Organic: module 1 revision guide

Hydrocarbon is a compound consisting of hydrogen and carbon only

Basic definitions to know

Saturated: Contain single carbon-carbon bonds only

Unsaturated : Contains a C=C double bond

Petroleum fraction: mixture of hydrocarbons with a similar chain length and boiling point range

Molecular formula: The formula which shows the actual number of each type of atom

Empirical formula: shows the simplest whole number ratio of atoms of each element in the compound General formula: algebraic formula for a homologous series e.g. CnH2n Structural formula (displayed formula): show all the covalent bonds present in a molecule Homologous series are families of organic compounds with the same functional group and same general formula. They show a gradual change in physical properties (e.g. boiling point). Each member differs by CH2 from the last. same chemical properties. Functional group is an atom or group of atoms which when present in different molecules causes them to have similar chemical properties

Drawing Displayed formulae

H H C H H C H H H C H C H H C H H

When drawing organic compounds add the hydrogen atoms so that each carbon has 4 bonds

Remember that the shape around the carbon atom is tetrahedral and the bond angle is 109.5o

H H H C C

H H H

Group of compounds Alkane Alkene

General formula

Functional group

Naming compound (suffix)(prefix-) -ane -ene Halo[Fluoro-, Chloro-, Bromo-, Iodo-]

Example Name Butane Propene Structure CH3CH2CH2CH3 CH2=CHCH3

CnH2n+2 CnH2n CnH2n+1X

C

Haloalkane

-X where X = F, Cl, Br, I

1-bromobutane

CH3CH2CH2CH2Br

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General rules for naming carbon chains

Count the longest carbon chain and name appropriately Find any branched chains

code meth

no of carbons 1 2 3 4 5 6 7 8 9 10

General rules for naming functional groups

The functional group is indicated by a prefix or suffix. e.g. chloroethane
H H C3 H Br C2 H H C1 H H

The position of the functional group is given by a number counting from the end that gives the functional group the lowest number.
H H C H H C H H H C H C H H

We only include numbers if they are needed.

Where there are two or more of the same groups, di-, tri- or tetra are used and . Words are separated by numbers with dashes If there is more than one functional group/substituent, numbers are separated by commas and the groups are listed in alphabetical order (ignoring di, tri, etc.).

s e xiff u s r e ht o f o t n o rf ni o g n a c s e n e kl a r of xiff u s e h T

niatnoc yeht snobrac ynam woh tnuoc dna

3,5-dimethyl heptane
H C4 H

eth prop but pent hex hept oct non dec

niahc hcnarb hcae rof xiferp etairporppa eht ddA

methyl propane

lyporp 7H3C lyhte 5H2C- ro lyhtem 3HC- gE

CH2Cl2
Br CH3 CH CH3 C Br CH3

2-bromobutane

dichloromethane

2,3-dibromo-2-methylbutane.

CH2ClCBr2CH2CH3 CH2ClCH2CHBrCH3 CH2OHCHClCH=CH2

2,2-dibromo-1-chlorobutane. 3-bromo-1-chlorobutane

2-chlorobut-3-en-1-ol

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Isomers Structural isomers: same molecular formula different structures (or structural formulae) Structural isomerism can arise from Chain isomerism Position isomerism Functional group isomerism Chain isomers: Compounds with the same molecular formula but different structures of the carbon skeleton
H
H H C H H C H H C H H C H H C H H

H H C H

H C H C H H

H C H

H C H
H

C C

H H C H H H

H
H

H C H

C H

pentane

2-methylbutane

2,2-dimethylpropane

position isomers: Compounds with the same molecular formula but different structures due to different positions of the same functional group on the same carbon skeleton
H H C Br H C H H

H C Br

Functional group isomers: Compounds with the same molecular formula but with atoms arranges to give different functional groups
H H C H H C H O H

H O C H H

ethanol: an alcohol

C H

Methoxymethane: an ether

H H C H C

H H C H

Cyclohexane- cyclo alkane

H H H H C C H C H

CH3CH2CH2CH2CH=CH2

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enaporpomorb-2 enaporpomorb-2 enaporpomorb-2 enaporpomorb-2

hexene- alkene

enaporpomorb-1 enaporpomorb-1 enaporpomorb-1 enaporpomorb-1

Refining crude oil Fractional Distillation: Oil is pre-heated Key points to learn then passed into column. The fractions condense at different heights The temperature of column decreases upwards The separation depends on boiling point. Boiling point depends on size of molecules. The larger the molecule the larger the van der waals forces Similar molecules (size, bp, mass) condense together Small molecules condense at the top at lower temperatures and big molecules condense at the bottom at higher temperatures. petroleum is a mixture consisting mainly of alkane hydrocarbons

Petroleum fraction: mixture of hydrocarbons with a similar chain length and boiling point range This is a physical process involving the splitting of weak van der waals forces

Vacuum distillation unit Heavy residues from the fractionating column are distilled again under a vacuum. Lowering the pressure over a liquid will lower its boiling point.

Vacuum distillation allows heavier fractions to be further separated without high temperatures which could break them down.

Cracking: conversion of large hydrocarbons to smaller molecules of by breakage of C-C bonds High Mr alkanes smaller Mr alkanes+ alkenes + (hydrogen)

Economic reasons for cracking The petroleum fractions with shorter C chains (e.g. petrol and naphtha) are in more demand than larger fractions. To make you of excess larger hydrocarbons and supply demand for shorter ones, longer hydrocarbons are cracked. The products of cracking are more valuable than the starting materials (e.g. ethene used to make poly(ethene), branched alkanes for motor fuels, etc.) This is a chemical process involving the splitting of covalent bonds

THERMAL CRACKING Conditions: HIGH PRESSURE ... 7000 kPa HIGH TEMPERATURE ... 400C to 900C PRODUCES MOSTLY ALKENES ... e.g. ETHENE for making polymers and ethanol PRODUCES HYDROGEN ... used in the Haber Process and in margarine manufacture Example Equations C8H18 C12H26 C6H14 + C2H4 C10H22 + C2H4

Conditions: SLIGHT PRESSURE HIGH TEMPERATURE ... 450C ZEOLITE CATALYST ZEOLITES are crystalline aluminosilicates; clay like substances PRODUCES BRANCHED, and CYCLIC ALKANES, and AROMATIC HYDROCARBONS USED FOR PRODUCING MOTOR FUELS Branched and cyclic hydrocarbons burn more cleanly and are used to give fuels a higher octane number Cheaper than thermal cracking because it saves energy as lower temperatures and pressures are used

Bonds can be broken anywhere in the molecule by C-C bond fission and C-H bond fission.

GN KCARC C TYLATAC GN KCARC C TYLATAC GNIIIIKCARC CIIIITYLATAC GN KCARC C TYLATAC

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COMBUSTION
Fuel : releases heat energy when burnt Alkanes readily burn in the presence of oxygen. This combustion of alkanes is highly exothermic, explaining their use as fuels.

.O2H dna 2OC era noitsubmoc etelpmoc fo stcudorp ehT

CH4(g) + 2 O2(g) CO2(g) + 2 H2O(l) If there is not enough oxygen then incomplete combustion occurs, producing CO (which is very toxic) and/or C (producing a sooty flame) Pollution from combustion in engines Sulphur containing impurities are found in petroleum fractions which produce SO2 when they are burned, which lead to acid rain. S+ O2 SO2 CH3SH+ 3O2 SO2 + CO2 + H2O SO2 can be removed from the waste gases from furnaces (e.g. coal fired power stations) by flue gas desulphurisation. The gases pass through a scrubber containing calcium oxide which reacts with the sulphur dioxide SO2 + CaO CaSO3 Pollutant Nitrogen oxides (formed when N2 in the air reacts at the high temperatures in the engine) Carbon monoxide Carbon dioxide Unburnt hydrocarbons (not all fuel burns in the engine) Catalytic converters These remove CO, NOx and unburned hydrocarbons (e.g. octane, C8H18) from the exhaust gases, turning them into harmless CO2, N2 and H2O. 2 CO + 2 NO 2 CO2 + N2 C8H18 + 25 NO 8 CO2 + 12 N2 + 9 H2O Global warming Carbon dioxide levels have risen significantly in recent years due to increasing burning of fossil fuels. Carbon dioxide is a particularly effective greenhouse gas and its increase is thought to be largely responsible for global warming.

Carbon dioxide (CO2), methane (CH4) and water vapour (H-2O) are all greenhouse gases (they trap the Earths heat in the atmosphere). Water is the main greenhouse gas (but is natural), followed by carbon dioxide and methane. The Earth is thought to be getting warmer, and many scientists believe it is due to increasing amounts of greenhouse gases in the atmosphere.

Some scientists disagree and think the suns activity is largely responsible for climatic variations

)l(O2H 2 + )s(C )g(2O + )g(4HC )l(O2H 2 + )g(OC )g(2O 2/3 + )g(4HC

Environmental consequence Can form acid rain toxic

Incomplete combustion produces less energy per mole than complete combustion

coal is high in Sulphur content, and large amounts of sulphur oxides are emitted from power stations.

The calcium sulphite which is formed can be used to make calcium sulphate for plasterboard.

Contributes towards global warming Contributes towards formation of smog

Converters have a ceramic honeycomb coated with a thin layer of catalyst metals Platinum, Palladium, Rhodium to give a large surface area.

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