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Organic Chemistry Alkanes and Fuels

Introduction
Organic Chemistry is the chemistry of carbon compounds. However, simple carbon compounds such as carbon dioxide, carbon monoxide and metal carbonates are classified as inorganic. The word ORGANIC means from living things, because carbon compounds were first obtained from plants and animals. Organic compounds are found in all animals and plants.

Bond formation of carbon


lectronic structure of carbon is !!!!!!!!!!!!!!!!!!!!!!!!!. Hence an atom of carbon has 4 valence electrons and it can form 4 ___________bonds by !!!!!!!!! electrons with " other atoms #usually hydrogen, oxygen, nitrogen, sulfur and halogens$. xamples of compounds formed by carbon%

Classification of Organic Compounds Organic compounds are divided into hydrocarbons and non&hydrocarbons. Hydrocarbons are compounds that contain the elements hydrogen and carbon only. The non&hydrocarbons contain other elements, such as oxygen or chlorine, other than hydrogen and carbon. Homologous series Organic compounds are classified into families of compounds 'nown as homologous series. ( homologous series is a family of organic compounds with similar chemical properties. Compounds in the same homologous series have the following properties. They a$ b$ c$ d$ e$ have the same general molecular formula. are different from the next member by a &CH) group. show a gradual change in physical properties, for example, the melting point and boiling points rise gradually as the number of carbon atoms in the molecules increases* viscosity of members of the same homologous series increases as their si+e and mass increase. can be prepared using similar methods. have similar chemical properties because they have the same functional group.

xamples of homologous series include al'anes, al'enes, alcohols, and carboxylic acids and esters.
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( functional group is any atom or group of atoms that gives the characteristic properties to a molecule. Complete the following table. Name ending &ane &ene &ol &oic acid &oate Homologous series (l'ane (l'ene (lcohol Carboxylic acid Carboxyl group ster ster group Classifying and Naming Organic Compounds" The naming of organic compounds is divided into two parts% a$ the first part tells the chain length, which is the number of carbon atoms Name start #ith meth& eth& pro& but& Chain length $Number of carbon atoms% , ) " . / b$ The second part of the name shows the homologous series of the compound. xample thane% 0utanol (n !!!!!!!!!!!!! with !!!!!!! carbon atoms (n !!!!!!!!!!!! with !!!!!!!! carbon atoms !unctional group Carbon&carbon double bond Hydroxyl group

Al&anes
,. (l'anes are a group of saturated hydrocarbons with a general formula CnH'n(' ) where n is the number of carbon atoms in one molecule. Hydrocarbons are compounds which contain SYK/Sec 4 Chemistry/2012 '

hydrogen and carbon only. The molecular formula can be wor'ed out by using the general formula. ). (ll the names of al'anes end in &ane, eg. methane, ethane, propane, etc. The first " members of the al'ane family are shown below. Complete the table. Name *olecular !ormula CH" !ull +tructural formula
H

,hysical state at room temperature 2as

1ethane

C H

H C H H

thane

C)H/

C H

2as

3ropane

2as

0utane

gas

(l'ane with . carbon atoms 4 !!!!!!!!!!!!!!!* (l'ane with / carbon atoms 4 !!!!!!!!!!!!!! (l'ane with 5 carbon atoms 4 !!!!!!!!!!!!!!!* (l'ane with 6 carbon atoms 4 !!!!!!!!!!!!!! (l'ane with 7 carbon atoms 4 !!!!!!!!!!!!!!!* (l'ane with ,8 carbon atoms 4 !!!!!!!!!!!!!! -. (l'anes are often described as saturated because they have only carbon&carbon and carbon& hydrogen single bonds and thus contain the maximum possible number of hydrogen atoms per carbon.

,roperties of Al&anes ,. ). (l'anes are co-alent compounds. They have low boiling points, most of them are gases or li9uids at room temperature. :hy; .

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(l'anes have !!!!!!!!!!!!!!!!!!!!! structures. The !!!!!!!!!!!!!!!!!!!!!!!! forces between the !!!!!!!!!!!!!!!!!! are wea' and only a small amount of !!!!!!!!!!!!!! is needed to overcome these wea' forces. Hence the boiling points of al'anes are generally low. -. (s the number of carbon atoms in a molecule increases, the boiling point becomes !!!!!!!!!. (l'anes are !!!!!!!!!!!!!!! molecules. The intermolecular forces between the molecules are !!!!!!!!!!!!!!!!!!!!!!!!!!!. (s the carbon chain gets longer, the no. of !!!!!!!!!!!!!! increases, resulting in !!!!!!!!!!! !!!!!!!!!!!!! forces between the molecules, hence boiling point increases. (s the number of carbon atoms in a molecule increases, the al'ane become more viscous, ie. more difficult to flow. This is because long carbon chains are much more li'ely to get tangled up. This ma'es it difficult for the li9uid to flow. (s the number of carbon atoms in a molecule increases, the percentage of carbon in the al'ane molecule also increases. Thus the al'ane becomes less flammable or more difficult to burn and the flame becomes smo'y. The smo'y flame is caused by the incomplete combustion of carbon atoms. (l'anes are !!!!!!!!!!!!!!!!!!!! in water. (l'anes are usually !!!!!!!!!!!!!! dense than water.

".

..

/. 5.

Chemical Reactions of Al&anes


(l'anes are saturated hydrocarbons . <eactions of al'anes are% " Combustion

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(l'anes are fairly unreacti-e except that they can burn easily. :hen combustion is complete, that is, carried out in presence of e/cess oxygen, al'anes burn to give carbon dioxide and water. .g , CH" #g$ = )O) #g$ )H)O #g$ = CO) #g$

.g )% Combustion of butane !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! (l'anes are mostly use as !!!!!!!!!!. They produce energy when burnt. :hen combustion is incomplete, that is when the supply of oxygen is inade9uate, the products are carbon monoxide, soot and !!!!!!!!!!!!. xamples are% )CH" = -O) !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! Or CH" = O) !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! ). +ubstitution #ith halogens (l'anes react with halogens #fluorine, chlorine, bromine$ in the presence of >? light. >? light is needed to start the reaction. The light energy is used to brea' the covalent bond in the chlorine molecule to produce chlorine atoms or radicals% Cl & Cl !!!!!!!!!!! The chlorine radicals then react with the al'ane molecule. 0/ample 1 substitution reaction of methane #ith chlorine CH" #g$ 1ethane Or = Cl) #g$ chlorine !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!

e9uation showing full structural formula%

@n this substitution reaction, a hydrogen atom in methane is replaced by a chlorine atom. A substitution reaction is a reaction in which one or more atoms of an organic compound are replaced with one or more other atoms. 1ore hydrogen atoms of the methane can be replaced with chlorine atoms. The reactions are as follow%

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Hence all the products of the substitution of methane with chlorine are%

Isomerism
:or' out the molecular formula of the following al'anes. H H C H H C H H C H H C H H H H C H H !!!!!!!!!!!!!!!!!!! C H C H C H H H

H !!!!!!!!!!!!!!!!!!!

:hat do you notice about the molecular formula and structural formula of both al'anes; They both have the same !!!!!!!!!!!!!!!!!!!!!!!!!! but different !!!!!!!!!!!!!!!!!!!!! !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!. They are 'nown as isomers.

Isomers are compounds with the same molecular formula but with different structural formulas (different arrangement of atoms). Isomers have different physical properties such as boiling points . Isomerism is the existence of two or more compounds with the same molecular formula but different structural formulae.
The number of isomers increases as the number of carbon atoms in a molecule increases. @somers are also formed by other types of organic compounds, such as al'enes and alcohols.
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@somerism is important in petrol fuel for motorcars. The petrol from the fractional distillation of petroleum contains a lot of straight&chain al'ane molecules, such as octane% H H C H H C H H C H H C H H C H H C H H C H H C H H

>nfortunately, car engines do not run smoothly when burning such straight&chain molecules. The engines run much better when burning branched&chain isomers such as the isomer of octane below%
H H H H C H H C H C C H H C H H H H C C H H C H H H
To put more branched&chain isomers into petrol is expensive. @n the past, lead compounds are added to ma'e car engines run smoothly. Aue to lead pollution, this method is phased out. Bead&free petrol contains a large amount of branched&chain isomers.

3ractice , , a$ :or' out the molecular formula of pentane, an al'ane with . carbons. !!!!!!!!!!!!!!!!!!!!! b$ :or' out full structural formula of pentane.

c$

Araw the full structural formulas of all the isomers with the formula C.H,). 4

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).

Araw the full structural formulas of two isomers with molecular formula C)H"Cl)

-.

:hich of the following compounds are the same; H H C H H C H A H H H C C HH H C H C C H H H H H C H H H C H H C H H H H C H H C H C H H

HH C B H C C H D H

H C H H H

(nswer% !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!

5#o Important Industrial ,rocesses


,. !ractional 6istillation of petroleum" Crude oil or petroleum was formed from the remains of small marine animals and plants that were buried in the sea beds millions of years ago. 3etroleum or crude oil is a complex mixture of hydrocarbon molecules. 3etroleum must be separated into fractions before it can be useful. The different components in the crude oil have different boiling points and fractional distillation separates the components as a result of this property. ach fraction consists of a mixture of hydrocarbon molecules that boil over a range of temperature. The petroleum is heated in a furnace to about -/8CC in the absence of air to turn it into a vapour. The oil vaporises and passes up the fractionating column. The fractions come out of the column at different heights depending on their boiling points. 1olecules with longer carbon
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chains #higher relative molecular mass$ have higher boiling point than molecules with a shorter carbon chains #lower relative molecular mass$. Hence molecules of shorter carbon chains such as petroleum gas escape from the top of the fractionating column as gases. The hydrocarbon with longer carbon chains condense into a li9uid and are collected from the lower sections of the column.

!raction 3etroleum gasDEatural gas 3etrol #gasoline$ Eaphtha Ferosene #parrafin$ Aiesel oil Bubricating oil 0itumen ).

Boiling Range $8C% 0elow "8 "8&5. 5.&,.8 ,/8&).8 ).8&-88 -88&-.8 (bove -.8

Number of carbon atoms per molecule ,&" .&,8 5&," ,,&,/ ,/&)8 )8&-. 1ore than 58

Crac&ing of Big Al&ane *olecules Crac'ing is a process which involves splitting larger hydrocarbon molecules of higher boiling fractions into smaller molecules of lower boiling fractions by subGecting them to high temperature and pressure, usually in the presence of a solid !!!!!!!!!!!!. The process is 'nown as catalytic crac'ing when a catalyst is used. On the industrial scale, crac'ing is done by passing the petroleum fraction containing long chains of carbon atoms over aluminium oxide or silicon #@?$ oxide catalyst at a temperature of about /88C. Barge hydrocarbons

short&chain al'anes = short&chain al'enes


= !

.g C,,H)" H C)H" 9ses of Crac&ing


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!!!!!!!!!!!!!!!!!!!!!!!!!

,.

Our need for petrol is greater than our need for diesel oil or lubricating oil. The less useful large molecules #e.g diesel$ are crac'ed to form smaller molecules #e.g petrol$ as there is a great demand for the smaller molecules. Crac'ing is a way of ma'ing short&chain al'enes such as ethene and propene and the al'enes obtained are used to ma'e plastics.

).

.g. C,6H-6 H ( big al'ane

C/H," = a smaller al'ane

/C )H" / ethene molecules #used to ma'e ethanol and plastics$

-.

Crac'ing produces hydrogen gas as a by&product in oil refineries. The hydrogen can be used to ma'e ammonia by Haber process.

.g. C,6H-6 H C,6H-/


".

H'

Crac'ing tends to produce branched&chain rather than straight&chained al'anes, hence providing petrol with higher octane rating.

Crac&ing in the laboratory


Catalytic crac'ing can be demonstrated in the school laboratory using the apparatus shown below. The bro'en pot which contains aluminium oxide and silicon #@?$ oxide acts as a !!!!!!!!!!!!. The main gaseous product is ethene.

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Naming of organic compounds 1 Nomenclature Eaming of organic compounds follows the rules laid by @>3(C #@nternational >nion of 3ure and (pplied Chemistry$. <ules in naming% ,. The name ending for different homologous series is different. Ior example, The name ending for all al'anes is !!!!!!!!, e.g. !!!!!!!!!!!!!!! The name ending for all al'enes is !!!!!!!!!!!, e.g. !!!!!!!!!!!! The name ending for all alcohols is !!!!!!!!, e.g. !!!!!!!!!!!!! The name ending for all carboxylic acid is !!!!!!!!!!!!!!!, e.g. !!!!!!!!!!!!!!! ). Jelect the longest continuous chain of carbons in the structure as the parent chain. Ior eg CH3 CH3CH2CHCH2CH2CH3 No" of C atoms in parent chain CH2CH3 CH3CH2CH2CH2CHCH3

-.

The carbon atoms of the parent chain are numbered #,, ), -, K$ to give the position of the substituent group #e.g. an al'yl group$ and functional group along the chain, the numbering is such that the lowest possible numbers appear in the name.
Naming of substituent groups as follow: -CH3 methyl -C2H5 ethyl -C3H7 propyl -Cl chloro -Br bromo -F fluoro -OH hydroxy -NO2 nitro !"

CH3 CH3CH2CHCH2CH2CH3

".

@f the same substituent group occurs more than once, multiplier prefixes are used% ) " di& tri& !!!!!!!!! . / 5 penta& !!!!!!!!! !!!!!!!!!

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The location of every group must be named according to numerical order. (lways separate a number from another number in a name by a comma.
!"!

CH3

CH3

CH3CHCH2CCH3 CH3

..

@f two or more different substituent groups are attached to the parent chain, they are named in alphabetical order. Eames of substituent groups are alphabeti+ed before any prefixes such as di& or tri& are affixed. Hyphens are used to separate numbers from words. .g.
C2H5 CH3 CH3CH2CH2CHCH2CCH3 CH3

,ractice ' Eame the following compounds%


#!

H H C H
2!

CH3 H C H C H

H C H

H C H H

H H C H
3!

H C H

CH2CH3 H C H C H

H C H H

CH2CH3 H H C H C H C H H C H H '

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$!

CH3CHCHCH2CH2CH3 Cl Br H CH3 H C C H C H H C H H

5!

C H

CH3 H

%!

H H C H

CH3 H C C

CH3 H C C H

CH3 H

CH3 H

5.

CH3

CH2

CH2 CH3

6.
H H H C H

H C H H C H C H H

0nrichment < ree !a"ical Substitution #echanism $e%emplifie" by methane& The mechanism ta'es place via three stages & initiation, propagation and termination. :hen >? light or sunlight is shone on the reaction mixture, chlorine molecules are supplied with enough energy to split them into radicals. 0ond energy #Cl)$ 4 )") 'L mol&,
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The chlorine molecules undergoes homolytic fission to produce radicals.


Cl Cl

C&H bond in al'anes is not bro'en instead as bond energy #C&H$ 4 "-. 'L mol&, is too high.
CH$ CH3 = H

+tage ' 1 ,ropagation The chlorine radicals formed are highly reactive. :hen they collide with an al'ane molecule, they abstract an hydrogen atom from the al'ane molecule, forming an al'yl radical in the process.
Cl = CH$

The al'yl radical then reacts with another chlorine molecule to form more chlorine radicals. These two reactions enable a chain reaction to occur, hence MpropagatingM the reaction. +tage . 1 5ermination !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! :hen two radicals collide, a stable bond is formed. The reactions are highly exothermic as they involve bond forming only. Trace amounts of ethane are formed as by&products.

0nrichment < Naming compounds #ith more than functional group


@dentifying the suffix The suffix identifies the principal functional group which the molecule belongs to. (n organic molecule with more than one functional group would be named with the functional group highest in the priority list. The functional groups in accordance to priority are !unctional group ster Carboxylic acid (lcohol (l'ene (l'ane Name as a suffi/ &oate &oic acid &ol &ene &ane Name as a prefi/ & Carboxy Hydroxy

The carbon atom which the functional group of the highest priority resides on is assigned the smallest possible position number #usually ,$.
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Identifying the prefi/$es% and locants 3refixes are used if there is more than one functional group or when there are al'yl braches on the organic molecule. ach prefix is preceded by a number called the locant, which states the position of the functional group or al'yl chain relative to the first carbon of the organic molecule. :or'ing out the name of this compound H H C H OH C H H C H C O O H

&he c'rbon (hich the hi"he)t priority function'l "roup re)ide) on i) l'belled c'rbon no! # or C#! This organic molecule has four carbons. The root of this compound would be butyl. @n this example, this organic molecule has two functional groups namely an alcohol group and a carboxylic acid group. (ccording to the list, a carboxylic acid ta'es higher priority in the nomenclature than an alcohol. Hence this compound would be named as a carboxylic acid. This compound would be named as a butanoic acid. The additional information that this molecule has an alcohol group is conveyed by the prefix#es$. @n this case, the alcohol group is on carbon no. - #C-$. Hence we add the prefix -&hydroxy to the root name. This compound is named as -&hydroxybutanoic acid.

+elf study +ection 1 !uels


A fuel is a substance that can be easily burnt in air to gi-e out energy" 3ower stations in Jingapore produce energy by burning fuels. The main fuels are petroleum #crude oil$, natural gas. Coal #mainly carbon$ is also an important fuel. ( lot of pollutants such as oxides of sulfur and nitrogen are produced when coal are burnt. Coal, petroleum and natural gas are called fossil fuels, they were formed from the remains of plants and animals that lived millions of years ago. :hen coal is strongly heated in the absence of air, a solid called co'e which is almost pure carbon is produced. Co'e burns more cleanly than coal&it does not produce as much smo'e. The main use of co'e is as a reducing agent in the blast furnace for ma'ing iron. Choice of !uels The properties of a good fuel are as follows% ,$ @t must be easy to ignite but not be so flammable as to cause any danger. SYK/Sec 4 Chemistry/2012 2

)$ -$ "$

@t must be easy to store and transport. @t must produce as little pollution as possible. @t must produce a lot of energy during combustion.

The three main fuels are compared in the table below. Coal 0ase of transportation and use 0ffect on en-ironment #hen burnt =orld reser-es $appro/imate amount remaining% ,etroleum $oil% Natural gas
1oderate* not easily ?ery good* easily moved 2ood* easily moved along moved along pipes* not along pipes* easily pipes, but must be easily controlled in use controlled in use li9uefied for shipment by sea* easily controlled in use. ?ery bad* large amounts 1oderate* little sulfur 2ood* methane burns of sulfur dioxide and soot dioxide and soot cleanly* no soot or sulfur produced. produced. dioxide produced. nough for )88&).8 nough for )8&"8 years nough for )8&.8 yrs years

Alternati-e 0nergy +ources Iossil fuels are non&renewable fuel, that is, there is only a finite amount in the earth and their supply is limited. They will eventually be run out. Hence it is necessary to find alternative sources of energy to replace fossil fuels. Jome (lternative Jources of nergy% ,. ). -. ". .. /. Jolar energy Jolar cells are costly. Jolar energy is clean and does not cost pollution. Tidal energy Hydroelectric power 0iogas which is the gas produced from organic matter #waste material from plants or animals$ is allowed to decay in the absence of air. 0iogas contains about .8N methane. Euclear power >sing hydrogen as a fuel Ad-antages> Hydrogen burns cleanly in air. The product is water and does not pollute the environment. The combustion of hydrogen is exothermic and produces a lot of energy. Bi9uid hydrogen is used as a fuel in space roc'ets. 3>0 gas, which is mainly hydrogen, is used for coo'ing. 6isad-antages> Hydrogen is a gas and cannot be easily li9uefied. Hence it cannot be transported as easily as solid and li9uid fuels. Hydrogen is a serious fire ris'. 1ixture of hydrogen and air are explosive.

SYK/Sec 4 Chemistry/2012

SYK/Sec 4 Chemistry/2012