Consider the bromine addition shown in Figure P15.69 on p. 784. Product A is the

Chapter 15, Problem 15.69

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Consider the bromine addition shown in Figure P15.69 on p. 784. Product A is the predominant product formed at low temperature. If the products are allowed to stand under the reaction conditions or are brought to equilibrium at higher temperature, product B is the only product formed. (a) Which is the kinetic product and which is the thermodynamic product? (b) Give a structural reason that the thermodynamic product is more stable than the kinetic product. (c) Propose a mechanism that explains why the kinetic product is formed more rapidly even though it is less stable. (Hint: The rate-limiting step of bromine addition is formation of the bromonium ion.) (d) Propose a mechanism for the equilibration of the two compounds that does not involve the alkene starting material

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