Textbook Question
How many alkyl chlorides are obtained from monochlorination of the following alkanes? Disregard stereoisomers.
h.
11. Radical Reactions
Free Radical Halogenation
3:55 minutesProblem 4b
Textbook Question
How many alkyl chlorides are obtained from monochlorination of the following alkanes? Disregard stereoisomers.
b. 
Verified step by step guidance1
Step 1: Identify the structure of the given alkane. The provided structure is 2,3-dimethylpentane, which is a branched alkane.
Step 2: Determine all unique types of hydrogen atoms in the molecule. Hydrogens attached to different carbon environments will lead to different alkyl chlorides upon monochlorination. In this molecule, there are primary, secondary, and tertiary hydrogens.
Step 3: Count the number of unique carbon environments. The molecule has primary carbons (at the ends of the chain), secondary carbons (connected to two other carbons), and tertiary carbons (connected to three other carbons). Each unique carbon environment corresponds to a unique alkyl chloride upon monochlorination.
Step 4: Disregard stereoisomers as instructed. Focus only on the unique carbon environments, not the spatial arrangement of substituents.
Step 5: Sum up the number of unique alkyl chlorides formed. Each unique carbon environment will produce one type of alkyl chloride upon monochlorination.
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Video duration:
3mKey Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Monochlorination
Monochlorination is a specific type of halogenation where one chlorine atom replaces a hydrogen atom in an alkane. This process typically occurs through a free radical mechanism, which involves the generation of chlorine radicals that abstract hydrogen atoms from the alkane, leading to the formation of alkyl chlorides. Understanding this process is crucial for predicting the products formed during the reaction.
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Free Radical Mechanism
The free radical mechanism is a reaction pathway that involves the formation and reaction of free radicals, which are highly reactive species with unpaired electrons. In the context of monochlorination, the mechanism consists of three main steps: initiation, propagation, and termination. Each step plays a vital role in determining the number and types of alkyl chlorides produced from the starting alkane.
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Alkyl Chlorides
Alkyl chlorides are organic compounds derived from alkanes by substituting one or more hydrogen atoms with chlorine atoms. The structure and branching of the original alkane influence the variety of alkyl chlorides formed during monochlorination. Identifying the different alkyl chlorides is essential for understanding the outcomes of the chlorination reaction and for predicting their chemical behavior.
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