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Organic Chemistry
WHY YOU SHOULD STUDY
ORGANIC CHEMISTRY?
You are a future chemical engineer.
You will work in the field of industry
Why
The building of very complex organic compound architecture by
appropriate choice of sequential combination of reaction
provide synthesis method that as describe as elegant and beautiful
So the unique work of art can only be appreciated by those who know
organic reaction and have try to design simple synthesis by themselves
As people said, only one who play chess can feel the pleasure following a
game between the grandmasters
TOP 10 REASONS
6. To find out whats the big deal about CARBON.
10. To find out how the spatial arrangements of those little ELECTRON clouds
can ultimately determine the structure, reactivity that in turn controls the
function of both small and huge organic molecules.
When you learn organic chemistry
Then you had better know its characteristic
Example : football
To many people,
organic means natural.
In chemistry
organic means carbon-based.
To a chemist,
Firstly, they learned how to turn plant and animal compounds into
all kinds of other things
Around 1816
Michel Chevreul started a study of SOAPS made
from various FATS and alkali.
He separated the different acids from the fats, then
He combined them with the alkali to produced the
soaps.
Soap still has something in common with fat (plant and animal
matter.
their molecules were still made of carbon atoms.
in 1856
A great next step was when William Henry Perkin, while
trying to manufacture quinine, accidentally came to
manufacture the ORGANIC DYE
Carbon therefore forms four bonds with other atoms by sharing electron,
(each bond consisting of 1 e of carbon + 1e of other atom).
Alkanes are the first class of simple hydrocarbons and contain only
carbon-carbon single bonds.
C6H14
50
HYDROCARBONS
Alkane: single bonds, sp3 carbons
Cycloalkane: carbons form a ring
Alkene: double bond, sp2 carbons
Cycloalkene: double bond in ring
Alkyne: triple bond, sp carbons
Aromatic: contains a benzene ring
51
COMPOUNDS CONTAINING OXYGEN
Alcohol: R-OH
Ether: R-O-R'
O
Aldehyde: RCHO
CH3CH2 C H
O
Ketone: RCOR'
CH3 C CH3
52
CYCLIC ETHERS AND
KETONES
O
O
THF
(tetrahydrofuran) cyclopentanone
53
CARBOXYLIC ACIDS
AND THEIR DERIVATIVES
Carboxylic Acid: RCOOH O
Ester: RCOOR'
O
Amide: RCONH2 C Cl
O O
C NH C OCH3
2
=>
54
CYCLIC ESTERS
O O
O O
55
COMPOUNDS CONTAINING NITROGEN
O
CH3 C N
N CH3
=>
56
What ASPECTS OF ORGANIC MOLECULES
are we going to study ?
NAMING OF OC
IUPAC rules
PHYSICAL PROPERTIES
Basic Structure
CHEMICAL PROPERTIES
Electronic Structure
CHEMICAL REACTIONS
Mechanism
NAMING ORGANIC MOLECULES
Note :
Sometimes compounds have several different names.
the IUPAC name may not be the one most commonly used.
they may be the names invented for compounds because of their origin
or name were attempted by a nomenclature system before the IUPAC
system .
The two basic features of the IUPAC name.
The element C and H, do not appear directly in the compound names, instead the
IUPAC system names a compound based on the number of carbon atoms linked
together in the longest continuous chain of carbon atoms.
Compounds may have the same atoms and bond connectivity but
differ in the spatial arrangement of the atoms, such that the two
arrangements cannot be interconverted at room temperature.
These are called stereoisomers.
Example :
The rigid structure (prohibits free rotation of the atoms)
of a ring, even though it is made up of single bond
In this approach, the two groups on each end of the double bond is
prioritized according to a set of arbitrary rules( Cahn-Ingold-Prelog
rules, and then names the stereomers according to the orientation
of the two highest priority groups.
PHYSICAL PROPERTIES
PhASEs : Gas, LIQUID , Solid
melting/boiling points, Inter molecular forces
solubilities in various solvents, Interaction
Polarity dielectric constants,
spectral data)
CHEMICAL REACTIVITY
Stereochemical aspects
Formal charge
Covalent Bond Breaking
+ _
A B A B
Arrhenius definition:
Acids dissociate in water releasing H3O+ ions; bases dissociate in water releasing OH ions.
Brnsted-Lowry definition:
Acids are proton (H+) donors, bases are proton acceptors;
ACID-BASE REACTIONS
an electron donor
(a Lewis base) Electron acceptor
(a Lewis acid)
nucleophile electrophile
Lewis definition:
Acids are electron-pair acceptors, bases are electron-
pair donors;
69
PSECIES PRODUCED BY BOND BREAKING
electrophile nucleophile
-OH
H+
Br+ :NH3
H H
C C
H H
ELECTROPHILES NUCLEOPHILES:
71
Active species
1. NUCLEOPHILES (nucleus loving)
Electron-rich reagent that forms a bond by donating an
e- pair to an e- poor site
3. RADICALS
Species with an unpaired electron. The unpaired
electrons cause radicals to be highly chemically reactive.
Homolytic bond breaking
(radical reactions)
RADICAL (CHEMISTRY)
a single molecule breaks apart into two free radicals in thermal cracking
process which operated at (400C - 460 C)
Types of reactions
ADDITION, Chemical Energetics .
(saturation, polimerization) (Thermodynamics,
Kinetics, Catalysis)
ELIMINATION
(dehydration, dehalogenation)
SUBSTITUTION, Solvent effects
(alkylation, esterification, tranesterifcation
REARRANGEMENT
isomerization
TYPES OF ORGANIC REACTIONS
1. ADDITION REACTIONS
two reactants add to form one product
H H Br H
C C + HBr H C C H
H H H H
2. ELIMINATION REACTIONS
one reactant splits apart into two products
H Br H H
NaOH + HBr
H C C H C C
H H H H
H H
hv
H C H Cl Cl H C Cl H Cl
H H
4. REARRANGEMENT REACTIONS
One reactant rearranges its bonds to
yield a different product
CH3CH2 H CH3 H
acid
C C C C
H H H CH3
2. Inter- & intra-molecular forces Melting Point, Boiling Point, and solubility
GROUP ASSIGNMENT
2 NAMING ORGANIC COMPOUNDS: 1,2
Straight chain (alkanes, alkenes, alkynes) and ring chain hydrocarbon : rootname, numbering locant, complex substituent, prioritization of double bond,
Halogen, oxygen, nitrogen containing compound : rootname pattern (prefix, suffix), prioritization of functional group, numbering locant
STEREO ASPECT OF HYDROCARBON AND NAMING E/Z , R/S
Structural isomer, Conformer (Rotation around single bond ), Newman Projection,
Stereoisomer (Rigid structure of double bond ) Cis/trans and E/Z structure designation , Cahn-Ingold-Prelog Rules, Enantiomer and R/S structure designation), 3-D drawing
MID TEST 7
Topic (AFTER MiDtest) Wee Ket
k
MIDTEST 7
REACTANT PRODUCT
Naming
Naming Usage :
Physical properties Physical properties
Chemical reactivity Chemical reactivity
Mechanical properties
Chemical structure Electrical properties
Comparison to other similar Etc.
compound
PRESENTATION OF ORGANIC CHEMICALS
INTRO
Product name, functional group classification
Product usage
Product special characteristic (Physical/ chemical/ mechanical
properties) that support its function
MAIN POINTS
Explanation of the reason for having such special
characteristic
3D Structure
Non kovalen interaction
elektronik distribution etc.
CLOSING
EVALUATION
Quis +HW 25%
Report Presentation 25%
Midtest 25%
Final Test 25%
Different Types of Chemistry
Organic chemistry
Organic chemistry
Organic
Chemicals
LPG Peat/Turf
Fuels
Petrol
Coal
Diesel
manufactured products
Fibre
Fats & Oils
Vitamins
Sugars
Foods
Flavourings
Dietary supplements
Anti-oxidants
Colourants
manufactured products
Plastics
Coatings & lacquers
Fibres & clothings
Paper
Films Materials
Packaging
Wound dressings
Medical implants
manufactured products
Lubricants Detergents
Cosmetics Surfactants
Fragrances Emulsifiers
Pigments Coolants
Dyes Photographic agents
Inks Anti-scalants
Adhesives Forensic chemicals
Explosives Liquid crystal displays
manufactured products
Imaging agents
Medicines Veterinary medicines
Fertilizers Fungicides