Textbook Question
How many alkyl halides are obtained from monochlorination of the alkanes in Problem 4 if stereoisomers are included?
c.
11. Radical Reactions
Free Radical Halogenation
8:38 minutesProblem 41a
Textbook Question
Propose a mechanism for the following reaction:
Verified step by step guidance1
Step 1: Analyze the reactants and products. The reactants are ethane (CH₃CH₃) and tert-butyl hypochlorite (CH₃C(OCl)(CH₃)₂). The products are ethyl chloride (CH₃CH₂Cl) and tert-butanol (CH₃C(OH)(CH₃)₂). This suggests a radical substitution mechanism.
Step 2: Initiation step. The reaction is initiated by heat (Δ), which causes the homolytic cleavage of the O-Cl bond in tert-butyl hypochlorite, generating a tert-butoxy radical (CH₃C(O•)(CH₃)₂) and a chlorine radical (Cl•).
Step 3: Propagation step 1. The chlorine radical (Cl•) abstracts a hydrogen atom from ethane (CH₃CH₃), forming ethyl radical (CH₃CH₂•) and HCl.
Step 4: Propagation step 2. The ethyl radical (CH₃CH₂•) reacts with another molecule of tert-butyl hypochlorite (CH₃C(OCl)(CH₃)₂), forming ethyl chloride (CH₃CH₂Cl) and regenerating the tert-butoxy radical (CH₃C(O•)(CH₃)₂).
Step 5: Termination step. Two tert-butoxy radicals (CH₃C(O•)(CH₃)₂) combine to form tert-butanol (CH₃C(OH)(CH₃)₂), completing the reaction.
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8mKey Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Reaction Mechanism
A reaction mechanism is a step-by-step description of how a chemical reaction occurs at the molecular level. It outlines the sequence of elementary steps, including bond breaking and formation, and the intermediates formed during the reaction. Understanding the mechanism helps predict the products and the conditions under which the reaction occurs.
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Nucleophiles and Electrophiles
Nucleophiles are species that donate an electron pair to form a chemical bond, while electrophiles are electron-deficient species that accept an electron pair. In organic reactions, identifying the nucleophile and electrophile is crucial for proposing a mechanism, as it determines the direction of electron flow and the formation of products.
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Transition States and Intermediates
Transition states are high-energy states that occur during the transformation from reactants to products, representing the point of maximum energy along the reaction pathway. Intermediates are species that are formed and consumed during the reaction but are not present in the final products. Understanding these concepts is essential for accurately depicting the mechanism and energy changes throughout the reaction.
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