chapter 1 - part 1 introduction to organic chemistry

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Mohd Zulkhairi Abdul Rahim Email: mohd.zulkhairi@unikl.edu.myExt: 2090 H/P: 013-6779113Office: Lab InstrumentationCLB10803Analytical & Organic Chemistry

CHAPTER 1 : INTRODUCTIONTO ORGANIC CHEMISTRYCHAPTER 1

Welcome to ChemistryThe study of the composition of matter and the changes it undergoes

The study of the composition of matter and the changes it undergoes

IS THIS WHAT YOU THINK?

The study of the composition of matter and the changes it undergoes

Chemistry is Life

Can you identify organic compounds from this picture?

Road surface (bitumen)Fuel in carTyre

What is Organic chemistry?

TOPIC 1.1Chemistry of Carbon

InorganicOrganic

Some Brief HistoryMr Friedrich WhlerBorn: 31-Jul-1800Birthplace: Eschersheim, GermanyDied: 23-Sep-1882

He changed the belief that organic compounds could only be made by living things.Organic compounds are compounds that contain the element Carbon (C).Most organic compounds also contain hydrogen (H).Organic compounds that contain only carbon and hydrogen are called hydrocarbons.

Q: Do all compounds containing carbon considered as organic compounds?

A: No. Chemists consider carbonates and oxides of carbon as INORGANIC compounds rather than organic.

Question Time!

Organic chemistry is the chemistry of carbon compound.Basic for all life.Example : methane, DNA, urea, DDT (insecticide), penicillin , nicotine, aspirin etc..

But not all carbon compounds are organics.

Example : carbonate (CO32-), cyanide (CN-), bicarbonate (HCO3-), carbon dioxide (CO2) and carbon monoxide (CO).

What is organic chemistry?

Why is it so important? Think about how organic compounds affect our daily life: Our clothes natural and synthetic fibers Our medicines Our food carbohydrates, proteins, triglycerides Oils, perfumes, paints, plastics, detergents, etc.

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Organic Compounds

Typical organic compounds

have covalent bonds.have low melting points.have low boiling points.are flammable.are soluble in non-polar solvents.are not soluble in water.

A covalent bond is a chemical bond that involves the sharing of electron pairs between atoms. The stable balance of attractive and repulsive forces between atoms when they share electrons is known as covalent bonding12

Some organic chemicals

DNAMaterialsEssential oilsFuelsPigments

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Organic vs. Inorganic

Propane, C3H8, is an organic compound used as a fuel.

NaCl, salt, is an inorganic compound composed of Na+ and Cl- ions.

Inorganic chemistry is the study of the synthesis and behavior of inorganic and organometallic compounds. This field covers all chemical compounds except the myriad organic compounds (carbon based compounds, usually containing C-H bonds), which are the subjects of organic chemistryMany inorganic compounds are ionic compounds, consisting of cations and anions joined by ionic bonding. Examples of salts (which are ionic compounds) are magnesium chloride MgCl2, which consists of magnesium cations Mg2+ and chloride anions Cl; or sodium oxide Na2O, which consists of sodium cations Na+ and oxide anions O2.14

Comparing Organic and Inorganic Compounds

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Naturally Occurred Organic CompoundsName Of OrganicCompoundsOriginUsageProteinsExample :a) Enzymesb) HormonesFrom animalsa) As a structural materials.b) As a biological catalyst and regulators.Fats and OilsExample :a) Triglyceride b) Paraffin Oils c) Almond OilsFrom animals and vegetablesTo store energy.VitaminsExample :A,B Complex, C, D, E and KFrom foodFor healthy growth and functioning.

Synthetic Organic CompoundsItemsExamplesUsagePlasticsPoly (ethene), Perspex.For packaging, plastic bags, as a substitute for glass.Medicines andDrugsTranquilizer, Analgesic and Bactericide.To treat tropical diseases such as Trypanosomiasis or Sleeping Illness and Malaria.PesticidesDichlorodiphenyl trichloroethane( DDT )To kill houseflies and other insects.DyesMethylene blueGive colour to the material.

C

Why carbon? A carbon atom forms four bondsCarbon atoms form stable bonds with other carbon atoms (i.e., the CC covalent bond is strong)Can form chains and even networks Examples: graphite and diamond

carbon612.011

Position of Carbon

Chemical FormulasOrganic compounds can be complexA system is needed that shows structure. We want something that is easy to read. Molecular formula Empirical formula Structural formula Condensed formula Bond-line formula

Is a shorthand notation to represent the ratio of atoms of elements in a compound. 20

Molecular formulaActual number of atoms of each element in a molecule.

Empirical formulaSimplest ratio number of atoms of each element in a molecule.

Example: Glucose, C6H12O6C6H12O6Molecular formulaCH2OEmpirical formula

An emprical formula simplest ratio of atom of each element that made up a compound.21

Learning Check!1. Write the emperical formula for the following molecules:

glucose, C6H12O6Benzene, C6H6Oxalic acid, C2H2O4

2. After exercise, lactic acid is formed in the muscles, making a person tired. An analysis shows that lactic acid contains 40.0% C, 6.71% H & 53.5% O by weightCalculate the emperical formula of lactic acid.Calculate the molecular formula of lactic acid[Mr of lactic acid is 90.08; C:12 , H:1 , O:16]

Expanded @ Structural FormulaShow all atoms in the bondsBonds represents as linesExamples:

Propane

Condensed Structural Formula

A Type of line formatShorthand way of writing formulaList of atoms in order and tells how there are bound togetherExample:

Propane CH3CH2CH3

Bond Line @ Skeleton Formula

Represent structure by showing bonds between carbons and atoms other than hydrogen.Atoms other than carbon and hydrogen are called heteroatoms.ExampleCH3CH2CH2CH3 is shown asCH3CH2CH2CH2OH is shown as

OH

Learning Check!C

C

HHHHHHC2H6 Molecular formulaCH3Empirical formulaCH3CH3Condensed formulaStructural formulaExample: Ethane

Learning Check!Structural formulaExample: PentaneC

HHHC

C

HHHHHC

C

HHHHC5H12Molecular formulaCH3(CH2)3CH3orCH3CH2CH2CH2CH3Condensed formula

Bond-line formula

TOPIC 1.2 : Types of Organic CompoundCHAPTER 1

Types of Organic CompoundORGANIC COMPOUND

ALIPHATICALICYCLICAROMATICOPEN chains of carbon atoms. Unbranched or Branched Contain Single, Double or Triple bonds. Example: ethane (CH3CH3) ethene / ethylene (CH2=CH2) ethyne / acetylene (CHCH) CLOSE rings of carbon Atoms. Rings form the shape of POLYGON (triangle, square, rectangle or etc).CLOSE rings of carbon atoms. Contain a benzene ring. Example: Benzene

Types of Organic CompoundORGANIC COMPOUNDALIPHATIC

SATURATEDUNSATURATED

Compound that contains only single bond.

Example: alkaneCompound that contains multiple bond.

Example: alkene, alkyneC

C

HHHHHHCC

HHHHHCCH

TOPIC 1.3 : Types of ReactionCHAPTER 1

Type of Organic Reaction

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General Reaction

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Type of Organic Reaction: AdditionTwo substances react together to form a single substance.Addition of HBr to an alkene

Hydrogen BromideEthaneBromoethane

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Type of Organic Reaction: SubstitutionAn atom or a group (leaving group) in a molecule is replaced by another atom or group (nucleophile / electrophile). SN2 reaction

Hydroxide ion (nucleophile)(leaving group)BromobutaneButanolBromide ion

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Type of Organic Reaction: EliminationRemoval of atoms or groups of atoms from a saturated molecule to form an unsaturated molecule.Dehydration of alcohol

CH3CH2CH2CH2OHButanolH2SO4

CH3CH2CH=CH2 + H2OButene

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Type of Organic Reaction: RearrangementMigration of an atom, a group of atoms or a bond from one atom to another within molecule to form its isomer.Tautomerism of keto-enol

CH3CCH2

OH

PropenolCH3CCH3

O

Propanone

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Specific Reaction

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Type of Organic Reaction: HydrogenationAddition of hydrogen to a multiple bond to form a single bond substance. Hydrogenation of alkane

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Type of Organic Reaction: EsterificationAcid-catalyzed ester formation between alcohol and carboxylic acid.Fischer esterification

CH3COCH2CH3

O+H2OCH3COH

O+CH3CH2OH

H2SO4refluxEthanoic acidEthanolEthyl ethanoate

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Type of Organic Reaction: OxidationAn increase in the number of bonds between carbon and oxygen and/or a decrease in the number of carbon-hydrogen bonds.

Oxidation of methane

CH42O2+

CO22H2O+MethaneOxygenCarbon dioxideWater

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Type of Organic Reaction: HydrolysisChemical process in which a molecule is split into two parts by the addition of a molecule of water.

(CH3)3CBr + H2O

(CH3)3COH + HBrtert-Butyl bromidetert-Butyl alcoholHydrogen bromide

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