Bahan Ajar Amina
Bahan Ajar Amina
Bahan Ajar Amina
Amines
Amines are organic compounds in which one or more H in ammonia, NH3, is replaced with alkyl or aromatic groups.
H | HNH ammonia
H H | | CH3NH CH3NCH3
Classification of Amines
Amines are classified as primary, secondary, or tertiary. In a primary (1) amine, one carbon group is bonded to the nitrogen atom. A secondary (2) amine has two carbon groups. A tertiary (3) amine has three carbon groups. H CH3 CH3 | | | CH3NH CH3NH CH3NCH3 1 2 3
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Models of Amines
The three-dimensional models show the shapes of amine molecules with one or more alkyl groups bonded to the nitrogen atom.
CH3CH2NH2 Ethylamine
CH3NHCH3 Dimethylamine
Aromatic Amines
The amine of benzene is named aniline.
NH2 NH2 NH CH3
Cl
Aniline
3-Chloroaniline
N-Methylaniline
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Heterocyclic Amine:
N
Pyridine
N
Pyrole
N
Quinoline
N
Indole
N H
Pyrolidine
N H
Piperidine
LATIHAN
1. Beri nama sistematis atau nama umum serta klasifikasikan senyawa-senyawa amina di bawah ini menjadi amina primer, sekunder atau tersier
CH3CH2CH2NH2 CH3NHCH3 C6H5NH2 (CH3)2NC2H5
NH2
NH2
2-metil-1-butanamina
3-metil-3-pentanamina
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LATIHAN
2. Tuliskan struktur senyawa amina di bawah ini: a. Isopropilamina b. 3-pentanamina c. Siklopentanamina d. Fenilamina e. 2-metil-sikloheksanamina
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Solubility in Water
Amines with 1-5 carbon atoms are soluble in water. The N atom in amines forms hydrogen bonds with the polar O-H bond in water.
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Learning Check
Consider the following compounds: 1. CH3CH2CH2NH2 2. CH3CH2NHCH3 3. CH3CH2CH2CH3
A. Which compound has the highest boiling point? B. Which compound(s) is(are) soluble in water?
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CH3NH2 + H2O
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Learning Check
Write the equation for ethylamine when it reacts with each of the following: 1. + H2O
2. + HCl
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O C N K+ RCH 2 X
O C N CH 2 R C O O
Gabriel Synthesis
CH 2 R
OH /H 2 O
C O RCH 2 NH 2 + C O O
RCH 2 X + NH 3 RCH 2 NH 2
OH-
Alkylation
(RCH 2 )3 N
RCH 2 NHCH 2 R
RCH 2 X
(RCH 2 )4 N
CH3Cl
NH2 aniline
2 CH3CH2Br
Et N Et N,N-diethylaniline
Ar
HNO3 H H2SO4
Ar NO2
NH2
[ H]
Ar NH2
NO2
1) Fe, HCl 2) OH
CH2C
N + 2 H2
LiAlH4
Raney Ni 140
CH2CH2NH2
(71%)
N CH2CH3 CH3
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R (R')H
C O + NH3(or R''NH2)
H2, Ni
-H2O
R (R')H
C NH(R'')
R CH NH2(R'') (R')H
Imine
H C O + NH3
H2, Ni 90 atm 40 ~ 70
H2, Ni, EtOH 95
CH2NH2
(89%)
(CH3)2CNHCH2CH2OH
(CH3)2C O + H2NCH2CH2OH
1-(N-ethylamino)-1-phenylpropane
CH3NH2, H2/Ni
NHCH3
cyclohexanone
cyclohexylmethylamine
OH /H 2O
RNH
+ CO 2
+ R C N N N O
Acyl azide
H 2O
RNH
+ CO 2
+ N2
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R-NH2 + NaNO2
+ 2HCl
CH3CH2CH2NH2
Primary alkyl amines
NaNO2, HCl
CH3CH2CH2 N
diazonium salt
NCl
CH3CH2CH2 + N2 + HCl
carbocation
N Cl + H2O + NaCl
diazonium salt
Flowchart Reaction
A. Sandmeyer reaction B. Hydrolisis Primary amine Diazonium salt C. Deamination D. Azo coupling Alkyl halide/cyanide Alcohol
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p-Isopropylaniline
p-Isopropylphenol
(73%)
+ N2 :Electron-withdrawing group
OH
Br
C. Deamination
Aryl diazonium salts react with hypophosphorous acid (H3PO2)
D. Azo Coupling
Contain the -N=N- group. Result of a coupling
Azo group
Azo coupling
Aryl diazonium salts are weak electrophiles, they react with highly reactive aromatic compounds, to yield azo compounds
+ CH3COO -Na+ 0 H2O
N2 Cl +
N(CH3)2
N N
N(CH3)2
Azo dyes
Orange II
N N OH
SO3 Na
Tartrazine
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menyerap cahaya pada daerah UV-Vis sehingga menyebabkan senyawanya memiliki warna Salah satu gugus kromofor adalah ikatan rangkap terkonjugasi Maka, senyawa azo memiliki warna Maka, azo dapat dianalisis kadarnya dengan cara spektrofotometri
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TUGAS
Cari definisi, rumus umum dan contoh dari :
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Alkaloids
Alkaloids are Physiologically active nitrogen-containing compounds. Produced by plants. Used as stimulants, anesthetics, and antidepressants. Often habit forming.
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Cocaine
Cocaine Is reacted with NaOH to produce the free amine form known as crack.
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Caffeine
Caffeine Is a stimulant of the central nervous system. Is found in coffee beans, tea, chocolate, and soft drinks. Contains an imidazole ring.
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Nicotine
Nicotine Increases the adrenaline level in the blood. Causes addiction to tobacco. Contains a pyrrolidine ring.
N CH3
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N N
N H
Pyrimidine
(Cytosine, Thymine)
C, T