Dolbier HW Solutions 323

Dolbier HW Solutions 323 - 417 ETHERS, EPOXIDES, AND...

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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 the same molecule. It contains the requisite functionality to undergo an intramolecular Williamson reaction. 16.33 ( a ) The f rst 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 to yield the vicinal dibromide. When compound B is treated with potassium hydroxide, it loses the elements of HBr to give compound C. Because further treatment of compound C with potassium hydroxide converts it to D by a second dehydrobromination, a reasonable candidate for C is 3-bromotetrahydrofuran.
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This note was uploaded on 09/28/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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