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Chapter 22: Problem 112

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. a. 2,2 -dimethylpropane \(+\mathrm{Cl}_{2} \stackrel{h v}{\longrightarrow}\) b. 1,3 -dimethylcyclobutane \(+\mathrm{Cl}_{2} \stackrel{h v}{\longrightarrow}\) c. 2,3 -dimethylbutane \(+\mathrm{Cl}_{2} \stackrel{h v}{\longrightarrow}\)

Short Answer

Expert verified
a. Monochlorinated 2,2-dimethylpropane products are \(CCl(CH_3)_3\) and \(C(CH_3)_3(CH_2Cl)\). b. Monochlorinated 1,3-dimethylcyclobutane products are \(C_4H_6(CH_3)_2Cl\) with Cl in either primary or secondary carbon positions. c. Monochlorinated 2,3-dimethylbutane products are \(CH_3CH(CH_3)CH(CH_3)CH_2Cl\) and \(CH_3CH(CH_3)CH(Cl)CH_3\).

Step by step solution

01

Identify the positions for the substitution

Determine the possible positions for the chlorine-substitution within the molecule. 2,2-dimethylpropane has the structure: C(CH₃)₄ There are only two types of hydrogens present in the molecule: - The central carbon atom has 1 hydrogen on it. - The 4 methyl (CH₃) groups have 3 hydrogens each.
02

Draw the possible products

Now draw the possible monochlorination products of 2,2-dimethylpropane by substituting one hydrogen atom at these positions with chlorine. We have two possibilities: 1. Chlorination at the central carbon atom. 2. Chlorination at any of the methyl groups. These two possibilities result in two unique products. Both products are chiral since the central carbon in the products is tetrahedral and has four different substituents. b. 1,3 -dimethylcyclobutane + Cl₂ → Monochlorinated 1,3-dimethylcyclobutane
03

Identify the positions for the substitution

Determine the possible positions for the chlorine-substitution within the molecule. 1,3-dimethylcyclobutane has the structure: C₄H₆(CH₃)₂ The hydrogens in this molecule can be categorized as follows: - 4 primary hydrogens attached to the carbons without methyl groups. - 6 secondary hydrogens (3 on each carbon with a methyl group).
04

Draw the possible products

Draw the possible monochlorination products of 1,3-dimethylcyclobutane by substituting one hydrogen atom at these positions with chlorine. We have two possibilities: 1. Chlorination at the carbon atoms without methyl groups (primary). 2. Chlorination at the carbon atoms with methyl groups (secondary). These two possibilities result in two unique products. c. 2,3 -dimethylbutane + Cl₂ → Monochlorinated 2,3-dimethylbutane
05

Identify the positions for the substitution

Determine the possible positions for the chlorine-substitution within the molecule. 2,3-dimethylbutane has the structure: CH₃CH(CH₃)CH(CH₃)CH₃ The hydrogens in this molecule can be classified as follows: - 6 primary hydrogens on the terminal carbons. - 2 secondary hydrogens on the carbons-bound to the methyl groups.
06

Draw the possible products

Draw the possible monochlorination products of 2,3-dimethylbutane by substituting one hydrogen atom at these positions with chlorine. We have two possibilities here: 1. Chlorination at the terminal carbons (primary). 2. Chlorination at the carbons-bound to the methyl groups (secondary). These two possibilities result in two unique products.

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Most popular questions from this chapter

A confused student was doing an isomer problem and listed the following six names as different structural isomers of \(\mathrm{C}_{7} \mathrm{H}_{16}\) a. 1 -sec-butylpropane b. 4 -methylhexane c. 2 -ethylpentane d. 1 -ethyl-1-methylbutane e. 3 -methylhexane f. 4 -ethylpentane How many different structural isomers are actually present in these six names?

Draw the following. a. cis \(-2\) -hexene b. trans-2-butene c. cis-2,3-dichloro-2-pentene

Name all the aldehydes and ketones that have the formula \(\mathrm{C}_{5} \mathrm{H}_{10} \mathrm{O}\).

Draw all structural and geometrical (cis-trans) isomers of \(\mathrm{C}_{4} \mathrm{H}_{7} \mathrm{~F}\). Ignore any cyclic isomers.

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