There are three dioxane isomers: 1,2-dioxane, 1,3-dioxane,

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L. G. Wade Jr

Problem 61SP Chapter 18

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L. G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 61SP

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 solvent 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 explain why one of them is potentially explosive. Propose a mechanism for the acid hydrolysis of the third isomer.

Step-by-Step Solution:
Step 1 of 3

Here we have to show which isomer that acts like a simple ether (among the three given ethers) and explain why one of them is potentially explosive. Then we have to propose a mechanism for the acid hydrolysis of the third isomer (1,4-dioxane).

Step-1

Among the three given dioxanes (ethers), the difference is the position of the oxygen atom.

In 1,2-dioxane, the two O-O bond is connected by a sigma bond (peroxide). The O-O can easily break and form  radicals .

In 1,3-dioxane , the two oxygens bonded to a sp3 C-atom constitute an acetal. It can be hydrolyzed in aqueous...

Step 2 of 3

Chapter 18, Problem 61SP is Solved
Step 3 of 3

Textbook: Organic Chemistry
Edition: 8
Author: L. G. Wade Jr
ISBN: 9780321768414

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There are three dioxane isomers: 1,2-dioxane, 1,3-dioxane,

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