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Chapter 20: Q59 (page 812)

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

Short Answer

Expert verified

a.

b.

c.

Step by step solution

01

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.

02

Epoxide and organolithium reagents

a. The Grignard reagent CH3CH2CH2CH2MgBropens the epoxide ring to give the product Heptan-1-ol.


Opening of epoxide

(b) Nucleophiles C6H5-attack the epoxide from the backside of the ring. This is followed by protonation giving the alkoxide product.

Substitution reaction

(c) The nucleophile CH3CH2CH2- attacks the epoxide. Protonation afterward gives the desired product.

Substitution reaction

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Most popular questions from this chapter

Treatment of isobutene[CH32C=CH2] with(CH3)3CLi forms a carbanion that reacts withCH2=O to form H after water is added to the reaction mixture. H has a molecular ion in its mass spectrum at mz=86, and shows fragments at 71 and 68. H exhibits absorptions in its IR spectrum at 3600–3200 and 1651 cm-1, and has the H1 NMR spectrum given below. What is the structure of H?

Draw the product formed when the α,β-unsaturated ketone A is treated with each reagent.

(a)NaBH4,CH3OH(b)H2,(1equiv),Pd-C(c)H2,(excess),Pd-C(d)[1]CH3Li;[2]H2O(e)[1]CH3CH2MgBr;[2]H2O(f)[1](CH2=CH2)2CuLi;[2]H2O

Draw the products of each reduction reaction.

Draw all stereoisomers formed in each reaction.

Synthesize each compound from the given starting material. You may use any other required inorganic reagents.
See all solutions

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