Question

What epoxide and organometallic reagents are needed to synthesize each alcohol?

Short answer

a.

b.

c.

Step-by-step solution

Reaction of organometallic reagents with epoxides

When reacted with an epoxide,the organometallic reagent opens the epoxide ring and forms alcohol. The backside attack on epoxide ring followed by protonation gives the alcohol product.

Epoxide and organolithium reagents

a. The Grignard reagent ${\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2{\mathrm{CH}}_2\mathrm{MgBr}$opens the epoxide ring to give the product Heptan-1-ol.

Opening of epoxide

(b) Nucleophiles ${\mathrm{C}}_6{\mathrm{H}}_5^{-}$attack the epoxide from the backside of the ring. This is followed by protonation giving the alkoxide product.

Substitution reaction

(c) The nucleophile ${\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2^{-}$ attacks the epoxide. Protonation afterward gives the desired product.

Substitution reaction