Textbook Question
How many alkyl chlorides are obtained from monochlorination of the following alkanes? Disregard stereoisomers.
g.
11. Radical Reactions
Free Radical Halogenation
3:24 minutesProblem 4a
Textbook Question
How many alkyl chlorides are obtained from monochlorination of the following alkanes? Disregard stereoisomers.
a. 
Verified step by step guidance1
Step 1: Identify the structure of the given alkane. The image shows a straight-chain alkane with five carbon atoms, which is pentane (C₅H₁₂).
Step 2: Understand monochlorination. Monochlorination involves replacing one hydrogen atom in the alkane with a chlorine atom, resulting in alkyl chlorides.
Step 3: Determine the types of hydrogen atoms in pentane. Pentane has three types of hydrogen atoms based on the carbon they are attached to: primary (on the terminal carbons), secondary (on the carbons adjacent to the terminal carbons), and tertiary (none in this case).
Step 4: Analyze the possible products. Chlorination at different types of hydrogen atoms will yield different alkyl chlorides. For pentane, chlorination at the primary hydrogens (on C1 and C5) and secondary hydrogens (on C2, C3, and C4) will result in distinct products.
Step 5: Count the unique alkyl chlorides. Since stereoisomers are disregarded, focus only on the unique connectivity of the chlorine atom to the carbon chain. Chlorination at C1 and C5 yields the same product, while chlorination at C2, C3, and C4 yields distinct products. Thus, there are three unique alkyl chlorides.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Free Radical Halogenation
Free radical halogenation is a reaction mechanism where alkanes react with halogens (like chlorine) to form alkyl halides. This process involves the generation of free radicals through the homolytic cleavage of the halogen bond, leading to a series of chain reactions. Understanding this mechanism is crucial for predicting the products formed during the monochlorination of alkanes.
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Monochlorination
Monochlorination refers to the substitution of one hydrogen atom in an alkane with a chlorine atom, resulting in the formation of an alkyl chloride. The number of distinct alkyl chlorides produced depends on the structure of the alkane and the positions available for substitution. In this context, it is important to consider the unique carbon environments in the alkane to determine the possible products.
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Alkyl Chlorides
Alkyl chlorides are organic compounds derived from alkanes by replacing one or more hydrogen atoms with chlorine atoms. They can vary in structure based on the carbon chain and branching of the original alkane. Identifying the different alkyl chlorides formed during monochlorination is essential for understanding the reactivity and properties of these compounds in organic chemistry.
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