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?

What products are obtained from the reaction of cyclohexene oxide with

b. methylamine?

b. A small amount of a product containing a six-membered ring is also formed. Draw the structure of that product.

c. Why is so little six-membered ring product formed?

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

Cellosolve® is the trade name for 2-ethoxyethanol, a common industrial solvent. This compound is produced in chemical plants that use ethylene as their only organic feedstock. Show how you would accomplish this industrial process.

Show the rest of the mechanism for formation of the cyclized intermediate in Figure 14-6.

Predict the products of the following reactions.

(g) trans-2,3-epoxyoctane + H⁺, H₂O

(h) propylene oxide + methylamine (CH₃NH₂)

Propylene oxide is a chiral molecule. Hydrolysis of propylene oxide gives propylene glycol, another chiral molecule.

(a) Draw the enantiomers of propylene oxide.

(b) Propose a mechanism for the acid-catalyzed hydrolysis of pure (R)-propylene oxide.