Textbook Question
How many alkyl halides are obtained from monochlorination of the alkanes in Problem 4 if stereoisomers are included?
h.
11. Radical Reactions
Free Radical Halogenation
2:02 minutesProblem 6b
Textbook Question
How many alkyl halides are obtained from monochlorination of the alkanes in Problem 4 if stereoisomers are included?
b. 
Verified step by step guidance1
Step 1: Identify the structure of the alkane provided in the image. The structure is 2,3-dimethylbutane, which is a branched alkane.
Step 2: Determine the possible sites for monochlorination. Monochlorination involves replacing one hydrogen atom with a chlorine atom. Analyze the molecule to find all unique hydrogen environments (primary, secondary, tertiary hydrogens).
Step 3: Consider the symmetry of the molecule. Due to the symmetry in 2,3-dimethylbutane, some hydrogen environments will be equivalent, reducing the number of unique products.
Step 4: Account for stereoisomers. If monochlorination occurs at a chiral center, stereoisomers (R and S configurations) must be considered as separate products.
Step 5: Count all unique alkyl halides, including stereoisomers, formed from monochlorination at each unique hydrogen environment. This will give the total number of alkyl halides obtained.
Verified video answer for a similar problem:This video solution was recommended by our tutors as helpful for the problem above
Video duration:
2mKey Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Alkyl Halides
Alkyl halides are organic compounds derived from alkanes by replacing one or more hydrogen atoms with halogen atoms (such as chlorine, bromine, or iodine). They can be classified as primary, secondary, or tertiary based on the carbon atom to which the halogen is attached. Understanding the structure and classification of alkyl halides is crucial for predicting their reactivity and the products formed during reactions like halogenation.
Recommended video:
Guided course
01:52
How to name alkyl halides
Free Radical Halogenation
Free radical halogenation is a reaction mechanism where alkanes react with halogens (like Cl2 or Br2) in the presence of heat or light to form alkyl halides. This process involves the formation of free radicals, which are highly reactive species with unpaired electrons. The reaction proceeds through initiation, propagation, and termination steps, and understanding this mechanism is essential for predicting the products and their stereochemistry.
Recommended video:
Guided course
12:11Radical Chain Reaction Mechanism.
Stereoisomerism
Stereoisomerism occurs when compounds have the same molecular formula and connectivity but differ in the spatial arrangement of their atoms. In the context of alkyl halides, the presence of chiral centers can lead to the formation of enantiomers or diastereomers. Recognizing the potential for stereoisomers is important when determining the total number of distinct products formed from reactions like monochlorination, as each stereoisomer represents a unique compound.
Recommended video:
Guided course
01:58Determining when molecules are stereoisomers.
Related Videos
Related Practice