Dolbier HW Solutions 529

Dolbier HW Solutions 529 - isopropyl alcohol. Acetone CH 3...

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( b ) The carbon chain of tert -butyl chloride cannot be extended by a nucleophilic substitution reaction; the S N 2 reaction that would be required on the tertiary halide would not work. The sequence employed in part ( a ) is therefore not effective in this case. The best route is car- boxylation of the Grignard reagent and subsequent conversion of the corresponding amide to the desired primary amine product. The reaction sequence to be used is Once the carboxylic acid has been obtained, it is converted to the desired amine by reduction of the corresponding amide. ( c ) Oxidation of cyclohexanol to cyclohexanone gives a compound suitable for reductive amination. ( d ) The desired product is the reduction product of the cyanohydrin of acetone. The cyanohydrin is made from acetone in the usual way. Acetone is available by oxidation of
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Unformatted text preview: isopropyl alcohol. Acetone CH 3 CCH 3 O Acetone cyanohydrin CH 3 CCH 3 OH CN KCN H 2 SO 4 Isopropyl alcohol CH 3 CHCH 3 OH K 2 Cr 2 O 7 , H 2 SO 4 H 2 O Acetone cyanohydrin CH 3 CCH 3 OH CN 1-Amino-2-methyl-2-propanol CH 3 CCH 3 OH CH 2 NH 2 1. LiAlH 4 2. H 2 O Cyclohexanol OH N-Methylcyclohexylamine NHCH 3 Cyclohexanone O K 2 Cr 2 O 7 H 2 SO 4 , H 2 O CH 3 NH 2 , H 2 , Ni or CH 3 NH 2 , NaBH 3 CN (CH 3 ) 3 CCO 2 H 2,2-Dimethylpropanoic acid (CH 3 ) 3 CCH 2 NH 2 2,2-Dimethyl-1-propanamine 2,2-Dimethylpropanamide (CH 3 ) 3 CCNH 2 O 1. SOCl 2 2. NH 3 1. LiAlH 4 2. H 2 O 1. Mg, diethyl ether 2. CO 2 3. H 3 O 1 (CH 3 ) 3 CCl tert-Butyl chloride (CH 3 ) 3 CCO 2 H 2,2-Dimethylpropanoic acid (CH 3 ) 3 CCH 2 NH 2 (CH 3 ) 3 CCO 2 H (CH 3 ) 3 CCNH 2 O (CH 3 ) 3 CCl AMINES 623...
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