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Ch.21 - Organic Chemistry
All textbooksTro 4th EditionCh.21 - Organic ChemistryProblem 47c
Chapter 21, Problem 47c

List all the possible products for each alkane substitution reac- tion. (Assume monosubstitution.)
c. CH2Cl2 + Br2 →

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Identify the type of reaction: This is a halogenation reaction, specifically a substitution reaction where a hydrogen atom in the alkane is replaced by a halogen atom.
Determine the possible sites for substitution: In the given compound, dichloromethane (CH2Cl2), there are two hydrogen atoms that can be substituted by bromine atoms.
Consider the substitution of one hydrogen atom: Replace one hydrogen atom in CH2Cl2 with a bromine atom to form bromochloromethane (CHBrCl2).
Consider the substitution of the other hydrogen atom: Replace the other hydrogen atom in CH2Cl2 with a bromine atom to form another possible product, dibromochloromethane (CHBr2Cl).
List the possible monosubstitution products: The possible products are bromochloromethane (CHBrCl2) and dibromochloromethane (CHBr2Cl).

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Alkane Substitution Reactions

Alkane substitution reactions involve the replacement of one hydrogen atom in an alkane with another atom or group, typically through a free radical mechanism. In these reactions, alkanes react with halogens (like Br2) under specific conditions, leading to the formation of haloalkanes. Understanding the mechanism of these reactions is crucial for predicting the products formed.
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Free Radical Mechanism

The free radical mechanism is a process that occurs in substitution reactions where free radicals (highly reactive species with unpaired electrons) are generated. This mechanism typically involves three steps: initiation, propagation, and termination. In the presence of light or heat, Br2 can dissociate into two bromine radicals, which then react with the alkane to form products.
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Product Distribution

In alkane substitution reactions, the distribution of products depends on the structure of the alkane and the conditions of the reaction. For example, when CH2Cl2 reacts with Br2, the substitution can occur at different positions, leading to various haloalkane products. Identifying all possible products requires considering the different sites of substitution and the stability of the resulting radicals.
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Related Practice
Textbook Question

Complete and balance each hydrocarbon combustion reaction. a. CH3CH2CH2CH3 + O2 → b.CH2=CHCH3 + O2 → c. CH≡CCH2CH3 + O2 →

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Textbook Question

List all the possible products for each alkane substitution reaction. (Assume monosubstitution.) a. CH3CH3 + Br2 →

Textbook Question

List all the possible products for each alkane substitution reaction. (Assume monosubstitution.) b. CH3CH2CH3 + Cl2 → d.

Textbook Question

List all the possible products for each alkane substitution reaction. (Assume monosubstitution.) a.CH4 +Cl2 → b. CH3CH2Br + Br2 → d. CH3CHBr2 + Br2 →

Textbook Question

List all the possible products for each alkane substitution reaction. (Assume monosubstitution.)

c. CH3CH2CH2CH3 + Cl2 →