12.3.2.4 To form amideRCOOH + NH3RCOONH4+RCONH,+HO
12.3.2.4 To form amide RCOOH + NH3 RCOO - NH4 RCONH2 + H2 O
12.3.3 Reduction of carboxylic acid12.3.3.1 By LiAIH4H.O乙醚2CHCH2CHCOOH +LiAIH2CH3CH2CHCH2OH+LiAIO2CH3CH383%
12.3.3 Reduction of carboxylic acid 12.3.3.1 By LiAlH4 2 CH3CH2CHCOOH + LiAlH4 CH3 乙醚 H3O 2 CH3CH2CHCH2OH + LiAlO2 CH3 83%
12.3.3.2 By boraneH.OTHF2PhCOOH + B,He2 PhCH2OH + 2H2+ 2B(OH)389%福-UH:OB2H6C2H,OC(CH2)4C0OHC2H,0C(CH2)4CH2OHTHF88%乙硼烷的还原能力：-COOHC=O>—CN>—COOR>-COCI
12.3.3.2 By borane 2 PhCOOH + B2H6 THF H3O 2 PhCH2OH + 2 H2 + 2 B(OH) 3 89% C2H5OC(CH2) 4 COOH O B2H6 THF H3O C2H5OC(CH2) 4 CH2OH O 88% COOH > C O > C N > COOR > COCl 乙硼烷的还原能力：
12.3.4 Reaction with organometalliccompoundsCOOHH.oCH32 CH3Li乙醚CH3CH3
12.3.4 Reaction with organometallic compounds COOH CH3 2 CH3 Li 乙醚 H3 O C CH3 CH3 O
mechanism:0O11RC-O-Li+ CH4R-COH + LiCH3-OLiOHH:0-R-C-OLiR-C-OH + 2Lit-OLi + LiCH3CH3CH30OH1R-C-OH→R-CCH3 + HOCH3
mechanism： R COH + LiCH3 O RC O O Li + CH4 R C OLi + LiCH3 O R C OLi OLi CH3 H3O R C OH CH3 OH + 2 Li R C OH OH CH3 R CCH3 + H2O O