432 ALDEHY DES AND KETONES: NUCLEOPHI ON TO THE CARBONYL GROUP 17.11(b) Nucleophilic addition of butylamine to benzaldehyde gives the carbinolamine OH -CH CH..CHNH CH-NCHCH.CH Carbinolamine intermediate Dehydration of the carbinolamine produces the imine CH— NCH CHCH CH =NCH, CH, CH, CH3 (c) Cyclohexanone and tert-butylamine react according to the equation HO NC(CH, NC(CH 3)3 +( Ch3)cNH Cyclohexanone tert-Butylamine Carbinolamine N-Cyclohexylidene- intermediate NH C6H CCH3+ C6HSCCH3 -H,O C6HSCCH3 Carb 17.12 (b) Pyrrolidine, a secondary amine, adds to 3-pentanone to give a carbinolamine CHa CH,CCH, CH3 CHCH, CCH, CH3 3-Pentanone Pyrrolidine Dehydration ices the enamine CHCH,CCH,CH CH CHECCHCH hO Carbinolamine Back Forward Main Menu TOC Study Guide Toc Student OLC MHHE Website17.11 (b) Nucleophilic addition of butylamine to benzaldehyde gives the carbinolamine. Dehydration of the carbinolamine produces the imine. (c) Cyclohexanone and tert-butylamine react according to the equation (d) 17.12 (b) Pyrrolidine, a secondary amine, adds to 3-pentanone to give a carbinolamine. Dehydration produces the enamine. Carbinolamine 3-Pyrrolidino-2-pentene intermediate CH3CH2CCH2CH3 OH H2O N CH3CH CCH2CH3 N 3-Pentanone CH3CH2CCH2CH3 O Carbinolamine intermediate CH3CH2CCH2CH3 OH Pyrrolidine H N N Acetophenone Carbinolamine Cyclohexylamine intermediate C6H5CCH3 OH NH NH2 C6H5CCH3 O N-(1-Phenylethylidene)- cyclohexylamine C6H5CCH3 N H2O H2O O Cyclohexanone HO NC(CH3)3 H Carbinolamine intermediate (CH3)3CNH2 tert-Butylamine NC(CH3)3 N-Cyclohexylidene￾tert-butylamine N-Benzylidenebutylamine CH NCH2CH2CH2CH3 OH H H2O CH NCH2CH2CH2CH3 Carbinolamine intermediate CH CH3CH2CH2CH2NH2 O Benzaldehyde Butylamine CH NCH2CH2CH2CH3 OH H 432 ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION TO THE CARBONYL GROUP Back Forward Main Menu TOC Study Guide TOC Student OLC MHHE Website