Predict the product of the following reaction:

Propose a mechanism for each reaction, showing explicitly how the observed mixtures of products are formed.

(e) 3-chlorobut-1-ene + AgNO₃, H₂O → but-2-en-1-ol + but-3-en-2-ol

There were actually two possible products in the solvolysis reaction from Figure 21.10. Show both products. Which would you expect to be more stable? Why?

Provide the mechanism and final products for the following reactions.

Rationalize the ranking of increasing reaction rate of the benzylic halides shown.

Predict the product of the following reaction:

Because the S_N1 reaction goes through a flat carbocation, we might expect an optically active starting material to give a completely racemized product. In most cases, however, S_N1 reactions actually give more of the inversion product. In general, as the stability of the carbocation increases, the excess inversion product decreases. Extremely stable carbocations give completely racemic products. Explain these observations.

Allylic halides have the structure

c. Show the products expected from S_N1 solvolysis of these halides in ethanol.

Give the substitution products expected from solvolysis of each compound by heating in ethanol.

(a)

(b)