Organic Chemistry I

Maryam Fardpour

In each case provide an explanation for the

failure of the reaction to take place as

indicated.

Your task is to prepare isopropyl methyl ether by

one of the following reactions. Which reaction

would give the better yield? Explain your answer.

Reaction (2) would give the better yield

because the desired reaction is an SN2

reaction, and the substrate is a methyl halide.

Use of reaction (1) would, because the

substrate is a secondary halide, result in

considerable elimination by an E2 pathway.

Starting with an appropriate alkyl halide and using any other

needed reagents, outline syntheses of each of the following.

When alternative possibilities exist for a synthesis, you should

be careful to choose the one that gives the better yield.

Which product (or products) would you expect to obtain from each of the

following reactions? In each part give the mechanism (SN1, SN2, E1, or

E2) by which each product is formed and predict the relative amount of

each product (i.e., would the product be the only product, the major

product, a minor product, etc.?).