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Chapter 18: Q18-64E (page 594)

How would you synthesize racemic disparlure (Problem 18-63) from compounds having ten or fewer carbons?

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Step by step solution

01

Step-by-step Solution

The Disparlure, is a sex attractant released by the female gypsy moth called Lymantria dispar.

Reaction of disparlure with acid and then with potassium permanganate yields two carboxylic acids gives undecanoic acid and 6-methyl- heptanoic acid.

02

Explanation

The reaction for the synthesis of racemic Displature is shown below.

The compound can be synthesized starting from the 7-methyl octane. It is oxidised using sodium hydrazine, followed by nucleophilic substitution reaction with bromodecane. The triple bond is reduced to cis- alkene using the Lindlars catalyst. The obtained alkene on epoxidation with peroxide gives the racemic mixture of Displature.

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Most popular questions from this chapter

Anethole, , C10H12Oa major constituent of the oil of anise, has the NMR spectrum shown. On oxidation with Na2Cr2O7, anethole yields p-methoxybenzoic acid. What is the structure of anethole? Assign all peaks in the NMR spectrum, and account for the observed splitting patterns

Acid-catalyzed hydrolysis of a 1,2-epoxycyclohexane produces a transdiaxial 1,2-diol. What product would you expect to obtain from acidic hydrolysis of cis-3-tert-butyl-1,2-epoxycyclohexane? (Recall that the bulky tert-butyl group locks the cyclohexane ring into a specific conformation.)

How would you prepare the following ethers? Use whichever method you think is more appropriate, Williamson synthesis or the alkoxymercuration reaction.

  1. Butyl cyclohexyl ether
  2. Benzyl ethyl ether (C6H5CH2OCH2CH3)
  3. sec-Butyl tert-butyl ether
  4. Tetrahydrofuran

Predict the product(s) if the starting materials below underwent a Claisen rearrangement. Draw arrows to illustrate the rearrangement of electrons.

(a)

(b)

(c)

Reaction of cis-2-butene with m-chloroperoxybenzoic acid yields an epoxide different from that obtained by reaction of the trans isomer. Explain.
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