Dolbier HW Solutions 576

Dolbier HW Solutions 576 - product. F F F F F OCH 2 CH 2 OH...

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( b ) The ester is deprotonated by the strong base sodium amide, after which the ester enolate under- goes an elimination reaction to form a benzyne intermediate. Cyclization to the f nal product occurs by intramolecular attack of the ester enolate on the reactive triple bond of the aryne. ( c ) In the presence of very strong bases, aryl halides undergo nucleophilic aromatic substitution by an elimination addition mechanism. The structure of the product indicates that a nitrogen of the side chain acts as a nucleophile in the addition step. ( d ) On treatment with base, intramolecular nucleophilic aromatic substitution leads to the observed
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Unformatted text preview: product. F F F F F OCH 2 CH 2 OH F F F F O O F F F F F OCH 2 CH 2 O 2 O O F F F F F 2 K 2 CO 3 heat NaNH 2 ether NaNH 2 , NH 3 NH 3 NCH 2 CH 2 NHCH 3 Cl CH 3 NCH 2 CH 2 NCH 3 Cl CH 3 2 CH 3 CH 3 N 2 N CH 3 CH 3 N N N CH 3 CH 2 CH 2 N CH 3 2 NaNH 2 NH 3 NaNH 2 CH 2 CH 2 CH 2 CH 2 COCH 2 CH 3 Cl O Ethyl 5-(2-chlorophenyl)pentanoate Ester enolate CH 2 CH 2 CH 2 CHCOCH 2 CH 3 Cl O 2 COOCH 2 CH 3 CH 2 CH 2 CH 2 CH COOCH 2 CH 3 2 Aryne intermediate COOCH 2 CH 3 Ethyl 1,2,3,4-tetrahydronaphthalene-1-carboxylate 2 670 ARYL HALIDES...
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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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