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Other Reducing Agents: H / Ni 140 C Na / Ethanol: Amines Compound

This document provides information about amines, including their preparation, naming, properties, and uses. It discusses several methods for preparing amines, such as reduction of nitrocompounds, reduction of amides, and Hofmann degradation of amides. It notes that amines can be primary, secondary, or tertiary depending on the number of alkyl or aryl groups attached to the nitrogen. The document explains that amines are soluble in water due to hydrogen bonding and that aromatic amines are usually liquids with high boiling points. It also describes amines as being both Brønsted and Lewis bases and discusses how their basicity can be altered by substituents. Amines are further characterized as weak acids. Common bases used

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0% found this document useful (0 votes)
27 views

Other Reducing Agents: H / Ni 140 C Na / Ethanol: Amines Compound

This document provides information about amines, including their preparation, naming, properties, and uses. It discusses several methods for preparing amines, such as reduction of nitrocompounds, reduction of amides, and Hofmann degradation of amides. It notes that amines can be primary, secondary, or tertiary depending on the number of alkyl or aryl groups attached to the nitrogen. The document explains that amines are soluble in water due to hydrogen bonding and that aromatic amines are usually liquids with high boiling points. It also describes amines as being both Brønsted and Lewis bases and discusses how their basicity can be altered by substituents. Amines are further characterized as weak acids. Common bases used

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AMINES COMPOUND

RCN

RNH2
o
1 amine

LiAlH4
dry ether

RCH2NH2

RNHR'
o
2 amine

RNR'R"
3oamine

Other reducing agents:


H2 / Ni 140oC
Na / ethanol
From acid nitrite

R'
+
R N R"
R'"
quaternary
ammonium salt

PREPARATION OF AMINES

Reduction from nitrocompound

NO2

O
R

From acids amide

NH2

LiAlH4

RCH2NH2

Sn / conc. HCl

NH2

LiAlH4 / dry ether

RNO2

RNH2

From (Hofmann degradation)

Other reducing agents:


KOH / Br
RNH
Sn
/
conc.
HCl; H2 / Ni
C NH
O

With
fishysmell.

It will reduce 1 carbon atom in this reaction.


Physical
Soluble in water due to HPROPERTIES OF
AMINE

bond formation.
Aromatic amine are liquid
with high boiling point

methanamine

N-methylethanamine
2-methyl propan-2-amine
NAMING AMINE

CH3NH2
(CH3)3CNH2
CH3CH2NHCH3

CHEMICAL
PROPERTIES OF
AMINES
Acidity of Amines
Basicity of Amines

Important Reagent
Bases

most amines are Brnsted and Lewis bases,

1 and 2-amines are also very weak

Most base reagents are

but their base strength can be changed

acids (ammonia has a pKa = 34). In this

alkoxide salts, amines or amide

enormously by substituents. It is common to

respect it should be noted that pKa is

salts. Since alcohols are much

compare basicity's quantitatively by using

being used as a measure of the acidity

stronger acids than amines,

the pKa's of their conjugate acidsrather than

of the amine itself rather than its

their conjugate bases are

their pKb's. Since pKa + pKb = 14, the higher

conjugate acid, as in the previous

weaker than amide bases, and

the pKa the stronger the base, in contrast to

section. For ammonia this is expressed

fill the gap in base strength

the usual inverse relationship of pKa with acidity.

by the following hypothetical equation:

between amines and amide


salts.

NH3 + H2O

____

> NH2() + H2O-H(+)

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