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Chapter 14: Q5P (page 716)

1,4-Dioxane is made commercially by the acid-catalyzed condensation of an alcohol.

(a)Show what alcohol will undergo condensation, with loss of water, to give 1,4-dioxane.

(b)Propose a mechanism for this reaction

Short Answer

Expert verified

(A) Reaction between ethylene glycol in presence of acid to give dioxane



(B) Mechanism for the above reaction is

Step by step solution

01

Step 1: 

Dioxanesare ethers with two oxygen atoms in a six-membered ring. The most useddioxane is the one with the two oxygenatoms in a 1,4-relationship (1,4-dioxane). Dioxane usedas a polar solvent for organic reactions.

02

Step 2

In mechanism first step is protonation and removal of a water molecule from ethylene glycol. In the second step another ethylene glycol attacks this protonated molecule. In the last step removal of a water molecule to give 1,4-dioxane.

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