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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

Aldehydes and ketones undergo acid-catalyzed reaction with alcoholsto yield hemiacetals,compounds that have one alcohol-like oxygenand one ether-like oxygen bonded to the same carbon. Further reactionof a hemiacetal with alcohol then yields an acetal,a compound that hastwo ether-like oxygens bonded to the same carbon.

(a)Show the structures of the hemiacetal and acetal you would obtainby reaction of cyclohexanone with ethanol.

(b)Propose a mechanism for the conversion of a hemiacetal into anacetal.

Give IUPAC names for the following structures:

Meerwein鈥檚 reagent, triethyloxoniumtetrafluoroborate, is a powerful ethylating agent that converts alcohols into ethyl ethers at neutral pH. Show the reaction of Meerwein鈥檚 reagent with cyclohexanol, and account for the fact that trialkyloxonium salts are much more reactive alkylating agents than alkyl iodides.

(CH3CH2)3O+BF4- Meerwein鈥檚 reagent

Predict the major product of each of the following reactions:

Rank the following halides in order of their reactivity in Williamson synthesis:

  1. Bromoethane, 2-bromopropane, bromobenzene
  2. Chloroethane, bromoethane, 1-iodopropene
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