Professional Documents
Culture Documents
An Introductory Course in Organic: Dosen: Dr. Ir. Sukirno M.Eng Asisten Ariva
An Introductory Course in Organic: Dosen: Dr. Ir. Sukirno M.Eng Asisten Ariva
An Introductory Course in Organic: Dosen: Dr. Ir. Sukirno M.Eng Asisten Ariva
The original definition of "organic" chemistry came from the misconception that organic compounds were always related to life processes.
Not only organic compounds support life on Earth, but life as we know it also depends heavily on inorganic chemistry; for example, many enzymes rely on transition metals such as iron and copper; and materials such as shells, teeth and bones are part organic, part inorganic in composition
OXYGEN 65% of Body Weight is present in water and other compounds. Liquid oxygen is blue.
CARBON
18.6% of Body Weight is found in every organic molecule in the body. is ingested in food that is eaten and breathed in as a component of air. is found in the lungs as a waste product of respiration, carbon dioxide.
HYDROGEN
9.7% of Body Weight
is a component of the water molecules in the body, as well as most other compounds.
NGC 604, a region of ionized hydrogen in the Triangulum Galaxy.
NITROGEN
3.2% of Body Weight
CALCIUM
1.8% of Body Weight
is a major component of the skeletal system. is found in bones and teeth.
about one-third of the mass of human body comes from calcium, after water has been removed.
PHOSPHORUS
1.0% of Body Weight
is part of nucleic acids, energy compounds, and phosphate buffers. Red phosphorus is one of several forms taken by this element. is incorporated into the bones, combines with other elements including iron, potassium, sodium, magnesium and calcium.
is necessary for sexual function and reproduction, muscle growth, and to supply nutrients to the nerves.
POTASSIUM
0.4% of Body Weight
SODIUM
0.2% of Body Weight
CHLORINE
0.2% of Body Weight
is a part of hydrochloric acid, Is used to digest food. is involved in proper cell membrane function.
Chlorine aids in cellular absorption of water. It is the major anion in body fluids.
This is a sample of pure chlorine gas. Chlorine gas is a pale greenish yellow color.
MAGNESIUM
0.06% of Body Weight
SULFUR
0.04% of Body Weight
Percent of Mass 65 18 10
Mass (kg) 43 16 7
Nitrogen
Calcium Phosphorus Potassium Sulfur
3
1.5 1 0.25 0.25
1.8
1.0 0.780 0.140 0.140
Sodium
Chlorine Magnesium Iron Fluorine Zinc Silicon
0.15
0.15 0.05 0.006 0.0037 0.0032 0.002
0.100
0.095 0.019 0.0042 0.0026 0.0023 0.0010
Definition
Organic chemistry is a specific discipline within chemistry which involves the scientific study of the structure, properties, composition, reactions, and preparation (by synthesis or by other means) of chemical compounds consisting primarily of carbon and hydrogen, which may contain any number of other elements, including nitrogen, oxygen, halogens as well as phosphorus, silicon and sulfur.
Definition
Organic chemistry is the chemistry of the compounds of carbon, which, in combination with many other elements (in particular H, N, O, S, P and the halogens) form over 5 000 000 compounds. Many of these compounds are of immense importance.
Manufactured products
Biological matters
Sugars Proteins Fats & oils Vitamins DNA & RNA Wood Natural rubber Essential oils Natural fibres Antibiotics Fermentation products Natural flavours Natural fragrances Plant & microbial products Bio-matter
manufactured products
Imaging agents Medicines
Veterinary medicines
Disinfectants
Bio-active products
Herbicides
Antiseptics
Pesticides
Fertilizers
manufactured products
Plastics Coatings & lacquers Fibres & clothings Paper Films
Materials
Packaging
Vitamins
Foods
Dietary supplements
Flavourings
Fuels
Diesel
Peat/Turf Coal
LPG
Natural gas
in manufactured products
Lubricants Cosmetics Fragrances Pigments Dyes Inks Adhesives Explosives Detergents Surfactants Emulsifiers Coolants Photographic agents Anti-scalants Forensic chemicals Liquid crystal displays
TOP 10 REASONS
1. ORGANIC CHEMISTRY is recognised as an essential ingredient in the education of scientists in a wide range of field, particularly LIFE SCIENCES
2. ORGANIC CHEMISTRY is required for employment in the modern oil, pharmaceutical and chemical INDUSTRIES (make a major contribution to the economies of most countries) 3. To learn more about ORGANIC CHEMISTRY TECHNOLOGIES, e.g. the plastics, oil, textiles, communications, transportation, food production and processing, and drug industries. 4. ORGANIC CHEMISTRY is needed in dealing with problems of energy production, pollution, depletion of resources surround you daily 5. ORGANIC CHEMISTRY is considered to be right at the INTERFACE between the physical and biological sciences.
TOP 10 REASONS
6. To find out whats the big deal about CARBON. 7. To gain a good understanding of life AT THE MOLECULAR LEVEL (i.e. for biochemistry, microbiology, molecular biology) 8. To learn organic chemistry "for understanding" rather than just memorisation to
achieve chemistry credits.
9. To learn how living organisms are capable of doing very complex REACTIONS efficiently , in the condition of limited number of organic compounds, in the
absence of strong acids and bases, high temperatures, & nasty solvents, with only limited production of wastes.
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.
Chemical compounds
Inorganic compounds
Those were obtained from mineral deals only with simple carbon compounds, with molecular structures which do not contain carbon to carbon connections (its oxides, acids, carbonates, carbides, and minerals).
Organic compound
Those were obtained from vegetable and animal (Living Organism)
Organic chemistry received a boost when it was realized that these compounds could be treated in ways similar to inorganic compounds
It could be created in the laboratory by means other than 'vital force'.
Around 1816
Michel Chevreul started a study of soaps made from various fats and alkali.
He separated the different acids that, in combination with the alkali, produced the soap. Since these were all individual compounds, he demonstrated that
it was possible to make a chemical change in various fats, producing new compounds, without 'vital force'.
In 1828 Friedrich Whler first manufactured the organic chemical urea (carbamide), a constituent of urine, from the inorganic ammonium cyanate NH4OCN
Most people have looked to this event as the turning point to the destruction of the theory of vital force,
in 1856
A great next step was when William Henry Perkin, while trying to manufacture quinine, accidentally came to manufacture the organic dye ,
which by generating a huge amount of money greatly increased interest in organic chemistry.
in 1858 The crucial breakthrough for the theory of organic chemistry was THE CONCEPT OF CHEMICAL STRUCTURE, It was developed independently and simultaneously by Friedrich August Kekule and Archibald Scott Couper. Both men suggested that TETRAVALENT carbon atoms could link to each other to form a carbon lattice,
and that the detailed patterns of atomic bonding could be discerned by skillful interpretations of appropriate chemical reactions.
in 1874,
Another step was the laboratory preparation of DDT by Othmer Zeidler but the insecticide properties of this compound were not discovered until much later.
Oil and gas can get trapped in pockets underground such as where the rocks are folded into an umbrella shape.
http://www.worldpetroleum.org/education/ip1/ip2.html
Oil and gas can move through the porous rocks (rocks with gaps between the grains). The oil and gas move upwards from the source rock where they were formed. When they met a layer of cap rock (a rock with no spaces between the grains) the oil and gas are trapped.
38 http://www.britannica.com/eb/art/print?id=88973&articleTypeId=0
Petroleum
Oil is a complex mixture of hydrocarbons (also contains small amounts of sulfur (up to 10%), oxygen (5%), nitrogen (1%) and trace amounts of metals (V, Ni, Fe, Al, Na, Ca, Cu and U) Most hydrocarbons are saturated but up to 10% are aromatic Molecules range widely in size and are separated by boiling point (distillation tower) In addition to separation, oil refining also uses chemical reactions to enhance yields of certain components of crude oil
39
The basic refining processes take place in the crude distillation unit (CDU).
Here, crude oil is taken into the atmospheric distillation tower where it is separated into its different fractions. The hydrocarbons in crude oil have different boiling points according to the number of carbon atoms in each molecule and how they are arranged.
The oil is heated and the resultant vapors rise up the tower.
The vapors cool as they rise and condense onto trays.
http://www.doitpoms.ac.uk/tlplib/recycling-polymers/origin.php http://www.energyinst.org.uk/education/coryton/page7.htm
The lightest compounds condense at the top of the tower and are taken off as LPG
The oil then undergoes further processing prior to distribution. Sulfur is removed because when products are used the sulfur compounds emitted would smell of rotten eggs and dissolve in rain to form sulfuric acid. Other strong smelling compounds are also removed. Heavy residue is taken off at the base of the tower and reprocessed. In the fluid catalytic cracker (FCC) the heavy oil is distilled again, using a chemical catalyst this time, to produce gasoline and diesel. The heaviest sticky residue is redistilled in the vacuum distillation unit then taken to the Lubricants Zone where it is processed to make bitumen, lubricating oils and wax.
http://www.energyinst.org.uk/education/coryton/page7.htm
LPG is used for bottled gas. Gasoline is used by cars and lorries. Kerosene is used as aviation fuel and for lighting and heating. Diesel is used for road transport and trains. Lubricating oil is used for cars and machinery. Wax is used for polish, wax crayons and food packaging. Fuel oil is used by power stations, factories and ships engines. Bitumen is used for tarring roads and coating felt roofs.
http://www.energyinst.org.uk/education/coryton/page7.htm
http://www.energyinst.org.uk/education/coryton/page7.htm
Natural Gas
Can represent as large a resource as petroleum but has traditionally been a byproduct of oil exploration and fuel production
reserves better understood (gas-bearing formations) improved recovery techniques
45
Natural Gas
Advantages
Predominantly CH4 clean fuel very little processing transport via pipelines CO2 emission rate is lower than fossil fuels contributes less to photochemical smog (CH4 less reactive w.r.t. free radicals)
46
Natural Gas
Disadvantages
Storage and transport not as easy as liquid fuels (high pressures or low temperatures) CH4 produces less CO2 than other fuels but it is a potent greenhouse gas itself. (a methane molecule contributes ~20x more to the greenhouse effect than CO2)
47
Coal
Coal deposits vary in extent to which original woody plant tissue has been transformed to non-volatile (fixed) carbon.
soft coals lignite has higher water and small hydrocarbon content. 20% moisture 40% fixed carbon hard coal anthracite - 80% fixed carbon
48
The kinds of coal, in increasing order of alteration, are lignite (brown coal--immature), sub-bituminous, bituminous, and anthracite (mature). Coal starts off as peat. After a considerable amount of time, heat, and burial pressure, it is metamorphosed from peat to lignite. Lignite is considered to be "immature" coal at this stage of development because it is still somewhat light in color and it remains soft. As time passes, lignite increases in maturity by becoming darker and harder and is then classified as sub-bituminous coal. As this process of burial and alteration continues, more chemical and physical changes occur and a the coal is classified as bituminous. At this point the coal is dark and hard. Anthracite is the last of the classifications, and this terminology is used when the coal has reached ultimate maturation. Anthracite coal is very hard and shiny.
49 http://www.uky.edu/KGS/coal/coalkinds.htm
Lignite
Bituminous
Anthracite
The degree of alteration (or metamorphism) that occurs as a coal matures from peat to anthracite is referred to as the "rank" of the coal. Low-rank coals include lignite and sub-bituminous coals. These coals have a lower energy content because they have a low carbon content. They are lighter (earthier) and have higher moisture levels. As time, heat, and burial pressure all increase, the rank does as well. High-rank coals, including bituminous and anthracite coals, contain more carbon than lower-rank coals which results in a much higher energy content. They have a more vitreous (shiny) appearance and lower moisture content then lower-rank coals.
50 http://www.scsc.k12.ar.us/2000backeast/ENatHist/Members/Reynolds/Default.htm
Coal
The carbon content of coal supplies most of its heat energy per unit weight. The amount of energy in coal is expressed in British thermal units per pound. A Btu is the amount of heat needed to raise the temperature of one pound of water one degree Fahrenheit. Lignite, the youngest type of coal, has a carbon content of 25-35 percent and a heat value between 4,000 and 8,300 Btus-per-pound. It is mainly used for electric power generation. Although having a lower carbon content than bituminous coal, subbituminous coal is a desirable heat source because of its low sulfur content. Subbituminous coal has a carbon content of 35-45 percent and a heat value of 8,300 to 13,000 Btus-per-pound. This type of coal is found in the Western states and Alaska. Bituminous coal is the most abundant coal in the United States, with a large deposit found in the Allegheny Basin of the East. Bituminous coal has a carbon content of 45-86 percent with a heat value of 10,500 to 15,000 Btusper-pound. It is used primarily for generating electricity and making coke for the steel industry. Anthracite has the highest carbon content, between 86-98 percent and a heat value of nearly 1,5000 Btus-per-pound. Anthracite, found in a very small supply within the United States, is used mainly for home heating (ACF, coal). 51
Coal
Advantages
Large resource base Relatively cheap to mine and transport by rail
Disadvantages
Not as convenient as liquid fuels Emissioins particulates (PAHs) SO2 (ultimately acid rain)
52
53
http://en.wikipedia.org/wiki/Coal
54
http://www.agen.ufl.edu/~chyn/age4660/lect/lect_18/orgsstruc.gif
55
Chemical compounds
Inorganic compounds
Those were obtained from mineral
Organic compound
Those were obtained from vegetable and animal Organic compounds are always contained element carbon
carbon chemistry
What so special about carbon ?
Carbon chemistry
The number of compounds of C exceeds the number of compounds of all other elements combined. Why? 1. C can form 4 bonds in three dimensions. 2. Can bond together to form chaings, rings, spheres, sheets, tube of almost any size. 3. Forms combinations of single, double, and triple bonds. No other element can do this.
Just as there are millions of different types of living organisms on this planet, there are millions of different organic molecules, each with different chemical and physical properties. Organic compounds are always contained element carbon
The diversity of organic chemicals is due to the versatility of the carbon atom. Organic chemicals get their diversity from the many different ways carbon can bond to other atoms. The simplest organic chemicals, called hydrocarbons, contain only carbon and hydrogen atoms
#2 These C-C bonds can lead to the formation of LINEAR, BRANCHED & CYCLIC structures. #3 But wait, theres more!...In addition C can form SINGLE, DOUBLE AND TRIPLE BONDS to itself and N & O.
ISOMERS
Two Isomers have the same molecular formula but different structural formulas (and usually different properties)
Isomers of C4H10O
Relatively low factual content Understanding concepts essential Value of the subject lies in application of concepts (problem solving)
The study of science, SUCH AS Organic chemistry, is cumulative and progressive;
i.e. knowledge learned at one level (or subject) is then applied at the next level (subject).
Physical properties
CHEMICAL PROPERTIES
stability of organic chemical species neutral molecules, anions, Electronic structure cations and Relative distribution of electron in radicals) . molecule (delocalised)
Stereochemical aspects
CHEMICAL REACTIONS
Involves COVALENT BOND BREAKING AND FORMATION
Chemical Energetics . (Thermodynamics, Kinetics, Catalysis)
Solvent effects
ELECTRON FLOW
#1: REACTIONS:
A reaction will occur when there is an energetically favorable path by which electrons can flow from the electron source ("donor") to the electron acceptor ("sink")".
Obviously, you need to know the regions in molecules, which are electron rich ("nucleophilic sites") or electron poor ("electrophilic sites") to be capable of predicting the relative electronic density over a molecule.
ELECTRON FLOW
#2: Resonance;
in molecules with both p electrons in double bonds and "lone pair" electrons, electrons get "delocalised". This means they are not always localised in one place and get spread out over several atoms.
Inter- & intra-molecular forces Melting Point, Boiling Point, and solubility
Acidity & Basicity in polar and non-polar solvents
Bronsted-Lowry and Lewis acids/bases Chemical Energetics . (This subject is extremely important!) (a) Thermodynamicsenthalpy, entropy, Gibbs Free Energy equation, spontaneous reactions, exo- & endo thermic (and exo- & endogonic) reactions, position of equilibrium and Keq *Go= -RT lnKeq, Energy reaction profiles (b) Kineticsenergy of activation (*H?)/*G?, transition states, Arrhenius equation *G? = -RT lnk (where k is the rate constant a measure of relative speed of reaction) sequential reactions and rate determining step (c) Catalysisstabilisation of the transition state.
4.
5.
6.
Mathematics! Inter conversion between pH->[H+], [H+] -->pH, pKa -->Ka, & Ka --->pKa. NOTE lower "p" upper case "H or K"
POKOK BAHASAN
Topik (Before Midtest) Week Ket
Lect-1
Lect-2a Lect-2b Lect-2c Lect-2d Lect-3a Lect-3b Lect-3c
PENGENALAN SIFAT FISIKA/KIMIA DAN PENAMAAN SENYAWA ORGANIK Review Alkana (struktur, sifat fisika /kimia , reaksi pembakaran) Senyawa Hidrokarbon (penamaan, sifat fisika dan pengaruh Inter- & intra-molecular forces) sifat kimia dan pengruh dari struktur (Chemical Bonds, Drawing Electron-Dot Formulas, Formal Charges, Atomic Orbitals and the Shape of Molecules, Hybridization, 3-D dll) ALKENA DAN REAKSI ADISI ELEKTROFILIK (Alkena : struktur dan sifat fisika/kimia, Stereoisomers. E/Z. Cahn-Ingold-Prelog Rules dll
2,3
4,5
4
5
SENYAWA AROMATIK DAN REAKSI SUBSTITUSI ELEKTROFILIK Senyawa Aromatik, struktur-sifat fisika/kimia, parafinik vs aromatik, eletrofilitas
Midtest
6,7
8
Lect-3d
Week
9,10
ALKOHOL DAN REAKSI SUBSTITUSI DAN ELIMINASI NUKLEOFILIK Haloalakana dan Alkohol, struktur&sifat fisika/kimia, reaksi substitusi, nukleofilitas, reaksi
11
13
9
10 11
14 15,16, 17,18
PRESENTASI 2
Complete reaction and mechanism Effect of strucure, solvent, temperature, pressure, catalyst etc.
Penilaian
Quis 15% Home work 10% Presentation 25% Midtest 25% Final Test 25%