Textbook Question
Predict the major products of the following alkene halogenation reactions. [D is the symbol for deuterium, an isotope of hydrogen.]
(b)
11. Radical Reactions
Anti Markovnikov Addition of Br
1:58 minutesProblem 39e
Textbook Question
What alkyl halide will be obtained in greatest yield? Ignore stereoisomers.
e. 
Verified step by step guidance1
Step 1: Recognize that the reaction involves HBr in the presence of peroxide. This indicates that the reaction will follow the anti-Markovnikov addition mechanism due to the radical pathway initiated by the peroxide.
Step 2: Analyze the structure of the alkene in each case. In the first image, the alkene is part of a cyclohexene ring with a methyl substituent. In the second image, the alkene is part of a cyclohexene ring with a vinyl group and a methyl substituent.
Step 3: Determine the site of radical formation. The anti-Markovnikov addition mechanism involves the bromine radical adding to the less substituted carbon of the double bond, forming the most stable radical intermediate.
Step 4: Predict the major product for each case. In the first image, the bromine will add to the less substituted carbon of the double bond, resulting in the formation of a bromocyclohexane derivative. In the second image, the bromine will add to the less substituted carbon of the double bond in the vinyl group, resulting in a bromocyclohexane derivative with a vinyl substituent.
Step 5: Compare the stability of the radical intermediates and steric effects to determine which alkyl halide will be obtained in the greatest yield. The product with the most stable radical intermediate and least steric hindrance will be favored.
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1mKey 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 fluorine, chlorine, bromine, or iodine). They are classified based on the type of carbon atom to which the halogen is attached: primary, secondary, or tertiary. The structure of the alkyl halide significantly influences its reactivity and the types of reactions it can undergo.
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Nucleophilic Substitution Reactions
Nucleophilic substitution reactions involve the replacement of a leaving group (like a halogen) by a nucleophile. The mechanism can follow either an SN1 or SN2 pathway, depending on the structure of the alkyl halide and the conditions of the reaction. Understanding these mechanisms is crucial for predicting which alkyl halide will be formed in greater yield, as they dictate the rate and outcome of the reaction.
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Reaction Conditions and Yield
The yield of a reaction refers to the amount of product formed compared to the theoretical maximum. Factors such as steric hindrance, solvent effects, and temperature can influence the yield of alkyl halides in nucleophilic substitution reactions. Analyzing these conditions helps determine which alkyl halide will be produced in the greatest yield, as certain structures may favor more efficient pathways.
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