Questions on Radicals

1.

Which of the following are the products of a homolytic cleavage of a C-C bond of ethane? A)

2

B)

CH3

CH3

C)

H

D)

2

+

+

CH3
CH2H3

CH3

Ans: A

Chapter 11
Topic: Radicals
Section: 11.1
Difficulty Level: Easy
2.

Which of the following is the most stable radical?

A)

B)

C)

D)

E)

Ans: B

Chapter 11
Topic: Radicals
Section: 11.1
Difficulty Level: Easy
3.

In the molecule shown below, determine which of the labeled bonds is expected to have the lowest bond dissociation energy.
H

A H

H

H

H
C

C
C

H
H

C
H

B

Ans: C
Chapter 11
Topic: Radicals
Section: 11.1
Difficulty Level: Easy

H

C

C
C
H
CH3

C

H

D

E

4.

Use correct arrow formalism to show a homolytic bond cleavage of ethane to produce two methyl radicals.
Ans: H3C

CH3

CH3

+ CH3

Chapter 11
Topic: Radicals
Section: 11.1
Difficulty Level: Medium
5.

Rank the following radicals in order of decreasing stability (most stable to least stable). I
A)
B)
C)
D)
E)

II

III

IV

IV > I > II > III
III > I > II > IV
III > II > I > IV
III > IV > II > I
II > III > I > IV

Ans: C

Chapter 11
Topic: Radicals
Section: 11.1
Difficulty Level: Difficult
6.

Rank the following radicals in order of decreasing stability (most stable to least stable). Cl

Cl

Cl

I
A)
B)
C)
D)
E)

Cl

II

III

IV

IV > I > II > III
III > I > II > IV
III > II > I > IV
III > IV > II > I
II > I > III > IV

Ans: E

Chapter 11
Topic: Radicals
Section: 11.1
Difficulty Level: Medium
7.

Using correct arrow formalism, draw all the resonance structures for the radical shown below.

Ans:
Chapter 11
Topic: Radicals
Section: 11.1
Difficulty Level: Medium
8.

Use correct arrow formalism to draw all the resonance structure for the radical shown below.

Ans:
Chapter 11
Topic: Radicals
Section: 11.1
Difficulty Level: Medium
9.