Organic Chemistry

Organic compounds are compounds from living things and living organisms. A homologous series is a family of organic compounds with a general formula and similar chemical properties. Functional groups are the special groups of atoms in a homologous series responsible for the chemical properties of the compound. I.e: Alkenes = Ester Alcohol = Carboxlic acid Amide = =

Isomers are compounds with the same molecular formula but have different structural arrangement (and therefore also differ in physical and chemical properties*) Petroleum / Oil refinery Main source of alkanes and alkenes Products & Uses of Petroleum refinery LPG Fuel to heat appliances Gasoline Car fuel Naphtha Feedstock to produce gasoline Kerosene Jet fuel, cooking and lighting (Paraffin) fuel Diesel Fuel for buses, taxis, ships Lubricating Oil As name suggests Bitumen Road construction (Asphalt)

Properties of organic compounds across homologous series (i.e alkanes) No of C Name Boiling Points Viscosity / Density Methane 162 1 Ethane 2 89 M.P/B.P As size increases, Propane 3 42 increase due to stronger Butane 4 0 s as size van der Waals Pentane 5 36 increase forces, viscosity Hexane 6 69 increases Heptane 7 98 Octane 8 126

Flammability

Flammability decreases as size increases, more soot produced during combustion

More alkane members* 9 = Nonane 13 = Tridecane 10 = Decane 14 = Tetradecane 11 = Undecane 15 = Pentadecane 12 = Dodecane 16 = Hexadecane

17 = Heptadecane 18 = Octadecane 19 = Nonadecane 20 = Eicosane

* Out of syllabus

2013 by Andy Lee (TAG)

Organic Chemistry Alkanes (Alkyl)

General formula: + Very stable, bonds cannot be easily broken. Free radicals play large part in most alkanes reactions. Insoluble in water, but soluble in organic solvents* Possesses no functional group

Nomenclature of Alkanes The names given above are for straight-chained alkanes. For branch-chained alkanes, we break down the alkane into its main chain and side chains. Pentane (n-pentane*) 2-Methylbutane (isopentane*) 2,2-Dimethylpropane (neopentane*) When an alkane is a side group, it becomes an alkyl group. We add the group as a prefix and use -yl for its name. In these cases, the methane molecules are side chains, thus are named as methyl-

We denote the positions of the side chains with a number on the larger chain Alkanes Reactions Name

Conditions

Reactions Complete combustion produces carbon dioxide and water 22 6

+ 72() 42() + 62 () + 52() 4() + 62 () + 32() 4() + 62 ()

Combustion

Air (Oxygen)

Incomplete combustion produces carbon monoxide or even soot 22 6 22 6

Halogen substitute hydrogen atoms away one by one. A mixture of products produced 4 + 2 3 + chloromethane 3 + 2 2 2 + dichloromethane 2 2 + 2 3 + trichloromethane tetrachloromethane 3 + 2 4 + If larger alkanes are used, a mixture of isomers will be produced. Bromine substitution is slower than chlorine. Iodine doesn't react under lab conditions and Florine reactions are explosive, even in the dark Breaks down larger hydrocarbons into smaller ones. There are many more uses for smaller hydrocarbons than larger ones. 15 32 22 4 + 3 6 + 8 18
* Out of syllabus

Substitution Reaction (Free radical halogenation)

UV light (Photochemical reaction)

Cracking

Depends*

2013 by Andy Lee (TAG)

Organic Chemistry Alkenes

General formula: Insoluble in water, but soluble in organic solvents Possesses functional group of = Nomenclature of Alkenes When naming alkenes, it is important to take note of where the functional group is. Because the carbon-carbon double bond doesn't allow any rotation about it, the position of the hydrogen atoms in 3D space also has to be accounted for* No of C Name Structure Ethene 2 = Propene 3 = 4 Butene = But-1-ene = But-2-ene = Methylpropene

Production of Alkenes Cracking of long-chain alkanes Dehydration of alcohols using either aluminium oxide or concentrated Alkenes Reactions Name

or 2 4

3 4 as catalyst

Conditions

Reactions Complete combustion produces carbon dioxide and water 2 4

+ 32() 22() + 22 ()

Combustion

Air (Oxygen)

Incomplete combustion produces carbon monoxide or even soot

2 4

+ 22() 2() + 22 ()

2 4 Addition Reaction (Electrophilic addition)

+ 2() 2() + 22 ()

R.t.p

2 = 2 + 2 2 2 Adding an alkene to bromine water decolourises it because the brown bromine molecules react with the alkene. (forms mixture*) Alkenes react with chlorine and iodine similarly. Alkenes hydrogenate to become alkanes. 2 = 2 + 2 3 3 This reaction is not useful as alkenes generally are more useful than alkanes. However vegetable oils are hydrogenated to produce margarine. Vegetable oils have high number of carbon-carbon double bonds, and the more carbon double bonds, the lower the melting point. As a result vegetable oils are liquid at r.t.p and messy to spread. Hydrogenating it raises the m.p and give them better texture. 2013 by Andy Lee (TAG)

Hydrogenation

Nickel Catalyst ~

* Out of syllabus

Alkenes react with pure liquid bromine, breaking up the carboncarbon double bond

Organic Chemistry
Name Conditions Reactions Ethanol is manufactured by reacting steam with excess ethene. The reaction is reversible. 2 = 2 + 2 () 3 2 () Hydration Phosphoric (V) acid This reaction is reversible. Only 5% of the ethene is converted. 60 - 70 atm The gases are cooled and both water and liquid ethanol are ~ separated through fractional distillation. Thus ethanol is removed from the equilibrium mixture and ethene is recycled, allowing an overall 95% conversion. acidified Potassium Produces a mixture of diol, ketone, carbon dioxide and carboxylic manganate (VII), hot acid Thousands ethene molecules undergo addition polymerisation to form a single product, polyethene. Depends* =

Oxidation* Addition Polymerisation

Polymers of alkenes* Name Conditions Low Density Polyethene (LDPE) High Density Polyethene (HDPE) 2000 atm ~200 <10 atm Ziegler-Natta catalysts

Properties & Uses Used as plastic bags and other similar low strength, flexible sheet materials

Used to make plastic milk bottles, washing up bowls, plastic pipes

There are many uses depending on the structure of the produced poly(propene) (arrangement of the 3 3D space) in Poly(propene) <10 atm Ziegler-Natta catalysts Some uses range from: plastic crates, ropes, roofing felt, plastic film for food wrap, in medical tubes Uses include guttering, plastic windows, electrical cable insulation , sheet materials for flooring, footwear, clothing

Poly(vinyl chloride) (PVC)

Poly(tetrafluoro ethene) (PTFE)

Used in chemical and food industries to coat vessels, used to make non-stick kitchen and garden utensils

* Out of syllabus

2013 by Andy Lee (TAG)

Also named as Teflon, due to the electronegativity of F, resistant to almost everything.

Organic Chemistry Alcohol

General formula: + Small alcohols are soluble in water, solubility falls as size increases (4 carbon and up) Possesses functional group of Manufacturing alcohol Name Conditions Hydration of Alkene

Reactions Refer to alkenes Method only capable of producing ethanol. Source: Glucose, starch, sucrose, maltose, almost any carbohydrates, even sugar cane also can

Fermentation

Yeast catalyst, Absense of air

6 12 6 2 5 + 22 Yeast is killed by ethanol concentrations of > 15%, limiting the purity of ethanol produced. Ethanol is separated by fractional distillation, yielding about 96% pure ethanol. Theoretically, it is impossible to remove the last 4% of water by fractional distillation

Alcohols Reactions Name Combustion

Conditions Air (Oxygen)

Reactions Complete combustion produces carbon dioxide and water 2 5 () + 32() 22() + 22 () Incomplete combustion produces carbon monoxide or even soot Ethanol vapour is passed over heated aluminium oxide powder to form ethene 2 5 2 = 2 + 2 Primary* alcohol is oxidised into a carboxylic acid through a 2-step process. (first the alcohol is partially oxidised into an aldehyde then fully oxidised into carboxylic acid)* 2 5 + 2[] 3 + 2 In the body, alcohols are oxidised into carboxylic acid through enzymes, and alcohols are also oxidised in the atmosphere* Reaction is slow and reversible.

Dehydration

Aluminium oxide catalyst

Oxidation

acidified potassium dichromate (VI)

+ 3 2 3 + 2 2 3 Esterification conc sulphuric acid Esters are produced in the lab by warming both the acid and alcohol with a few drops of concentrated acid. Esters smell sweet, but are often masked away by the smell of the acid. Pour the mixture into a beaker of water to dissolve any excess acid and alcohol to detect the smell of ester. Hydrolysis of an ester is the exact reverse reaction, producing a carboxylic acid and an alcohol
* Out of syllabus

2013 by Andy Lee (TAG)

Organic Chemistry Carboxylic acids

Has all the physical and chemical properties of an acid Are weak acids, i.e roughly only 0.4% of ethanoic acid dissociates in water Possesses functional group of Formation of carboxylic acids Refer to oxidation of primary alcohols Carboxylic Acids Reactions Name Conditions Combustion Neutralisation With metal With carbonates Esterification Air (Oxygen)

Reactions Complete combustion produces carbon dioxide and water 3 () + 22() 22() + 22 () Incomplete combustion produces carbon monoxide or even soot Refer to notes on acid, bases and salt Refer to notes on acid, bases and salt Refer to notes on acid, bases and salt Refer to notes on alcohols reactions

* Out of syllabus

2013 by Andy Lee (TAG)