Aminas Y Amidas

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R – NH2

R – C – NH2 || O

QUÍMICA IV AMINAS Y AMIDAS GRUPOS FUNCIONALES

GRUPO FUNCIONAL AMINA Par electrónico solitario

N

H 105.9°

° 13

1

H

R

° 3 2

124° 11



N

H

R

C

1

O

GRUPO FUNCIONAL AMIDA

H

119 °

MÉTODOS DE OBTENCIÓN (1) AMINAS: REDUCCIÓN DE COMPUESTOS NITRO:

(Ar) R NO2 NO2

CH3 CH2 NO2

(Ar) R reductores

reductores

NH2 NH2 + 2 H2O

CH3 CH2 NH2 + 2 H2O

MÉTODOS DE OBTENCIÓN (2) REDUCCIÓN DE NITRILOS (Ar) R C

CH3 C

N

N

C N

reductores

reductores

reductores

(Ar) R CH2 NH2

CH3 CH2 NH2

CH2 NH2

PROPIEDADES QUÍMICAS (1) REACCIÓN DE AMINAS CON HALURO DE ALQUILO R’ X R NH2 +

R’ X

R NH R’ + HX

R N R’2 + HX R’ X

R N+ R’3 XCH3Br CH3 CH2 NH2 + CH3Br

CH3 CH2 NH CH3 + HBr

CH3-CH2-N+(CH3)3-Br– CH -BrCH3 -CH2 –N- (CH3)2 + HBr 3

PROPIEDADES QUÍMICAS (2) REACCIÓN CON ÁCIDO NITROSO (Ar) R - NH2 + NaNO2 + HX NH2 + NaNO2 + HCl

Ar (R) – N = N+X-

N = N+X SAL DE DIAZONIO

CH3 – CH2 – NH2 + NaNO2 + HCl

CH3 - CH2 – N = N+Cl-

MÉT ODOS DE OBTE NC IÓN (1) AMIDAS REACCIÓN DE CLORURO DE ACILO Y AMONÍACO + HCl R C Cl || O

NH3 NH4OH

CH3 - CO.Cl + NH4OH

R C NH2 || O

+ HCl + H2O

CH3 - CO.NH2 + HCl + H2O

MÉTODOS DE OBTENCIÓN (2) REACCIÓN ENTRE ÁCIDOS Y AMONÍACO R – CO.OH + NH3 CH3 – CH2 – CO.OH + NH3

R – CO.ONH4

CALOR

R – CO.NH2 + H2O

CH3 – CH2 – CO.ONH4

CH3 – CH2 – CO.NH2 + H2O H – CO.OH + NH3

H – C – O.ONH4

CALOR

H – CO.NH2 + H2O

PROPIEDADES QUÍMICAS (1) DESHIDRATACIÓN DE AMIDAS: 3 (Ar) R – CO.NH2 + POCl3 3CH3 – CO.NH2 + POCl3 CO.NH2

+ POCl3

3 (Ar) R – C 3 CH3 – C

N

N + H3PO4 + 3 HCl + H3PO4 + 3HCl

C N

+

H3PO4 + 3HCl

PROPIEDADES QUÍMICAS (2) HIDRÓLISIS DE AMIDAS + NH3

H

+

R – CO.NH2

+ H2O

CH3 – CO.NH2 + H2O + H+

OH

R – CO.OH –

+ NH4OH CH3 – CO. OH + NH3

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