The benzylic bromide shown undergoes neither S_N1 nor S_N2 substitution reactions. Explain.

To solve this problem, you need to read the description of the Hammett $\sigma$, $\rho$ treatment given in [Chapter 15, Problem 92]. When the rate constants for the hydrolysis of several morpholine enamines of para-substituted propiophenones are determined at pH 4.7, the $\rho$ value is positive; however, when the rates of hydrolysis are determined at pH 10.4, the $\rho$ value is negative.

b. What is the rate-determining step of the hydrolysis reaction when it is carried out in an acidic solution?

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Predict the product for the following substitution reactions. Indicate whether each reaction likely proceeds by an S_N1 or S_N2 mechanism.

(b)

Predict the product for the following substitution reactions. Indicate whether each reaction likely proceeds by an S_N1 or S_N2 mechanism.

(c)

Predict the product(s) of the following reactions.

(h)

Predict the product for the following substitution reactions. Indicate whether each reaction likely proceeds by an S_N1 or S_N2 mechanism.

(a)

Would you expect the following substitution reaction to proceed with inversion or racemization? Why?

Predict the product of the following substitution reactions, making sure to note whether a rearrangement should occur.

(a)

Predict the product of the following substitution reactions, paying close attention to the stereochemical outcome of the reactions.

(f)