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Consider the three constitutional isomers of dioxane

Chapter 20, Problem 20.74

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QUESTION:

Consider the three constitutional isomers of dioxane (C4H8O2): O O 1,2-Dioxane O O 1,3-Dioxane O O 1,4-Dioxane One of these constitutional isomers is stable under basic conditions as well as mildly acidic conditions and is therefore used as a common solvent. Another isomer is only stable under basic conditions but undergoes hydrolysis under mildly acidic conditions. The remaining isomer is extremely unstable and potentially explosive. Identify each isomer and explain the properties of each compound.

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QUESTION:

Consider the three constitutional isomers of dioxane (C4H8O2): O O 1,2-Dioxane O O 1,3-Dioxane O O 1,4-Dioxane One of these constitutional isomers is stable under basic conditions as well as mildly acidic conditions and is therefore used as a common solvent. Another isomer is only stable under basic conditions but undergoes hydrolysis under mildly acidic conditions. The remaining isomer is extremely unstable and potentially explosive. Identify each isomer and explain the properties of each compound.

ANSWER:

Step 1 of 2

This question asks us to consider the three constitutional isomers of dioxane:

                                             

We’re told that one of these isomers is stable under both basic and acidic conditions. Another of the isomers is stable towards base, but not acid. The remaining isomer is extremely unstable and potentially explosive. We’re asked to match the isomers to their described properties.

 

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