Chapter 8: 8-99P (page 380)
Draw the major products obtained from the reaction of one equivalent of HBr with the following compounds. For each reaction, indicate the kinetic product and the thermodynamic product.

Short Answer
a)

b)

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Chapter 8: 8-99P (page 380)
Draw the major products obtained from the reaction of one equivalent of HBr with the following compounds. For each reaction, indicate the kinetic product and the thermodynamic product.

a)

b)

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What is the major product of each of the following reactions, assuming that one equivalent of each reagent is used in each reaction?

a. When HBr adds to a conjugated diene, what is the rate-determining step?
b. When HBr adds to a conjugated diene, what is the product-determining step?
a. Predict the relative pKa values of cyclopentadiene and cycloheptatriene.
b. Predict the relative pKa values of cyclopropene and cyclopropane.
a. Why does deuterium add to C-1 rather than to C-4 in the preceding reaction?
b. Why was DCl rather than HCl used in the reaction?
In 1935, J. Bredt, a German chemist, proposed that a bicycloalkene could not have a double bond at a bridgehead carbon unless one of the rings contains at least eight carbons. This is known as Bredt’s rule. Explain why there cannot be a double bond at this position.

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