The following reaction resembles the acid-catalyzed cyclization of squalene oxide. Propose a mechanism for this reaction.

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.

Predict the major products of the following reactions, including stereochemistry.

f. trans-pent-2-ene + peroxyacetic acid in water

a. Propose a mechanism for the conversion of cis-hex-3-ene to the epoxide (3,4-­epoxyhexane) and the ring-opening reaction to give the glycol, hexane-3,4-diol. In your mechanism, pay particular attention to the stereochemistry of the intermediates and products.

b. Repeat part (a) for trans-hex-3-ene. Compare the products obtained from cis- and trans-hex-3-ene. Is this reaction sequence stereospecific?

Predict the major product when each reagent reacts with ethylene oxide.

(d) PhNH₂ (aniline)

(e) KCN (potassium cyanide)

(f) NaN₃ (sodium azide)

Predict the major products of the following reactions, including stereochemistry where appropriate.

(c) (2S,3R)-2-ethyl-2,3-dimethyloxirane + CH₃O^– / CH₃OH

(d) (2S,3R)-2-ethyl-2,3-dimethyloxirane + H⁺ / CH₃OH

Under the right conditions, the following acid-catalyzed double cyclization proceeds in remarkably good yields. Propose a mechanism. Does this reaction resemble a biological process you have seen? 

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (vii) 1. mCPBA 2. H₂SO₄, H₂O

(d)

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (vii) 1. mCPBA 2. H₂SO₄, H₂O

(k)