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Ch.21 - Organic Chemistry
Chapter 21, Problem 48c

List all the possible products for each alkane substitution reaction. (Assume monosubstitution.)
c. CH3CH2CH2CH3 + Cl2

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Identify the type of reaction: This is a halogenation reaction, specifically a free radical substitution reaction where chlorine (Cl2) will replace a hydrogen atom in the alkane.
Determine the structure of the alkane: The given alkane is butane (CH3CH2CH2CH3), which is a straight-chain alkane with four carbon atoms.
Identify the possible sites for substitution: In butane, there are two types of hydrogen atoms - primary (attached to the end carbon atoms) and secondary (attached to the middle carbon atoms).
Consider the possible monosubstitution products: Chlorine can replace a hydrogen atom at either a primary or secondary position, leading to different products.
List the possible products: Substitution at a primary carbon will yield 1-chlorobutane, while substitution at a secondary carbon will yield 2-chlorobutane.

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Key Concepts

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

Alkane Structure

Alkanes are saturated hydrocarbons consisting only of carbon and hydrogen atoms, connected by single bonds. Their general formula is CnH2n+2, where 'n' is the number of carbon atoms. Understanding the structure of alkanes is crucial for predicting the products of substitution reactions, as it determines the sites where reactions can occur.
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Substitution Reactions

Substitution reactions involve the replacement of one atom or group in a molecule with another atom or group. In the case of alkanes, this typically occurs when an alkane reacts with a halogen (like Cl2) under UV light, leading to the formation of haloalkanes. Recognizing the mechanism of these reactions helps in identifying the possible products formed during the process.
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Monosubstitution

Monosubstitution refers to the substitution of a single hydrogen atom in an alkane with a halogen atom. This results in the formation of a haloalkane and a hydrogen halide. In the given reaction, CH3CH2CH2CH3 + Cl2, monosubstitution will yield multiple products depending on which hydrogen is replaced, highlighting the importance of understanding the different positions available for substitution.
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