Dolbier HW Solutions 485

Dolbier HW Solutions 485 - 2 5 CH 2 CH(COOCH 2 CH 3 2...

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( c ) The disconnection approach to retrosynthetic analysis reveals that the preparation of 5-hexen- 2-one by the acetoacetic ester synthesis requires an allylic halide. 21.7 ( b ) Nonanoic acid has a CH 3 (CH 2 ) 5 CH 2 @ unit attached to the synthon. Therefore the anion of diethyl malonate is alkylated with a 1-haloheptane. ( c ) Disconnection of the target molecule adjacent to the a carbon reveals the alkyl halide needed to react with the enolate derived from diethyl malonate. 1 Derived from diethyl malonate CH 2 COH O 2 Required alkyl halide CH 3 CH 2 CHCH 2 X CH 3 CH 3 CH 2 CHCH 2 O CH 2 COH CH 3 1 1-Bromoheptane CH 3 (CH 2 ) 5 CH 2 Br Diethyl malonate CH 2 (COOCH 2 CH 3 ) 2 Diethyl 2-heptylmalonate CH 3 (CH
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Unformatted text preview: 2 ) 5 CH 2 CH(COOCH 2 CH 3 ) 2 Nonanoic acid CH 3 (CH 2 ) 5 CH 2 CH 2 CO 2 H NaOCH 2 CH 3 ethanol 1. HO 2 , H 2 O 2. H 1 3. heat 1 Derived from diethyl malonate CH 2 COH O 2 Required alkyl halide CH 3 (CH 2 ) 5 CH 2 X CH 3 (CH 2 ) 5 CH 2 O CH 2 COH CH 2 COH O 1 Allyl bromide CHCH 2 Br H 2 C 5-Hexen-2-one CHCH 2 CH 2 CCH 3 O H 2 C Ethyl acetoacetate CH 3 CCH 2 COCH 2 CH 3 O O 1. NaOCH 2 CH 3 2. HO 2 , H 2 O 3. H 1 4. heat 1 Required alkyl halide CHCH 2 H 2 C X Derived from ethyl acetoacetate CH 2 CCH 3 O 2 H 2 C CHCH 2 O CH 2 CCH 3 ESTER ENOLATES 579...
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