Dolbier HW Solutions 575

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

Info iconThis preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
( 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.
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

{[ snackBarMessage ]}

Ask a homework question - tutors are online