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Chapter 20: Q61P (page 1038)

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.

Short Answer

Expert verified

behaves like a simple ether. easily hydrolyzes in aqueous acid. is potentially explosive.

Mechanism for acidic hydrolysis of 1, 3 dioxanes

Step by step solution

01

Predicting the behavior of given isomers

1, 4 dioxanes behaves like a simple ether and it is a good solvent for Grignard reaction.

1, 3 dioxanes easily hydrolyzes in aqueous acid.

1, 2 dioxanes is potentially explosive. The bonds between oxygen atoms in a peroxide stores an enormous amount of energy and is very susceptible to being broken

02

Acid hydrolysis of  1, 3 dioxane

1, 3 dioxanes on acidic hydrolysis forms methanal (formaldehyde).

Mechanism for acidic hydrolysis of 1, 3 dioxanes.

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Most popular questions from this chapter

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.

Ethyl p-nitrobenzoate has been found to undergo saponification faster than ethyl p-methoxybenzoate.

(a) Consider the mechanism of saponification, and explain the reasons for this rate enhancement.

(b) Would you expect ethyl p-methoxybenzoate to undergo saponification faster or slower than ethyl benzoate?

Show how Fischer esterification might be used to form the following esters. In each case, suggest a method for driving the reaction to completion.

(a) methyl salicylate

(b) methyl formate (bp 32掳C)

(c) ethyl phenylacetate

When pure (S)-lactic acid is esterified by racemic butan-2-ol, the product is 2-butyl lactate, with the following structure:

(a)Draw three-dimensional structures of the two stereoisomers formed, specifying the configuration at each asymmetric carbon atom. (Using your models may be helpful.)

(b)Determine the relationship between the two stereoisomers you have drawn.

Question: Suppose you have just synthesized heptanoic acid from heptan-1-ol. The product is contaminated by sodium dichromate, sulfuric acid, heptan-1-ol, and possibly heptanal. Explain how you would use acid-base extractions to purify the heptanoic acid. Use a chart, like that in Figure 20-3, to show where the impurities are at each stage.
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