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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

Reaction of benzyl magnesium chloride with formaldehyde yields alcohols N and P after protonation. Draw a stepwise mechanism that shows how both products are formed.

Propose two different methods to synthesize oct-1-en-3-ol [CH3CH24CHOHCH=CH2] using a Grignard reagent and a carbonyl compound. Oct-1-en-3-ol is commonly called matsutake alcohol because it was first isolated from the Japanese matsutake mushroom.

Draw a stepwise mechanism for the following reaction.

Treatment of compound C (molecular formula C4H8O) with C6H5MgBr, followed by H2O, affords compound D (molecular formula C10H14O). Compound D has a strong peak in its IR spectrum at 3600鈥�3200 cm-1. The H1 NMR spectral data of C and D are given. What are the structures of C and D?Compound C signals at 1.3 (singlet, 6 H) and 2.4 (singlet, 2 H) ppm Compound D signals at 1.2 (singlet, 6 H), 1.6 (singlet, 1 H), 2.7 (singlet, 2 H), and 7.2 (multiplet, 5 H) ppm

Draw the products of the following reactions with organometallic reagents.
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