PENGANTAR KIM ORG Biologi 2010 Universitas Airlangga | Bio… Life !!! ……….. Himbio… Jaya !!! pengantar kim org1
Senyawa organik, struktur dan reaksi
organik
07/28/2018
1
What is Organic Chemistry?
It is defined as the study of hydrocarbons (compounds of
hydrogen and carbon) and their derivatives
Organic chemistry = Chemistry of carbon-based molecules
Organic molecules = Carbon-based molecules
30 million Organic Compounds
1.5 million Inorganic Compounds, 95%
Containing Carbon atom
Animal and plant matter, Foods, Pharmaceuticals, Cosmetics,
Fertilizers, Plastics, Petrochemicals, Clothing
Why Carbon
Why is it the element of life on earth?
• Has Four Bonding Electrons
• Unique Strong Covalent Bonds
• Strong Single, Double and Triple Bonds
Average Bond Energies (KJ mol-1)
C-C607
Si-Si
C-N754 Si-N
230 C-H416 Si-H
470 C-O
336 Si-O
323
368
O-Si-O = Sand and Rocks
N-N
163 dan O-O 157
• Carbon: unique in its ability to catenate
[can form chains of atoms]
• Forms molecules composed of C-C bonds
Some properties of organic molecules
Stability: composed of stable C-C covalent bonds
• Defined molecular structures
• Defined three-dimensional shapes
C
C
C
C
C
C
Linear molecules
07/28/2018
C
C
C
C
C
C
C
C
Branched molecules
C
C
C
C C
Cyclic molecules
4
Organic chemicals are universal
Biological matter
• Plants
• Animals
• Microbes
Geological matter
• Fossil Fuels
• Other
Organic
Chemicals
Manufactured
products
07/28/2018
Atmospheric
and
cosmic matter
5
Biological organic chemicals
Sugars
Proteins
Fats & oils
Vitamins
DNA & RNA
Wood
Natural
rubber
Essential oils
07/28/2018
Natural fibres
Antibiotics
Fermentation
products
Natural
flavours
Natural
fragrances
Plant &
microbial
products
6
Organic chemicals in manufactured
products
Veterinary medicines
Medical imaging agents
Medicines
Disinfectants
Bio-active
products
Antiseptics
Herbicides
Pesticides
Fertilizers
Fungicides
Plant growth
hormones
07/28/2018
7
Organic chemicals in manufactured
products
Plastics
Coatings & lacquers
Fibres & clothings
Paper
Films
Materials
Packaging
Wound dressings
Medical implants
07/28/2018
8
Organic chemicals in manufactured
products
Fibre
Fats & Oils
Vitamins
Sugars
Foods
Flavourings
Dietary supplements
Anti-oxidants
Colourants
Methanol/Ethanol
“Petrol”
“Diesel”
Fuels
Peat/Turf
Coal
LPG
Natural gas
07/28/2018
9
Organic chemicals in manufactured
products
Miscellaneous
Detergents
Lubricants
Surfactants
Cosmetics
Emulsifiers
Fragrances
Coolants
Pigments
Photographic
Dyes
agents
Anti-scalants
Inks
Forensic
Adhesives
chemicals
Liquid
Explosives
crystal displays
07/28/2018
10
Simplest Organic molecule
Carbon has 4 valence electrons
H
H
H C H
H C H
H
H
methane
H
Ne
Neon
C
Stable Octet required
Covalent Bonding – Atoms Share Electrons
Covalent bonding
CCl4 - Covalent HCl - Covalent
Cl
Cl C Cl
Cl
H Cl
NH3 - Covalent
H N H
H2O - Covalent
H O H
07/28/2018
MgF2 - Ionic
[Mg]2+ [
F
]2–
NaCl - Ionic
[Na] + [ Cl ]–
H
H2 - Covalent
OH– - Covalent
H H
O H
For more lessons,
12 visit
www.chalkbored.com
C(6) - 1s2, 2s2, 2px1, 2py1, 2pz0
lowest energy
state
2
1
1
C(6) - 1s , 2s , 2px ,
Excited state
+
2s
4 sp3
1
2pz
Hybridization
+
+
2py
1
2py ,
2px
2pz
4 X sp3
Methane is Tetrahedral
0
109.5
H
C H
H
H
Sp3 hybridized carbon
4 equivalent C-H bonds (s-bonds)
All purely single bonds are called s-bonds
Electrophile dan Nucleophile?
Electrophile “electron lover” abbreviated
E+ species that is attracted toward a
negative center. Electrophile is Lewis
acid, H+, ZnCl2, AlCl3
Nucleophile “nucleus lover” abbreviated
Nu:- species that is attracted to positive
center
07/28/2018
15
Nucleophilicity and Basicity
Nucleophilicity is a measure of reagent’s ability
to cause a substitution reaction
H2O ROH Cl- Br - -OH -OR I- - CN
Increasing Nu: right
HO- + CH3CH2-Br
CH3CH2OH + Br –
OH- acting as Nu:
07/28/2018
16
Basicity is a measure a reagent’s ability to accept
a proton in acid base reaction
I- Br - Cl- ROH H2O
CN
-
-
OH
OR
-
Increasing basicity: right
HO- + H-Cl
H2O + Cl
CH3CH-CH2 + -OH
07/28/2018
CH3CH=CH2
Br H
17
Electrophilic Aromatic Substitution
(Bromination of Toluene)
Background
Nucleophile
an
Electrophile
07/28/2018
- A Lewis Base with a pair of unshared
electrons that seeks a positive part of
atom.
- A Lewis Acid seeking an electron pair
18
Leaving group?
Gugus pergi/gugus lepas in term substitution
reaction
Halida ions are good leaving group because
they are very weak bases
Increase reactivity RF RCl RBr RI
F- is strong base than the other halida, poor
leaving group
OH poor leaving group,
07/28/2018
19
07/28/2018
20
Hyperconjugation
Electrons in neighboring filled orbital stabilize vacant
antibonding orbital – net positive interaction
Alkyl groups are better than H
07/28/2018
21
Rotation of Bond Is
Prohibitive
This prevents rotation about a carbon-carbon
double bond (unlike a carbon-carbon single bond).
Creates possible alternative structures
07/28/2018
22
Fractional distillation of crude oil
Natural Gas (C1-C4)
Gasoline (C4-C12)
Bpt (40-200 ºC)
Petroleum
Kerosene (C12-C16)
Bpt (200-250 ºC)
Heating oil (C15-C18)
Bpt (250-300 ºC)
Straight-chain alkanes are a pure fuel, because of engine knock.
n-Heptane has an octane rating = 0
Catalytic cracking
2,2,4-trimethylpentane has an octane rating = 100
Late 18th century:
• Compounds from living organisms - Organic
• Compounds from lifeless matter – Inorganic
• Organic compounds thought to have ‘vital force’
Wöhler 1828
Ammonium cyanate
D
Urea
(Heat)
• Discredited concept of ‘vital force’
07/28/2018
24
• Lactic acid composed of Carbon, Hydrogen and Oxygen
• Fixed proportion: 1C:2H:1O
• Empirical formula: CH2O
• Majority of ‘organic’ substances and many ‘inorganic’
composed of Carbon, Hydrogen and maybe other elements
• Mid 19th Century: re-define organic substances
• Those composed of Carbon, Hydrogen (usually) and other
elements (maybe)
• 1850-1860: Concept of Molecules
• Atoms of Carbon and other elements connected by covalent
bonds
• Hence, fixed proportions of elements
07/28/2018
25
organik
07/28/2018
1
What is Organic Chemistry?
It is defined as the study of hydrocarbons (compounds of
hydrogen and carbon) and their derivatives
Organic chemistry = Chemistry of carbon-based molecules
Organic molecules = Carbon-based molecules
30 million Organic Compounds
1.5 million Inorganic Compounds, 95%
Containing Carbon atom
Animal and plant matter, Foods, Pharmaceuticals, Cosmetics,
Fertilizers, Plastics, Petrochemicals, Clothing
Why Carbon
Why is it the element of life on earth?
• Has Four Bonding Electrons
• Unique Strong Covalent Bonds
• Strong Single, Double and Triple Bonds
Average Bond Energies (KJ mol-1)
C-C607
Si-Si
C-N754 Si-N
230 C-H416 Si-H
470 C-O
336 Si-O
323
368
O-Si-O = Sand and Rocks
N-N
163 dan O-O 157
• Carbon: unique in its ability to catenate
[can form chains of atoms]
• Forms molecules composed of C-C bonds
Some properties of organic molecules
Stability: composed of stable C-C covalent bonds
• Defined molecular structures
• Defined three-dimensional shapes
C
C
C
C
C
C
Linear molecules
07/28/2018
C
C
C
C
C
C
C
C
Branched molecules
C
C
C
C C
Cyclic molecules
4
Organic chemicals are universal
Biological matter
• Plants
• Animals
• Microbes
Geological matter
• Fossil Fuels
• Other
Organic
Chemicals
Manufactured
products
07/28/2018
Atmospheric
and
cosmic matter
5
Biological organic chemicals
Sugars
Proteins
Fats & oils
Vitamins
DNA & RNA
Wood
Natural
rubber
Essential oils
07/28/2018
Natural fibres
Antibiotics
Fermentation
products
Natural
flavours
Natural
fragrances
Plant &
microbial
products
6
Organic chemicals in manufactured
products
Veterinary medicines
Medical imaging agents
Medicines
Disinfectants
Bio-active
products
Antiseptics
Herbicides
Pesticides
Fertilizers
Fungicides
Plant growth
hormones
07/28/2018
7
Organic chemicals in manufactured
products
Plastics
Coatings & lacquers
Fibres & clothings
Paper
Films
Materials
Packaging
Wound dressings
Medical implants
07/28/2018
8
Organic chemicals in manufactured
products
Fibre
Fats & Oils
Vitamins
Sugars
Foods
Flavourings
Dietary supplements
Anti-oxidants
Colourants
Methanol/Ethanol
“Petrol”
“Diesel”
Fuels
Peat/Turf
Coal
LPG
Natural gas
07/28/2018
9
Organic chemicals in manufactured
products
Miscellaneous
Detergents
Lubricants
Surfactants
Cosmetics
Emulsifiers
Fragrances
Coolants
Pigments
Photographic
Dyes
agents
Anti-scalants
Inks
Forensic
Adhesives
chemicals
Liquid
Explosives
crystal displays
07/28/2018
10
Simplest Organic molecule
Carbon has 4 valence electrons
H
H
H C H
H C H
H
H
methane
H
Ne
Neon
C
Stable Octet required
Covalent Bonding – Atoms Share Electrons
Covalent bonding
CCl4 - Covalent HCl - Covalent
Cl
Cl C Cl
Cl
H Cl
NH3 - Covalent
H N H
H2O - Covalent
H O H
07/28/2018
MgF2 - Ionic
[Mg]2+ [
F
]2–
NaCl - Ionic
[Na] + [ Cl ]–
H
H2 - Covalent
OH– - Covalent
H H
O H
For more lessons,
12 visit
www.chalkbored.com
C(6) - 1s2, 2s2, 2px1, 2py1, 2pz0
lowest energy
state
2
1
1
C(6) - 1s , 2s , 2px ,
Excited state
+
2s
4 sp3
1
2pz
Hybridization
+
+
2py
1
2py ,
2px
2pz
4 X sp3
Methane is Tetrahedral
0
109.5
H
C H
H
H
Sp3 hybridized carbon
4 equivalent C-H bonds (s-bonds)
All purely single bonds are called s-bonds
Electrophile dan Nucleophile?
Electrophile “electron lover” abbreviated
E+ species that is attracted toward a
negative center. Electrophile is Lewis
acid, H+, ZnCl2, AlCl3
Nucleophile “nucleus lover” abbreviated
Nu:- species that is attracted to positive
center
07/28/2018
15
Nucleophilicity and Basicity
Nucleophilicity is a measure of reagent’s ability
to cause a substitution reaction
H2O ROH Cl- Br - -OH -OR I- - CN
Increasing Nu: right
HO- + CH3CH2-Br
CH3CH2OH + Br –
OH- acting as Nu:
07/28/2018
16
Basicity is a measure a reagent’s ability to accept
a proton in acid base reaction
I- Br - Cl- ROH H2O
CN
-
-
OH
OR
-
Increasing basicity: right
HO- + H-Cl
H2O + Cl
CH3CH-CH2 + -OH
07/28/2018
CH3CH=CH2
Br H
17
Electrophilic Aromatic Substitution
(Bromination of Toluene)
Background
Nucleophile
an
Electrophile
07/28/2018
- A Lewis Base with a pair of unshared
electrons that seeks a positive part of
atom.
- A Lewis Acid seeking an electron pair
18
Leaving group?
Gugus pergi/gugus lepas in term substitution
reaction
Halida ions are good leaving group because
they are very weak bases
Increase reactivity RF RCl RBr RI
F- is strong base than the other halida, poor
leaving group
OH poor leaving group,
07/28/2018
19
07/28/2018
20
Hyperconjugation
Electrons in neighboring filled orbital stabilize vacant
antibonding orbital – net positive interaction
Alkyl groups are better than H
07/28/2018
21
Rotation of Bond Is
Prohibitive
This prevents rotation about a carbon-carbon
double bond (unlike a carbon-carbon single bond).
Creates possible alternative structures
07/28/2018
22
Fractional distillation of crude oil
Natural Gas (C1-C4)
Gasoline (C4-C12)
Bpt (40-200 ºC)
Petroleum
Kerosene (C12-C16)
Bpt (200-250 ºC)
Heating oil (C15-C18)
Bpt (250-300 ºC)
Straight-chain alkanes are a pure fuel, because of engine knock.
n-Heptane has an octane rating = 0
Catalytic cracking
2,2,4-trimethylpentane has an octane rating = 100
Late 18th century:
• Compounds from living organisms - Organic
• Compounds from lifeless matter – Inorganic
• Organic compounds thought to have ‘vital force’
Wöhler 1828
Ammonium cyanate
D
Urea
(Heat)
• Discredited concept of ‘vital force’
07/28/2018
24
• Lactic acid composed of Carbon, Hydrogen and Oxygen
• Fixed proportion: 1C:2H:1O
• Empirical formula: CH2O
• Majority of ‘organic’ substances and many ‘inorganic’
composed of Carbon, Hydrogen and maybe other elements
• Mid 19th Century: re-define organic substances
• Those composed of Carbon, Hydrogen (usually) and other
elements (maybe)
• 1850-1860: Concept of Molecules
• Atoms of Carbon and other elements connected by covalent
bonds
• Hence, fixed proportions of elements
07/28/2018
25