c)

Williamson ether synthesis

d)

SN1 reaction

26.

What is the product?

a)

an alkene

b)

an ether

c)

a substitution of OH with CH3

d)

formation of a ketone

27.

Mechanistically, the Williamson ether synthesis outlined is:

a)

an E1 process

b)

an SN1 process

c)

an E2 process

d)

an SN2 process

e)

None of the answers are correct

28.

What would be the product?

a)

cyclopentene

b)

cyclopentane

c)

cyclopentanol

d)

methoxycyclopentane

29.

Is there no reaction?

a)

This is false. You get phenol and a halogenated benzene as a product.

b)

True, Diaryl ethers like diphenyl ether are inert under ordinary acidic conditions because the generation of an aryl cation is an SN1 process that is energetically unfavorable, and "back-side" attack at the ring carbon bound to oxygen is sterically unfavorable.

c)

True, Hydrogen halides are not strong enough acids to cleave an ether.

d)

This is false. It yields benzene and phenol.

e)

This is false. It yields 2 phenol compounds

30.

The synthesis of epoxides by base treatment of halohydrins is an example of an intramolecular:

a)

dehydration reaction

b)

hydrolysis reaction

c)

Williamson ether synthesis

d)

SN1 reaction

31.

What is the missing reagent?

a)

H3O+

b)

HBr, H2O

c)

Br2

32.

Choose the best reagent for carrying out the following reaction

a)

NaOCH3, CH3OH

b)

Hg(O2CCF3)2, CH3OH

c)

LiAlH4 in ether, then H3O+

d)

PCC, CH2Cl2

e)

CH3MgBr in ether, then H3O+

33.

Choose the best reagent for carrying out the following reaction

a)

NaOCH3, CH3OH

b)

Hg(O2CCF3)2, CH3OH

c)

LiAlH4 in ether, then H3O+

d)

PCC, CH2Cl2

e)

CH3MgBr in ether, then H3O+

34.

Choose the best reagent for carrying out the following reaction

a)

NaOCH3, CH3OH

b)

Hg(O2CCF3)2, CH3OH

c)

LiAlH4 in ether, then H3O+

d)

m-ClC6H4CO3H

e)

CH3MgBr in ether, then H3O+

35.

Choose the best reagent for carrying out the following reaction

a)

NaOCH3, CH3OH

b)

Hg(O2CCF3)2, CH3OH

c)

LiAlH4 in ether, then H3O+

d)

m-ClC6H4CO3H

e)

CH3MgBr in ether, then H3O+

36.

Choose the best reagent for carrying out the following reaction

a)

warm H2SO4/H2O

b)

Hg(O2CCF3)2, CH3OH

c)

LiAlH4 in ether, then H3O+

d)

m-ClC6H4CO3H

e)

NaH, then CH3I

37.

______ predicts that the more stable carbocation intermediate is formed in electrophilic additions to alkenes.

a)

Markovnikov's Rule

b)

Cahn-Ingold-Prelog Rules

c)

SN1 rules

d)

Hammond Postulate

38.

Cyclohexanol (—OH bonded to cyclohexane) produces __________ when heated to 70 °C in the presence of a sulfuric acid catalyst.

a)

cyclohexane

b)

cyclohexanone

c)

cyclohexene

d)

dicyclohexyl ether

39.

If the following compound was dissolved in ether and treated with HBr, which of the following describes the major product(s) of the reaction?

a)
b)
c)
d)
40.
The name of this compound is:
a)
ethoxycyclohexane
b)
ethoxybenzene
c)
methoxycyclohexane
d)
methoxybenzene
41.
Rank the following compounds in order of DECREASING boiling point
a)
B > C > A > D
b)
D > A > B > C
c)
A > D > C > B
d)
D > B > C > A
42.
This is not a use of ethers:
a)
anesthetics in hospitals
b)
solvents in industries
c)
to make hand sanitizers
d)
as fuel
43.
Which set of reagents would bring about the following conversion?
a)
NaOEt, EtOH
b)
PAA, H2SO4, EtOH
c)
a. BH3, EtOH b. H2O2, NaOH
d)
a. Hg(OAc)2, EtOH b. NaBH4
44.
Predict the product of the following reaction
a)
A
b)
B
c)
C
d)
D
45.
A tertiary halide will likely react with a ______ mechanism
a)
SN1 or E2 depending on the solvent characteristics
b)
SN2 always
c)
SN1 or E2 or E1 depending on the base or nucleophile characterisitcs
d)
SN1 or SN2
46.
A primary halide will likely react with a ______ mechanism
a)
SN1 or E2 depending on the solvent characteristics
b)
SN2 most frequently
c)
SN1 or E2 or E1 depending on the base or nucleophile characterisitcs
d)
SN1 or SN2
47.
A secondary halide will likely react with a ______ mechanism
a)
SN1 or E2 depending on the solvent characteristics
b)
SN2 always
c)
SN1 or E2 or E1 depending on the base or nucleophile characterisitcs
d)
SN1 or SN2 or  E2 or E1 depending on the base or nucleophile characterisitcs and the solvent
48.
The reaction mechanism shown below is
a)
SN1 
b)
SN2
c)
E1
d)
E2
49.
Which reaction would most likely occur?
a)
SN2
b)
SN1
c)
E2
d)
E1
50.
Which reaction would most likely occur?
a)
SN2
b)
SN1
c)
E2
d)
E1
51.
The reaction mechanism shown below is
a)
SN1 
b)
SN2
c)
E1
d)
E2
52.
Solvent affects substitution reaction. SN1 reaction is favored by
a)
protic solvent due to its ability to stablize carbocation
b)
aprotic solvent due its ability to stablize carbocation
c)
protic solvent due to hydrogen bonding
d)
aprotic solvent due to lack of hydrogen bonding
53.
Which reaction is most likely going to occur?
a)
SN1
b)
E1
c)
SN2
d)
E2
54.
Which do you expect to be the major product (if any) of this reaction?
a)
The first
b)
The second
c)
Both products would form in equal quantities
55.
Which reaction is most likely going to occur?
a)
SN1
b)
E1
c)
SN2
d)
E2
56.
Which reaction is most likely going to occur?
a)
SN1
b)
E1
c)
SN2
d)
E2
57.

The decreasing reactivity of haloalkane towards SN2 reaction

a)

1° > 2°> 3°

b)

3° > 2°> 1°

58.

CH3CH2CH2OH + HBr -----> Product?

What would be the structure of Product?

a)

CH3CH2CH2Cl

b)

CH3CH(Br)CH3

c)

CH3CH2CH2Br

d)

CH3CH2CH2CH2Br

59.

Alcohol X produced cloudy solution immediately with Lucas reagent. Alcohol X is probably a .....

a)

primary alcohol

b)

tertiary alcohol

c)

secondary alcohol

d)

ketone

60.

Factors affecting E1 and E2 reaction-

a)

Type of reactant (1⁰, 2⁰ or 3⁰)

b)

Base used (strong or weak)

c)

Nature of leaving group

d)

All of above

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