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Chapter 22: Problem 122

In the presence of light, chlorine can substitute for one (or more) of the hydrogens in an alkane. For the following reactions, draw the possible monochlorination products. $$ 2,2 \text { -dimethylpropane }+\mathrm{Cl}_{2} \longrightarrow $$ $$ 1,3 \text { -dimethylcyclobutane }+\mathrm{Cl}_{2} \stackrel{\mathrm{hn}}{\longrightarrow} $$ $$ 2,3 \text { -dimethylbutane }+\mathrm{Cl}_{2} \stackrel{\mathrm{w}}{\longrightarrow} $$

Short Answer

Expert verified
For the given alkanes, the possible monochlorination products are: 1. 2,2-dimethylpropane: 1-chloro-2,2-dimethylpropane 2. 1,3-dimethylcyclobutane: 1-chloro-1,3-dimethylcyclobutane, 3-chloro-1,3-dimethylcyclobutane, and (1,3-dimethylcyclobutane-2-yl) chloride 3. 2,3-dimethylbutane: 1-chloro-2,3-dimethylbutane, 2-chloro-2,3-dimethylbutane, 3-chloro-2,3-dimethylbutane, and 4-chloro-2,3-dimethylbutane.

Step by step solution

01

1. 2,2-dimethylpropane + Cl₂ → ?

Identify the hydrogen positions in 2,2-dimethylpropane that can be substituted. There are 12 hydrogens, all in equivalent positions. Substituting one hydrogen with chlorine will result in only one possible product, 1-chloro-2,2-dimethylpropane. Product: $$ 1-\text{chloro-2,2-dimethylpropane} $$
02

2. 1,3-dimethylcyclobutane + Cl₂ → ?

Identify the hydrogen positions in 1,3-dimethylcyclobutane that can be substituted. There are three different sets of hydrogens, making three possible products: 1-chloro-1,3-dimethylcyclobutane, 3-chloro-1,3-dimethylcyclobutane, and 1,3-dimethylcyclobutane-2-yl chloride. Products: $$ \text{1-chloro-1,3-dimethylcyclobutane} $$ $$ \text{3-chloro-1,3-dimethylcyclobutane} $$ $$ (\text{1,3-dimethylcyclobutane-2-yl})\;\text{chloride} $$
03

3. 2,3-dimethylbutane + Cl₂ → ?

Identify the hydrogen positions in 2,3-dimethylbutane that can be substituted. There are four different sets of hydrogens, making four possible products: 1-chloro-2,3-dimethylbutane, 2-chloro-2,3-dimethylbutane, 3-chloro-2,3-dimethylbutane, and 4-chloro-2,3-dimethylbutane. Products: $$ \text{1-chloro-2,3-dimethylbutane} $$ $$ \text{2-chloro-2,3-dimethylbutane} $$ $$ \text{3-chloro-2,3-dimethylbutane} $$ $$ \text{4-chloro-2,3-dimethylbutane} $$

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