Dolbier HW Solutions 362

Dolbier HW Solutions 362 - CH 3 (CH 2 ) 8 CH CHCH 2 CH CHCH...

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( e ) Oxidative cleavage of the alkene yields benzophenone. Ozonolysis may be used. 17.38 The two alcohols given as starting materials contain all the carbon atoms of the desired product. What is needed is to attach the two groups together so that the two primary alcohol carbons become doubly bonded to each other. This can be accomplished by using a Wittig reaction as the key step. Alternatively, allyl alcohol could be oxidized to CH 2 ? CHCHO for subsequent reaction with the ylide derived from CH 3 (CH 2 ) 8 CH ? CHCH 2 CH ? CHCH 2 CH 2 OH via its bromide and triphenyl- phosphonium salt. 17.39 The expected course of the reaction would be hydrolysis of the acetal to the corresponding aldehyde. 1 H 2 O HCl C 6 H 5 CHCH(OCH 3 ) 2 OH Compound A (mandelaldehyde dimethyl acetal) C 6 H 5 CHCH OH O Mandelaldehyde 2CH 3 OH Methanol O CHCH 2 CH CHCH 2 CH CH 3 (CH 2 ) 8 CH 3,6-Hexadecadienal Allylidenetriphenylphosphorane 1,3,6,9-Nonadecatetraene
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Unformatted text preview: CH 3 (CH 2 ) 8 CH CHCH 2 CH CHCH 2 CH CHCH CH 2 1 CH 2 (C 6 H 5 ) 3 P 1 2 CHCH Allyltriphenylphosphonium bromide Allylidenetriphenylphosphorane (C 6 H 5 ) 3 P H 2 C CHCH 2 Br H 2 C CHCH 2 OH Allyl alcohol Allyl bromide PBr 3 CH 3 CH 2 CH 2 CH 2 Li, THF (C 6 H 5 ) 3 PCH 2 CH CH 2 Br 2 1 (C 6 H 5 ) 3 P CH 2 CHCH 2 1 CHCH 2 CH CH 3 (CH 2 ) 8 CH CHCH 2 CH 2 OH 3,6-Hexadecadien-1-ol 3,6-Hexadecadienal PCC CH 2 Cl 2 CHCH 2 CH CH 3 (CH 2 ) 8 CH CHCH 2 CH O CH 2 CHCH CHCH 2 CH CH 3 (CH 2 ) 8 CH CHCH 2 CH 3,6-Hexadecadien-1-ol Allyl alcohol CH 3 (CH 2 ) 8 CH CHCH 2 CH CHCH 2 CH 2 OH and HOCH 2 CH CH 2 1. O 3 2. H 2 O, Zn 1,1,2,2-Tetraphenylethene 2(C 6 H 5 ) 2 C O Benzophenone (C 6 H 5 ) 2 C C(C 6 H 5 ) 2 456 ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION TO THE CARBONYL GROUP...
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