Amines : amino group We functional group-NR2 attached to amine carbon

atoms .

Amines based on substitutional patterns of the amine carbon .

H H R
H
I & I
H -
N -
H R N H
- -
R2-N- R R-N -
R

Ammonia 1 amine 20 amine 30 amine

I primary (secondary (tertium)
Physical properties :
-
Two Imp properties of amines results from N-H... N
hydrogen bonding
·

boiling point *
Oxygen is more electronegative man
·

solubility/miscibility in water
hydrogen+so oxygen is better o
I hydrogen bond a limit hydrogen bonding than hydrogen.
-

-
is ,

one lone pair :

Ihydrogen ↓

water has 2 abilities for hydrogen oxygen is better than nitrogen.

DUIVS .

·
Amines are better to dissolve wh hydrogen bunding thun by themselves .

hydrogen bonding usually wins bic of how strong it is .

but sometimes more dispersion forces Can beat hydrogen bonding .

Naming Primary Amines

*rule of
① name longest chain containing NR2 functional group Oxidation still
② change-and to-anamine applies here .
I the end that will give the amine group the lowest #
4 carboxyl group wins bi it is more oxidized , soyor will have to

put that first before an amine . group

* Name starts
becoming important when the most oxidized group. Theyhend
N go first then the least oxidized.

CH3-NH2 CHgCH, CH2-NH2 CHz(H2CH2CHCH3

methamine
Niz
I-propamine
2-pentamine

Naming secondary and secondary Amines :

) convert chains
name of smaller to the prefix "N-alky)"
2143 CH2CH3
CHz-NH-CH2CH3 CH3-N-CH3 HzC-N-CHzCHz
↓ ↓ ↓
N-Methylethanamine N , N-Dimethylmethamine N iN-ethylmethyl ethanamine
Naming Amines : Common Names

naming the alkys group attached to the N In alphabetical order,

then add amine .
CH3
I

CHz
-

NHz CH3-NH-CH3 (H3-N-CHz CHzCH2-NH2

methylamine dimethylamine trimethylamine ethylamine

CHz(H2-NH CH3 .

Naming Aromatic Amines:

ethylmethylamine ① change base to benzenamine

②
Common name is aniline
& common memyl-substituted (toluenes) are
NH2 NH2 tolvidines .
NHz
NH+ 2

I CH3
(
I

2
2
3
benzenamine O-tolvidine CH3
↓ M-toluidine CH3
Ortho Cones ↓
p-folvidines
Name to structure : meth (twos ↓
para (three
. nexamine
3 N , N-diethyl-hexanamine
E + ↑ H

T
H - -

C C H
HH
-
-

H
If H((HH
I it
111111
H -
C C c
- - -
c -
C -
C -
H
11111
I I H IHH
. Chloro-N-memyl Cyclohexanamine
3 3-chlorobencanamine
M-chloroaniline
HN-CH3 It N NH2

-(H)
CHI
I
CHI
%-
CH)
- Cl
Ca
H
Societal uses : common in pharmaceuticals
·
most amines smell like ammonia . benzendrine
amphetamines stimulate the central nervous system . methedrine
·

analgestic : Acts as a pain relievers ; anesthetics act as pain blockers.

-

) curse nerves to be less reactive more dead -

.

Mey don't have hydrogen bunding. Amphetamines do have hydrogen

bunding .

analgesics : novacalne procaine demerl

common , ,

unsubstituted benzene higher chance to get cancer

= .

substituted benzene = your chances don't Increase stay the same , .

decogestants : shrink membrane lining in nusal passage .

note : Structural similarity blu ephedrine/pseudophedrine and

methamphetamine .

common seen : ephedune, pseudoephrine phenylephrine . ,

end to be isomers cause theyfend to be mirror

Images of each other but can have diff effects
from one another.

balthough these don't have much chemical differences bic all

are decogestants

Preparing Amines :
Reduction : addition of
hydrogen atoms .

R2 * R2 and R3 may
i R2 [H]
> RICHIN be a hydrogen
R -
C -
N R' atom or an
-
R3 organic group .
Amine Amine

O CH3
It [H]
>
i4HS [H]
> CHyCHzNCHs
CH3 (NH2 CH3CH2NH2 CHz)-NCH3
NIN-Dimethys -
ethanamide ethanamine .N-Dimethyl-
N ethanamine
lethylamine ethanamide

On-o
H
H (N(2)
(NO2)
- -
N

[H]
2 O
Derivatizing Amines :
Amines as Bronsted. Lowry Bases : He acceptors
H
H
R -
N : + H - OH
-
CHz -N + -
H + OH-

ion
it
water
# hydroxide

methyamine methylammonium
ion
H H

N
(
R - : + HC) < R -
N +
-
HC

it it
Amine acid Alkylammonium salt

+ - + - 2. + H-OH

it hydroxide it
ion water
alkylammonium Amine
SUlt

Quanternary ammonium salts

Quanternary Ammonium salts :
·
ammonium salts that have four organic
groups bonded to the nitrogen .

O
CH3 1/
Cl- O
CHy-N CH2CH2 Ol
CHSN
+ -

+
-
inty
CH3
choline
g num
Essential nutrient converted
In the body toPetylcholine

Heterocyclic amines :
Heterocyclic amines = Cyclic compound that has at least one w intering.
Aliphatic Heterocyclic Aromatic Heterocyclic

in

N .
 Societal Uses : (Alkaloids (
-
LSD -

nicotine -
Strychnine
-
cocaine -

Morphine , codeine , new in

-
Vitamin BD -
Quinine

Amides:
·

Amides contain carbamoys functional group (1 0)NR2 - =

·
amide is a combination of a carboxylic acid and an amine .

From carboxylic acid - i > From

-
amine
(Ar) R C - -

NH2
↓

ethanumide
Physical properties of Amides :
-
Amides have 2 physical properties that results from N-H ...
0

hydrogen bonding :

① boiling points are higher than amines lower than alcohol

,

& Solubility/miscibility In water are good for small amides

and bad in big
.
Naming Amides
& base name from longest Chain containing the (C =0)N2 -

② change-are to -anamide
& # from the end that will give the carboxyl carbon the lowest #

i
⑧

CHzC NH2 -
CHzCHac -
NHL
ethanoic acd propanoic acid
L N
ethanamide propanamide

Preparing Amides :
·

Acyl group transfer :

O P
D Il Il
R -
C Cl - +
2NHz
> R -
C -
NHz + NHcTCl-
Acid ammonia amide ammonium
Chloride Op Chloride
amine Or

alkyl -

ammonium
chloride
 Yo11 O O
1 Il
② R - C -
0 -
c R
-
+ 2NH3 > R -
C
NH2 -
+ R-c- 0- NHy
acid Amide
-

ammonia carboxylic acid

anhydride Or Salt
amine
Derivatizing amides :
hydrolysis : reactions blu amides and water in acid or base solutions .

P P t
R C
-
-

NH -12 +
Hz0" > R
- -
C -
OH + R1 -

NHz
amide Strong carboxylic Alkylammoniumion
acid acid ammonium ion