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Chapter 20: Q3P. (page 1038)

In the presence of 18-crown-6, potassium permanganate dissolves inbenzene to give “purple benzene” a useful reagent for oxidizing alkenes in an aprotic environment. Use a drawing of the complex to show why dissolves in benzeneand why the reactivity of the permanganate ion is enhanced.

Short Answer

Expert verified

Crown ethers are macrocyclicpolyethers that form complexes with alkali and alkaline-earth metals. These are known for dissolving ionic substances in organic solvents. 18-crown-6 can particularly solubilize potassium salts in non-polar solvent such as benzene.

Step by step solution

01

Crown ethers

Crown ethers are macrocyclicpolyethers that form complexes with alkali and alkaline-earth metals. These are known for dissolving ionic substances in organic solvents. 18-crown-6 can particularly solubilize potassium salts in non-polar solvent such as benzene.

02

18-crown-6

18-crown-6 has the tendency to solubilize metal salts, especially "potassium salts." It happens in both dipolar and nonpolar aprotic solvents.

18-crown-6 makes potassium permanganate more soluble in benzene and it holds the potassium ion tightly which makes permanganate more available for the reaction.

This organic compound is not complexed with other solvent molecules.

Product formed by the reaction of 18-crown-6 with benzene

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Most popular questions from this chapter

There are three dioxane isomers: 1,2-dioxane, 1,3- dioxane, and 1,4-dioxane. One of these acts like an ether and is an excellent solven for Grignard reactions. Another one is potentially explosive when heated. The third one quickly hydrolyzes in dilute acid. Show which isomer acts like a simple ether, and then explain why one of them is potentially explosive. Propose a mechanism for the acid hydrolysis of the third isomer.

Question: A carboxylic acid has two oxygen atoms, each with two nonbonding pairs of electrons.

  1. Draw the resonance forms of a carboxylic acid that is protonated on the hydroxy oxygen atom.
  2. Compare the resonance forms with those given previously for an acid protonated on the carbonyl oxygen atom.
  3. Explain why the carbonyl oxygen atom of a carboxylic acid is more basic than the hydroxy oxygen.

Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.

(a) isopentyl alcohol isopentyl acetate (banana oil)

(b) 3-ethylpentanoic acid3-ethylpentanenitrile

(c) isobutylamineN-isobutylformamide

(d) ethyl acetate3-methylpentan-3-ol

(e) cyclohexylamineN-cyclohexylacetamide

(f) bromocyclohexanedicyclohexylmethano

(g)

(h)

Phenols (pKa≈ 10) are more acidic than other alcohols, so they are easily deprotonated by sodium hydroxide or potassium hydroxide. The anions of phenols (phenoxide ions) can be used in the Williamson ether synthesis, especially with very reactive alkylating reagents such as dimethyl sulfate. Using phenol, dimethyl sulfate, and other necessary reagents, show how you would synthesize methyl phenyl ether.

Show how you would synthesize 2-phenylhex-3-yn-2-ol, starting with acetophenone (PhCOCH3 ) and any other reagents you need. (“2-ol” means there is an OH group on C2.)
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