Dolbier HW Solutions 575

Dolbier HW Solutions 575 - 669 ARYL HALIDES (b) The same...

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( b ) The same Meisenheimer complex results when ethyl 2,4,6-trinitrophenyl ether reacts with sodium methoxide. 23.26 Methoxide ion may add to 2,4,6-trinitroanisole either at the ring carbon that bears the methoxyl group or at an unsubstituted ring carbon. The two Meisenheimer complexes are the sodium salts of the anions shown. It was observed that compound A was the more stable of the two. Compound B was present immediately after adding sodium methoxide to 2,4,6-trinitroanisole but underwent relatively rapid isomerization to compound A. 23.27 ( a ) The f rst reaction that occurs is an acid base reaction between diethyl malonate and sodium amide. A second equivalent of sodium amide converts bromobenzene to benzyne. The anion of diethyl malonate adds to benzyne. This anion then abstracts a proton from ammonia to give the observed product.
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This note was uploaded on 10/03/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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