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When (1-bromoethyl)cyclohexane is heated in methanol for an extended period of time
Chapter 7, Problem PROBLEM 7-22(choose chapter or problem)
When (1-bromoethyl)cyclohexane is heated in methanol for an extended period of time, five products result: two ethers and three alkenes. Predict the products of this reaction, and propose mechanisms for their formation. Predict which of the three alkenes is the major elimination product.
Questions & Answers
QUESTION:
When (1-bromoethyl)cyclohexane is heated in methanol for an extended period of time, five products result: two ethers and three alkenes. Predict the products of this reaction, and propose mechanisms for their formation. Predict which of the three alkenes is the major elimination product.
ANSWER:Step 1 of 5
Unimolecular nucleophilic substitution reaction
Nucleophilic substitution reactions in two steps are called unimolecular substitutions or reactions. In the mechanism, the substrate forms a carbocation in the first step, which reacts with a nucleophile in the second step to form the substituted product. The carbocation formation is the rate-determining step of the reaction, and therefore reactions are first-order reactions.
Unimolecular elimination reactions
Elimination reactions that include two steps, namely, an ionization step and deprotonation step, are called unimolecular elimination. In this mechanism, the leaving group is removed first, forming a carbocation from which a beta proton is removed to form an alkene.