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Exam 15: Radical Reactions

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Question 21

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Determine the product(s) of the following reaction.

A) Only I
B) Only II
C) Only III
D) Only I and II

E) A) and C)
F) B) and C)

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Question 22

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How many monochlorination products can be formed (constitutional isomers only) from the reaction of (CH₃) ₂CHCH₂CH₃ with Cl₂ and h?

A) 2
B) 3
C) 4
D) 5

E) A) and B)
F) A) and C)

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Question 23

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Determine the monochlorination product(s)

Which of the following statements is (are) true about free radical halogenation of alkanes?

A possible reaction of ethane with chlorine is shown below. $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 3 } + \mathrm { Cl } _ { 2 } \longrightarrow \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { Cl } + \mathrm { HCl }$ This reaction could conceivably occur by the following chain mechanisms [1], [2], and [3]. The chain propagating step(s) is (are) _______. $[ 1 ] \quad \mathrm { Cl } _ { 2 } \longrightarrow 2 \mathrm { Cl } \cdot$ [2] $\mathrm { Cl } \cdot + \mathrm { CH } _ { 3 } \mathrm { CH } _ { 3 } \stackrel { \text { slow } } { \longrightarrow } \mathrm { HCl } + \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 }^ \cdot$ [3] $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } ^\cdot + \mathrm { Cl } _ { 2 } \stackrel { \text { fast } } { \longrightarrow } \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { Cl } + \mathrm { Cl }\cdot$ .

What is the product of the following reaction?

Which of the following statements about the stereochemistry of halogenation reactions is true?

Which of the following statements about the propagation steps in the chlorination of ethane is true?

Which of the following statements about chlorination and bromination is true?

Which of the following is a radical scavenger?

A possible reaction of ethane with chlorine is shown below. $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 3 } + \mathrm { Cl } _ { 2 } \longrightarrow \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { Cl } + \mathrm { HCl }$ This reaction could conceivably occur by the following chain mechanisms [1], [2], and [3]. Determine ?H for step [2]. [1] $\quad \mathrm { Cl } _ { 2 } \longrightarrow 2 \mathrm { Cl } \cdot$ [2] $\mathrm { Cl } ^ { \cdot } + \mathrm { CH } _ { 3 } \mathrm { CH } _ { 3 } \stackrel { \text { slow } } { \longrightarrow } \mathrm { HCl } + \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } ^ \cdot$ $[ 3 ] \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } ^ \cdot + \mathrm { Cl } _ { 2 } \stackrel { \text { fast } } { \longrightarrow } \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { Cl } + \mathrm { Cl } ^\cdot$ Bond dissociation energies (kcal/mol) : $\begin{array} { | l l | } \hline \text { Bond A-B } & \Delta \mathrm { H } \\\hline \mathrm { Cl } - \mathrm { Cl } & 58 \\\mathrm { CH } _ { 3 } - \mathrm { H } & 104 \\\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } - \mathrm { H } & 98 \\\mathrm { CH } _ { 3 } \mathrm { CH } _ { 3 } & 88 \\\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } - \mathrm { Cl } & 81 \\\mathrm { H } - \mathrm { Cl } & 103 \\\hline\end{array}$

Which of the following statements about radicals and radical reactions is not true?

A possible reaction of ethane with chlorine is shown below. $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 3 } + \mathrm { Cl } _ { 2 } \longrightarrow \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { Cl } + \mathrm { HCl }$ This reaction could conceivably occur by the following chain mechanisms [1], [2], and [3]. Determine ?H for step [1]. [1] $\mathrm { Cl } _ { 2 } \longrightarrow 2 \mathrm { Cl } \cdot$ [2] $\mathrm { Cl } \cdot + \mathrm { CH } _ { 3 } \mathrm { CH } _ { 3 } \stackrel { \text { slow } } { \longrightarrow } \mathrm { HCl } + \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } ^ \cdot$ [3] $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } ^ \cdot+ \mathrm { Cl } _ { 2 } \stackrel { \text { fast } } { \longrightarrow } \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { Cl } + \mathrm { Cl }\cdot$ . Bond dissociation energies (kcal/mol) : $\begin{array} { | l | l | } \hline \text { Bond A-B } & \Delta \mathrm { H } \\\hline \mathrm { Cl } - \mathrm { Cl } & 58 \\\mathrm { CH } _ { 3 } - \mathrm { H } & 104 \\\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } - \mathrm { H } & 98 \\\mathrm { CH } _ { 3 } - \mathrm { CH } _ { 3 } & 88 \\\mathrm { CH } _ { 3 } - \mathrm { Cl } & 84 \\\mathrm { H } - \mathrm { Cl } & 103 \\\hline\end{array}$

Which of the labeled hydrogens is most easily abstracted in a free radical bromination reaction?

Identify the monomer used to make the following polymer.

Rank the following radicals in order of decreasing stability, putting the most stable first. $\mathrm { CH } _ { 3 } \dot { \mathrm { C } } \mathrm { H } _ { 2 }\quad$ $\mathrm { H } _ { 2 } \mathrm { C } = \mathrm { C } \dot { \mathrm { C } } \mathrm { H } _ { 2 }\quad$ $\mathrm { CH } _ { 3 } \dot { \mathrm { C } } \mathrm { HCH } _ { 3 }\quad$ $\left( \mathrm { CH } _ { 3 } \right) _ { 3 } \dot { \mathrm { C } }$ I $\quad\quad\quad\quad\quad\quad\quad$ II $\quad\quad\quad\quad\quad\quad\quad$ III $\quad\quad\quad\quad\quad$ IV

Which of the following compounds contain primary (1°) radical carbons?

Which of the following statements about radicals is true?

Which of the following statements about carbon radicals is not true?

How many monochlorination products (constitutional isomers and stereoisomers) are formed from the reaction of pentane with Cl₂ and h?