To propose a plausible synthesis for 1 , 4 − dioxane , starting with acetylene as the only source of carbon atoms. Concept introduction: The retrosynthesis begins with disconnection at the ether groups, at two of the C–O bonds, thereby breaking up the structure into two fragments, each with two carbon atoms. The more electronegative oxygen atom is more likely to have served as the nucleophile, so a negative charge on the oxygen atom has been drawn to give a suitable nucleophile (alkoxide ion). The carbon atom (at the disconnected bond) must have started out as an electrophile, so a leaving group (such as Cl , Br , I or OTs ) at that position has been drawn: Each of these starting materials can be made from acetylene.

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Chapter 11, Problem 37IP

Interpretation Introduction

Interpretation: To propose a plausible synthesis for 1,4− dioxane , starting with acetylene as the only source of carbon atoms.

Concept introduction: The retrosynthesis begins with disconnection at the ether groups, at two of the C–O bonds, thereby breaking up the structure into two fragments, each with two carbon atoms. The more electronegative oxygen atom is more likely to have served as the nucleophile, so a negative charge on the oxygen atom has been drawn to give a suitable nucleophile (alkoxide ion). The carbon atom (at the disconnected bond) must have started out as an electrophile, so a leaving group (such as Cl , Br , I or OTs) at that position has been drawn:

Each of these starting materials can be made from acetylene.

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