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Dolbier HW Solutions 353 - intermediate C 6 H 5 CCH 3 O H 1...

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( b ) The reagent CH 3 ONH 2 is called O -methylhydroxylamine, and it reacts with aldehydes in a manner similar to hydroxylamine. ( c ) Propanal reacts with 1,1-dimethylhydrazine to yield the corresponding hydrazone. ( d ) Acid-catalyzed hydrolysis of the acetal gives the aldehyde in 87% yield. ( e ) Hydrogen cyanide adds to carbonyl groups to form cyanohydrins. ( f ) The reagent is a secondary amine known as morpholine. Secondary amines react with ke- tones to give enamines. ( g ) Migration of the alkyl group in a Baeyer Villiger oxidation occurs with retention of con fi guration. Peroxybenzoic acid O C 6 H 5 COOH ( R )-3-Methyl-3-phenyl-2- pentanone O H 3 C CCH 3 CH 3 CH 2 ( R )-1-Methyl-1-phenylpropyl acetate O H 3 C OCCH 3 CH 3 CH 2 HN O Acetophenone Morpholine Carbinolamine
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Unformatted text preview: intermediate C 6 H 5 CCH 3 O H 1 H 1 ( 2 H 2 O) C 6 H 5 CCH 3 OH O N 1-Morpholinostyrene (57 – 64%) C 6 H 5 C CH 2 O N NaCN HCl C 6 H 5 CCN OH CH 3 Acetophenone cyanohydrin C 6 H 5 CCH 3 O Acetophenone H 3 C CHCH 2 CH 2 CH 3 O O H 2 O, HCl heat H 3 C CHCH 2 CH 2 CH CH 3 O 4-( p-Methylphenyl)pentanal 1 (CH 3 ) 2 NNH 2 1,1-Dimethylhydrazine NN(CH 3 ) 2 CH 3 CH 2 CH Propanal dimethylhydrazone O CH 3 CH 2 CH Propanal 1 OCH 3 HO CH O 4-Hydroxy-2-methoxybenzaldehyde CH 3 ONH 2 O-Methyl-hydroxylamine OCH 3 HO CH NOCH 3 4-Hydroxy-2-methoxybenzaldehyde O-methyloxime ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION TO THE CARBONYL GROUP 447...
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