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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.
When you learn something Then you had better know its characteristic
In the United States the word football refers to a game played with an oval-shaped ball that players pass with their hands or hold with their hands while they run with it. In England football refers to a game played with a round ball that players kick with their feet. (In the United States people call this game soccer.)
A word that means one thing to one person might mean something completely different to another person.
something natural like compost is organic fertilizer, . while human-made or synthetic fertilizers are not organic
In chemistry organic means carbon-based. To a chemist, an OC is any compound that contains carbon. That is, an organic compound is any compound whose molecules contain carbon atoms.
How in the world did this happen? Why do chemists use the word organic so differently from everyone else?
A long time ago the word organic was used to describe anything that came from an organismanything that came from a living thing.
Chemists who worked with substances found in living things were called organic chemists.
CHEMICAL COMPOUNDS
Inorganic compounds
Those were obtained from mineral such as oxides, acids, carbonates, carbides
(simple carbon compounds, with molecular structures which do not contain carbon to carbon connections )
Organic compound
Those were obtained from vegetable and animal (Living Organism)
At that time, they preferred to direct their investigations toward inorganic materials that seemed more easily studied and more promising.
What organic chemists did, at that time? 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. These works demonstrated that it was possible to make a chemical change in various fats, producing new compounds, without 'vital force'.
Soap still has something in common with plant and animal matter: their molecules were still made of carbon atoms.
So all the chemist are doing is taking apart its molecules and putting the atoms back together in different ways Or turn one substance into another
Organic chemists also figured out how to synthesize an animal compounds from nonliving materials. In 1827 a chemist named Friedrich Whler was playing with some mineral salts. He accidentally made urea, a compound found in urine
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
a colored substance that has affinity to the substrate to which it is being applied
This works beside generating a huge amount of money, it greatly increased interest in organic chemistry.
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.
There was more to come. Petroleum is mostly carbon. Scientists learned how to make all kinds of other plant and animal compounds from it. For example, they made vitamins and sugars from petroleum. Organic chemists branched out even further. They started making new carbon-based materials from nonliving things. They made everything from gasoline to plastics out of petroleum
organic chemistry grew to be the chemistry of all carbon compounds, whether or not they came from living things. Petroleum, gasoline, and plastics are all carbon-based, and so they came to be considered organic by chemists.
TOTAL SYNTHESIS OF COMPLEX NATURAL COMPOUNDS started with urea, increased in complexity to glucose and terpineol, and in 1907,
synthesis of complex human hormones and their modified derivatives, for example cholesterol-related compounds that benefits pharmaceutical industries.
So when we talk about organic chemists, were not talking about chemists who only use all-natural substances. Were talking about chemists who make and study compounds that are made of carbon, whether the compounds are natural or synthetic.
So here we are today, with the word organic meaning carbon-based to chemists. Theres a real reason for chemists to have their own meaning for the word organic, and it has to do with a concern in chemistry for how substances behave. A substance behaves or reacts the way it does because of the atoms its molecules are made of, and how they are put together. This means carbon-based compounds should behave differently from compounds based on other elements. Therefore, it is useful for chemists to group carbon-based compounds together because they are similar in a chemically interesting way.
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 million compounds.
The simplest organic chemicals, called hydrocarbons, contain only carbon and hydrogen atoms
An organic compound is any member of a large class of chemical compounds whose molecules contain carbon; (for historical reasons discussed below, a few types of compounds such as carbonates, carbon oxides and cyanides, as well as elemental carbon are considered inorganic.
Inorganic Compounds: NaCl - sodium chloride CO2 - carbon dioxide H2O - water NO2 - nitrogen dioxide HCl - hydrochloric acid CuCl2 - copper(II) chloride Fe2O3 - iron(III) oxide MgCl2 - magnesium chloride
Organic molecules contain both carbon and hydrogen. Though many organic chemicals also contain other elements, it is the carbonhydrogen bond that defines them as organic.
Organic chemistry defines life. There are organic chemicals that make up your hair, your skin, your fingernails, and so on.
The diversity of organic chemicals is due to the versatility of the carbon atom. Why is carbon such a special element? Let's look at its chemistry in a little more detail.
Carbon (C) appears in the second row of the periodic table and has four bonding electrons in its valence shell . Similar to other non-metals, carbon needs eight electrons to satisfy its valence shell. Carbon therefore forms four bonds with other atoms (each bond consisting of one of carbon's electrons + one electrons of other atom). Every valence electron participates in bonding, thus a carbon atom's bonds will be distributed evenly over the atom's surface. These bonds form a tetrahedron (a pyramid with a spike at the top), as illustrated below:
The simplest organic chemicals, called hydrocarbons, contain only carbon and hydrogen atoms; the simplest hydrocarbon (called methane) contains a single carbon atom bonded to four hydrogen atoms
But carbon can bond to other carbon atoms in addition to hydrogen, as illustrated in the molecule ethane
But carbon can bond to other carbon atoms in addition to hydrogen, as illustrated in the molecule ethane
In fact, the uniqueness of carbon comes from the fact that it can bond to itself in many different ways. Carbon atoms can form long chains branched chains:
neighboring carbon atoms can form double and triple bonds in addition to single carbon-carbon bonds
There appears to be almost no limit to the number of different structures that carbon can form.
Keep in mind that each carbon atom forms four bonds. As the number of bonds between any two carbon atoms increases, the number of hydrogen atoms in the molecule decreases
Can bond together to form chains, rings, spheres, sheets, tube of almost any size.
3. C can form SINGLE, DOUBLE AND TRIPLE BONDS to itself and N & O.
hydrocarbons
The simple hydrocarbons come in three varieties depending on the type of carbon-carbon bonds that occur in the molecule Alkanes are the first class of simple hydrocarbons and contain only carbon-carbon single bonds. The alkanes are named by combining a prefix that describes the number of carbon atoms in the molecule with the root ending "ane".
The chemical formula for any alkane is given by the expression CnH2n+2
The names and prefixes for the first ten alkanes are given in the following table.
Carbon Alkane Prefix Atoms Name 1 2 3 4 5 6 7 8 9 10 Meth Eth Prop But Pent Hex Hept Oct Non Dec Methane Ethane Propane Butane Pentane Hexane Heptane Octane Nonane Decane Chemical Structural Formula Formula CH 4 C2H6 C3H8 C4H10 C5H12 C6H14 C7H16 C8H18 C9H20 C10H22 CH4 CH3CH3 CH3CH2CH3 CH3CH2CH2CH3 CH3CH2CH2CH2CH3 ...
The second class of simple hydrocarbons, the alkenes, consists of molecules that contain at least one double-bonded carbon pair. Alkenes follow the same naming convention used for alkanes. A prefix (to describe the number of carbon atoms) is combined with the ending "ene" to denote an alkene. Ethene, for example is the two- carbon molecule that contains one double bond. The chemical formula for the simple alkenes follows the expression CnH2n. Because one of the carbon pairs is double bonded, simple alkenes have two fewer hydrogen atoms than alkanes.
Alkynes are the third class of simple hydrocarbons and are molecules that contain at least one triple-bonded carbon pair. Like the alkanes and alkenes, alkynes are named by combining a prefix with the ending "yne" to denote the triple bond. The chemical formula for the simple alkynes follows the expression CnH2n-2.
Isomers
Because carbon can bond in so many different ways, a single molecule can have different bonding configurations. C6H14
Both molecules have identical chemical formulas however, their structural formulas (and thus some chemical properties) are different
FUNCTIONAL GROUPS.
hydrocarbons can also contain other elements. In fact, many common groups of atoms can occur within organic molecules, these groups of atoms are called functional groups. One good example is the hydroxyl functional group. The hydroxyl group consists of a single oxygen atom bound to a single hydrogen atom (-OH). The group of hydrocarbons that contain a hydroxyl functional group is called alcohols
Functional Groups
There are a wide variety of functional groups that you should recognize
The FG affect the reactions, structure, and physical properties of every compound in which they occur It will be easier to recognize them, as we learn about them in each chapter
FUNCTIONAL GROUPS
FG is a collection of atoms at a site within a molecule with a common bonding pattern The group reacts in a typical way, generally independent of the rest of the molecule
For example, the double bonds in simple and complex alkenes react with bromine in the same way
bonds that are represented as alternating single and double C-C bonds in a six-membered ring
Alkenes have a C-C double bond Alkynes have a C-C triple bond
FUNCTIONAL GROUPS WITH CARBON SINGLY BONDED TO AN ELECTRONEGATIVE ATOM Alkyl halide: C bonded to halogen (C-X) Alcohol : C bonded O of a hydroxyl group (C OH) Ether : Two Cs bonded to the same O (C O C) Amine : C bonded to N (C N) Thiol : C bonded to SH group (C SH) Sulfide : Two Cs bonded to same S (C S C)
Bonds are polar,
with partial positive charge on C (+) and partial negative charge () on electronegative atom
Aldehyde: one hydrogen bonded to C=O Ketone : two Cs bonded to the C=O Carboxylic acid: OH bonded to the C=O Ester : C-O bonded to the C=O Amide : C-N bonded to the C=O Acid chloride: Cl bonded to the C=O
Carbonyl C has partial positive charge (+) Carbonyl O has partial negative charge (-).
49
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
50
O CH3CH2 C H
O CH3 C CH3
51
52
O C OH
O C Cl
O C OCH3
=>
CYCLIC ESTERS
O O
O O
Cyclic ester
54
O N CH3
CH3
C N
=>
55
NAMING
To be able to name such vast numbers of possible molecules requires a systematic approach consisting of a set of arbitrary rules which are readily learned and applied to each molecule individually to generate the name. It called IUPAC nomenclature system. Note that in addition to names invented for compounds because of their origin, there were other attempts to produce a systematic nomenclature system before the IUPAC system . Therefore, sometimes compounds have several different names, of which the IUPAC name may not be the one most commonly used.
the number of carbon atoms in the longest continuous chain of carbon atoms containing the functional group
Example : The rigid structure (prohibits free rotation of the atoms) of a ring, even though it is made up of single bond The rigid structure of a double bond
PHYSICAL PROPERTIES
phASEs : Gas, LIQUID , Solid melting/boiling points, solubilities in various solvents, Polarity dielectric constants, spectral data) Inter molecular forces Interaction
stability of chemical species (neutral atoms/molecules, anions, cations and radicals, acidity/basicity etc
Electronic structure Relative distribution of electron in molecule (delocalised), resonance Stereochemical aspects
Solvent effects
ORGANIC REACTION
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.
The most probable product (major product) of a reaction results from the best electron source attacking the best electron sink.
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"
Before Midtest)
1 INTRODUCTION :
Reason to study and characteristic of organic chemistry, history highlight of organic compound, Hydrocarbon , Functional group , Family of organic compound, aspect in organic molecule (naming, physical , chemical reactivity, chemical reactions)
Week
1
Ket
1,2
4 REACTION OF HIDROCARBON
Reactivity of alkane : stable sigma bond (low energy level)
2,3
FREE RADICAL REACTION (HALOGENATION AND CRACKING ADDITION REACTION OF DOUBLE BOND (ALKENES)
Chemical reactivity of double bond of alkene : pi bond (higher energi level, electron rich site) Electrofilic addition mechanism : acid catalysis, carbocation, Markovnikov rules, carbocation stability and rearrangement , and antiMarkovnikov rules, Addition Polymerization of alkene : Cationic and Free Radical mechanisme
PRESENTASI TOPIC 1 CRACKING REACTION PRESENTASI TOPIC 2 ADDITION REACTION OF DOUBLE BOND PRESENTASI TOPIC 3 SUBSTITUTION REACTION OF AROMATIC COMPOUND MID TEST
4 5, 6 7
Wee k
7 1
Ket
MIDTEST
SUBSTITUTION AND ELIMINATION REACTION OF HALOALKANES/ALCOHOL Reactivity of haloalkane and alcohol group, Nucleofilic substition mechanism : SN2, SN1, E1,E2 Influenced of reactant structure, nucleophility, solvent, temperature on SN1, SN2 an E1 and E2 SUBSTITUTION AND ELIMINATION REACTION OF CARBOXYL GROUP Reactivity of carboxyl group Nucleofilic substition mechanism : acid catalysis Esterification, PRESENTATION TOPIC IV Substitution Reaction (Haloalkanes, Alcohols) Reaction PRESENTATION TOPIC V Elimination Reaction (Haloalkane, Alcohol)reaction
3 4
5
6 7
We are going to learn organic chemistry through naming, identifying physical/chemical properties, and describing reaction mechanism of ORGANIC CHEMICALS especially the MANUFACTURED PRODUCT
manufactured products
Natural gas Methanol/Ethanol
LPG
Peat/Turf
Fuels
Petrol
Diesel
Coal
manufactured products
Fats & Oils Sugars
Fibre
Vitamins
Foods
Dietary supplements
Flavourings
Colourants
Anti-oxidants
manufactured products
Plastics Coatings & lacquers Fibres & clothings Paper Films
Materials
Packaging
manufactured products
Lubricants Cosmetics Fragrances Pigments Dyes Inks Adhesives Explosives Detergents Surfactants Emulsifiers Coolants Photographic agents Anti-scalants Forensic chemicals Liquid crystal displays
manufactured products
Imaging agents Medicines
Veterinary medicines
Disinfectants
Bio-active products
Herbicides
Antiseptics
Pesticides
Fertilizers
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
MAIN POINTS Explanation of the reason for having such special characteristic
3D Strukture Non kovalen interaction elektronik distribution etc.
Gasoline is a complex mixture of over 500 hydrocarbons that may have between 5 to 12 carbons. Smaller amounts of alkane cyclic and aromatic compounds are present. It is most often produced by the fractional distillation of crude oil
Straight-run gasoline (directly from the refinery distillation column) has an octane number of about 70. In other words, straight-run gasoline has the same knocking properties as a mixture of 70% isooctane and 30% heptane.
If fuel octane is too low for a given compression ratio, the fuel prematurely ignites too early and the fuel charge EXPLODES rather than BURNS resulting in incomplete combustion. The net effect is a loss in power, possible engine damage, and an audible "knock" or "ping", referred to as detonation. The octane number is determined by comparing the characteristics of a gasoline to isooctane (2,2,4-trimethylpentane) and heptane. Isooctane is assigned an octane number of 100. It is a highly branched compound that burns smoothly, with little knock.
On the other hand, heptane, a straight chain, unbranched molecule is given an octane rating of zero because of its bad knocking propertie
EVALUATION
Quis +HW 25% Report Presentation 25% Midtest 25% Final Test 25%