Aliphatic amines part III
- 2. REACTIONS OF ALIPHATIC AMINES Alkylation Reaction Hofmann’s Reaction Acylation Reaction with nitrous acid Carbylamine formation Oxidation Reaction with Grignard reagent
- 3. Alkylation of amines R NH2 R2NH R3N R4NH X -+ RX+RX -HX +RX -HX primary amine secondary amine tertiary amine quartenary ammonium salt C6 5 H NH2 + CH3I C6 5 H NHCH3 + HI aniline methyl aniline C6 5 H NHCH3 + CH3 I methyl aniline C6H5 N(CH3)2 + HI N,N-Dimethyl aniline
- 4. Hofmann’s elimination R4N X -+ R4 N OH -+ + AgX 3HC N CH3 CH3 CH2CH2CH2OH - NH3C CH3 CH3 + CH2 CH CH3 + H2O propene trimethyl aminetrimethyl n propyl ammonuim hydroxide
- 5. Acylation of amines RNH2 + R'COCl R'CONHR + HCl acid chloride RNH2 + C6H5SO2Cl C6H5SO2NHR + HCl R2NH + CH3SO2Cl C6H5SO2NR2 + HCl C2H5NH2 + CH3COCl C2H5NHCOCH3 + HCl phenyl sulphonyl chloride n ethyl acetamide ethylamine acetyl chloride (CH3)2NH + C6H5COCl (CH3)2NCOC6H5 + HCl N,N-Dimethyl benzamide NH2 CH3 + (CH3CO)2O + CH3COOH NHCOCH3 CH3
- 6. Reaction with Nitrous acid R NH2 + HONO ROH + N2 + H2O C2H5NH2 + HONO C2H5OH + N2 + H2O R2NH2 + HONO R2N N O + H2O eg: eg: (CH3)2NH + HONO (CH3)2N N O + H2O primary amine secondary amine
- 7. C6H5 NH CH3 + HONO C6H5 N N O CH3 + H2O N-Nitroso N methyl aniline N-methylaniline R3N + HNO2 R3NHNO2 tertiary amine
- 8. Carbylamine reaction C2H5NH2 + CHCl3 + KOH C2H5NC + 3KCl + 3H2O ethyl amine chloro form carbylamine R NH2 + S C S HgCl2 R NH C S + H2S alkylisothio cyanate R2NH + S C S S C SH NR2 mustard oil reaction
- 9. oxidation R CH2NH2 R KMnO4 (O) CH NH H2O RCHO + NH3 R H C NH2R' KMnO4 (O) R C NH R' R C O R' + NH3 KMnO4 (O) 2R2NH R N N R R R tertra alkyl hydrazine + H2O primary amine secondary amine R N R R H2O2 (O) R3 O + _ amine oxide tertuary amine
- 10. Reaction with Grignard reagent RNH2 + R'MgX RNHMgX + R'H alkanegrignard reagent R NH R + R'MgX R'H + R NMgX R + R'H
- 11. LETS GO AHEAD & SEE AGAIN