What stereoisomers are obtained from the reaction of the alkenes in [PROBLEM 10-32] with a peroxyacid ­followed by reaction with hydroxide ion?

a. trans-2-butene

b. cis-2-butene

What stereoisomers are obtained from the reaction of the alkenes in [PROBLEM 10-32] with a peroxyacid ­followed by reaction with hydroxide ion?

c. cis-2-pentene

d. trans-2-pentene

Draw the mechanism for formation of the two addition products.

Draw all possible resonance contributors for the two carbocations in the preceding reaction. Use the resonance contributors to explain why 1-naphthol is the major product of the reaction.

The existence of the NIH shift was established by determining the major product obtained from rearrangement of the following arene oxide, in which a hydrogen has been replaced by a deuterium.

a. What would be the major product if the NIH shift occurs? (Hint: A C—H bond is easier to break than a C—D bond.)

The existence of the NIH shift was established by determining the major product obtained from rearrangement of the following arene oxide, in which a hydrogen has been replaced by a deuterium.

b. What would be the major product if the carbocation forms phenol by losing H⁺ or D⁺, rather than by going through the NIH shift?

How do the major products obtained from rearrangement of the following arene oxides differ?

Explain why the two arene oxides in [PROBLEM 10-38] open in opposite directions.

Three arene oxides can be obtained from phenanthrene.

a. Draw the structures of the three phenanthrene oxides.

Three arene oxides can be obtained from phenanthrene.

c. If a phenanthrene oxide can lead to the formation of more than one phenol, which phenol will be obtained in greater yield?

Three arene oxides can be obtained from phenanthrene.

d. Which of the three phenanthrene oxides is most likely to be carcinogenic?

Explain why the half-life (the time it takes for one-half of the compound to be metabolized) of Xylocaine is longer than that of Novocaine.

If a quaternary ammonium ion can undergo an elimination reaction with a strong base, why can’t a protonated tertiary amine undergo the same reaction?

What are the major products of the following reaction?

What are the minor products of the preceding Hofmann elimination reaction?

What is the major product of each of the following reactions?

b .

Describe a synthesis for each of the following compounds, using the given starting material and any necessary reagents:

b.

Using an alkyl halide and a thiol as starting materials, how would you prepare the following thioethers?

a.

Using an alkyl halide and a thiol as starting materials, how would you prepare the following thioethers?

b.

Using an alkyl halide and a thiol as starting materials, how would you prepare the following thioethers?

c.

d.

The following three nitrogen mustards were studied for possible clinical use. One is now used clinically, one was found to be too unreactive, and one was found to be too insoluble in water to be injected intravenously. Which is which? (Hint: Draw resonance contributors.)

Why is melphalan a good cancer drug?

What is the product of each of the following reactions?

a.

What is the product of each of the following reactions?

c.

d.

What is the product of each of the following reactions?

g.

Indicate which alcohol in each pair undergoes an elimination reaction more rapidly when heated with H₂SO₄.

a.

b.

Indicate which alcohol in each pair undergoes an elimination reaction more rapidly when heated with H₂SO₄.

c.

Indicate which alcohol in each pair undergoes an elimination reaction more rapidly when heated with H₂SO₄.

d.

Indicate which alcohol in each pair undergoes an elimination reaction more rapidly when heated with H₂SO₄.

e.

Identify A–E.