Diethylene glycol then undergoes intramolecular ether formation to yield 1,4-dioxane.(b)The substrate is a primary alkyl halide and reacts with aqueous sodium hydroxide by nucle-ophilic substitution.The product of this reaction now has an alcohol function and a primary chloride built into thesame molecule. It contains the requisite functionality to undergo an intramolecularWilliamson reaction.16.33(a)The frst step is a standard Grignard synthesis of a primary alcohol using formaldehyde.Compound A is 3-buten-1-ol.Addition of bromine to the carbon–carbon double bond of 3-buten-1-ol takes place readily toyield the vicinal dibromide.When compound B is treated with potassium hydroxide, it loses the elements of HBr to givecompound C. Because further treatment of compound C with potassium hydroxide converts itto D by a second dehydrobromination, a reasonable candidate for C is 3-bromotetrahydrofuran.
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