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Unit09ORGANICCHEMISTRY

ScopeofOrganicChemistry

Introduction:

Observationofoursurroundingsshowwidevarietyoflivingstructures,delicious
fooditems,vibrantcolouredclothes,innumerableautomobiles,rangeofhealthfitness
medicines etc. The essence of all these is the element Carbon. It is wonderful to
understandtheformofcarboninalloftheabove.

Specialproperties:

Carbon has four electrons in the outermost orbit (tetravalent). Carbon shares
four valence electrons with other atom of carbon or with atoms of other elements to
formfourcovalentbondsinordertoattainoctetform.
Carbon also exhibits unique catenation property, by which carbon atoms are
linkedthroughacovalentbondtoformvariouskindsofchainofcarbonatoms.

Withtheadvantageoftetravalencyandcatenation,carbonformslargenumber
ofcompoundssuchthat,thenumberofcompoundsformedbycarbonalone,exceeds
numberofcompoundsformedbyalltheotherelementsintheperiodictable.

Definition:

Organic chemistry is chemistry of compounds of carbon. It is these

compoundsofcarboninvariousformsthatconstituteallaspectsofourlife.

Applications:

1. Food which comprises of carbohydrates (Glucose, sucrose, fructose etc), proteins

(aminoacids),oilsandfats(Glycerides)arecarboncompounds.
2. Clothesandfabricsmadeofcotton(cellulose),silk(woodpulp),Nylon(fromadipic
acidanddimethylamine),terylene(fromdimethylterphthalateandethyleneglycol),
acrylic(artificialwool)compriseofcarbonindifferentform.
3. Clothes are colourful due to dyes (colouring matter) which are yet again carbon
compounds Alizarin dye imparts red colour, indigoblue, malachite green,
Naphtholyellow.
4. Varioushydrocarbonslikepetrol,diesel,kerosenegasolineareenergysourcestorun
enginesinautomobiles.
5. Propellants,akindoffuelusedinrocketisamixtureoffuelandanoxidizer.

6. Application of organic compounds in usage of drugs in the field of medicine has

given rise to chemotherapy. To name a few, dettol (Chloroxylenol), salol are
antiseptics, penicillin, tetracycline are antibiotics, aspirin, despirin, novalgin which
reduce pain are analgesic, paracetamol, crocin used during fever are antipyretic,
antimalarialdrugslikechloroquin,quinineareusedtocuremalaria.
7. Petrochemicals are used as raw materials in the manufacture of polymers,
detergents,pesticidesandevenincosmetics.
8. Living protoplasm structures essentially found in animals and plants is made up of
carbon.Thecarbonleftbehindafterdeathordecayoflivingstructuresandmatter
isanevidencetoultimateroleofcarbonineverything.

FunctionalGroup:

Structural feature of carbon compound show carbon bonding with hydrogen

invariably and some time with hetero atom (different atom) like halogen, oxygen,
nitrogen, sulphur and phosphorous. Presence of hetero atom or group with
heteroatom, in the structure of carbon compounds confer specific properties to the
compound,hencearecalledfunctionalgroups.Thusfunctionalgroupisdefinedasan
atom or group of atoms that determines the characteristic properties of organic
compounds.

Examples:

Structure
Compound
Functionalgroup
H
Methylalcohol
OH:alcohol
HCOH
H

HO
HCCOH
H

Aceticacid

COOH:Carboxylicacid

Acetaldehyde

CHO;aldehyde

Methylchloride

Cl:chloro

HH
HCC=O
H

H
HCC l
H

Homologousseries:

Homologous series is the series of closely related compounds with similar

chemicalproperties.

Characteristics:

1.
2.
3.
4.

TheseseriesarerepresentedbyGeneralformula
TwosuccessivememberofseriesdifferbyCH2.
Theyarepreparedbycommonmethods
Showaregulargradationinphysicalproperties.

Example: Homologous series alkane has general formula CnH2n +2 and that of
alkene andalkyne, CnH2n and CnH2n2 respectively where n is number of carbon
atoms.

Alkaneseries
Name
MolecularFormula
Methane
CH4
Ethane
C2H6
Propane
C3H8
Butane
C4H10

Alkeneseries
Name
Ethene
Propene
Butene
Pentene

MolecularFormula
C2H4
C3H6
C4H8
C5H10

Alcoholseries
Name
Methanol
Ethano
Propanol
Butanol

MolecularFormula
CH3OH
C2H5OH
C3H7OH
C4H9OH

EmpericalformulaandMolecularformula:

Compoundsarerepresentedbyachemicalformulaandisoftwotypes
a)empiricalformula b)molecularformula

Emperical formula gives the simple whole number ratio of atoms of various
elementspresentinonemoleculeofthecompound.Example:Hydrogenperoxidehas
empirical formula HO, hydrogen and oxygen are in the ratio of 1 : 1. Glucose has
empiricalformulaCH2O,carbon,hydrogenandoxygenarepresentintheratioof1:2:1.
Molecularformulagivestheactualnumberofatomsofvariouselementspresent
in one molecule of the compound. Example: Molecular formula of benzene is C6H6
whichshow6atomsofcarbonand6atomsofhydrogen.

Compound
Empericalformula
Molecularformula

Hydrogenperoxide
HO
H2O2

Glucose
CH2O
C6H12O6

Benzene
CH
C6H6

Napthalene
C5H4
C10H8

Ethene
CH2
C2H4

Ethane
CH3
C2H6

Relationbetweenempericalformulaandmolecularformula:
Empericalformulaandmolecularformulaarerelatedby
Molecularformula=(empericalformula)n

Wherenissimplewholenumberandisgivenby,

Molecularmass
n=
Empericalformulamass

Example:Molecularmassofacetyleneis26,
EmpericalformulaofacetyleneisCH,
empericalformulamassis13.
26
n= =2
13
molecularformulaofacetylene=(CH)2=C2H2

Hydrocarbons:

Hydrocarbonsarecompoundsmadeupofcarbonandhydrogen.Hydrocarbons
are regarded as chief or parent compounds, hence modern definition of organic
chemistry is, the chemistry of the hydrocarbons and their derivatives. Other
compoundsofcarbonareconsideredasderivativesofhydrocarbonsthatareobtained
byreplacingoneormorehydrogenatomswithatomsofelementslikeoxygennitrogen,
halogenetc.

Classification:

Hydrocarbonsareclassifiedas
1. Saturatedhydrocarbons
2. Unsaturatedhydrocarbons

Saturated hydrocarbons contain carboncarbon single bond. Example: alkanes,

cycloalkanes.

Unsaturatedhydrocarboncontaincarboncarbondoublebondorcarboncarbon
triplebondorboth.Example:alkenes,alkynes

Alkanes are compounds containing different carbon atoms with carboncarbon

singlebondtoformopenchainofcarbonatoms.Example:methane,ethane,etc.

Alkenes are compounds containing carboncarbon double bond in the open

chainofcarbonatoms.Example:ethene,propene,etc.

Alkynes are compounds containing carbon carbon triple bond in the open
chainofcarbonatomsaretermedasalkynes.Example:ethyne,propyne,etc.

Structuralrepresentationofhydrocarbons:

Structuralformulaisrepresentedbyshowing,covalentbondbybetween
twoatoms.Hence,
singlebondisrepresentedby,
doublebondisrepresentedby=,
triplebondisrepresentedby.
Sincecarbonistetravalent,inthestructuralformula,alwayscarbonhasfourbonds.

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Examples:

1.Alkanes

Name

Methane

Molecular
formula
CH4

Structuralformula

Ethane

C2H6

HH
HCCH
HH

Propane

C3H8

HHH
HCCCH
HHH

2.Alkenes

Ethene

C2H4

HH
HC=CH

H
HCH
H

HHH
HCC=CH
H
HHHH
HC=CCCH
HH

Propene

C3H6

Butene

C4H8

3.Alkynes

Ethyne

C2H2

HCCH

Propyne

C3H4

Butyne

C4H6

H
HCCCH
H
HH
HCCCCH
HH

Substitutionreaction:

Reactionsinwhichoneormorehydrogenatomsofhydrocarbonsaresubstituted
orreplacedbysomeotheratomorgroupofatoms.

Example:HalogenationofalkanesItinvolvesreplacementofhydrogenatomsofalkane
byhalogenatom.

Chlorination:Methanewhentreatedwithchlorineinpresenceofdiffusedlight
forms chloromethane, dichloromethane, trichloromethane, tetrachloromethane by
replacingone,two,threeandfourhydrogenatomsofmethane.

CH4+Cl2diffusedlightCH3Cl+HCl
(methane)

(chloromethane)
CH3Cl+Cl2diffusedlightCH2Cl2+HCl

(dichloromethane)
CH2Cl2+Cl2diffusedlightCHCl3+HCl

(trichloromethane
orchloroform)
CHCl3+Cl2diffusedlightCCl4+HCl
(tetrachloromethane
orcarbontetrachloride)

AdditionReactions:

Alkenes and alkynes contain double and triple bonds respectively and are rich
source of electrons. Hence are more reactive and undergo addition reactions to form
saturatedproducts.

Example:

1. Addition of hydrogen: Ethene undergo addition reaction with hydrogen, when

heatedinpresenceofnickelcatalysttoformethane
HHHH
HC=CH+H2NiHCCH
etheneHHethane

2. Addition of bromine: Ethene undergo addition reaction with bromine in carbon

tetrachloridetoform1,2dibromoethane.
HHHH
HC=CH+Br2CCl4HC2C1H
ethene
BrBr

1,2dibromoethane

Nomenclature(Elementaryidea):
IUPACsystemofnamingorganiccompounds

A proper name is assigned to a particular organic compound on the basis of

IUPACsystem(internationalunionofpureandappliedchemistry)
In IUPAC system, name of organic compound consists of three parts 1) root word
2)suffix3)prefix.

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1. Root word denotes number of carbon atoms in the parent chain. Root word for
carbonchaincontainingdifferentnumberofcarbonatomsareasgivenbelow.

No. of carbon Root No. of carbon Rootword

atomsinchain word atomsinchain
1
meth 6
hex
2

eth

prop 8

oct

but

non

pent 10

hept

dec

2. Suffix:Itisthewordlinkedtotherootwordattheend.Itisoftwotypes

a) primarysuffix:Itindicatesnatureoflinkageincarbonatoms.Example:For
carbonatomslinkedbyasinglecovalentbond,suffix:ane,forcarbonatoms
linked by double bond, suffix: ene, for carbon atoms linked by triple bond,
suffix:yne.

b) Secondarysuffixindicatespresenceoffunctionalgroupandsecondarysuffix
word is added by replacing e of ane, ene and yne of primary suffix word.
(Note:eisretainedifsecondarysuffixbeginswithaconsonant)

Class of organic Functionalgroup SecondarySuffix

compound
Alcohols
OH
ol

Aldehydes

CHO

al

Ketones

C=O

one

Carboxylicacids

COOH

oicacid

Esters

COOR

alkyl..oate

Nitriles

CN

nitrile

Amines

NH2

amine

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3. Prefix:Itreferstosidechainorsubstituentandisplacedbeforetherootword.

Substituent
Prefix
Substituent Prefix
F
Fluoro
No
nitroso
Cl

Chloro

OCH3

methoxy

Br

Bromo

OC2H5

ethoxy

Iodo

CH3

Methyl

NO2

Nitro

CH3CH2

Ethyl

HenceIUPACnamesofsomealkane,alkeneandalkynesareasfollows.

Commonname Compound
Rootword
IUPACname

H
Rootword:meth
Meth+ane=methane
1)Methane
HCH
Primarysuffix:ane
H

HH
2)Ethane
Rootword:eth
Eth+ane=ethane
HCCH
PrimarySuffix:ane
HH

HHH
3)Propane
Rootword:prop
Prop+ane=propane
HCCCH
PrimarySuffix:ane
HHH

HH
4)Ethylene
Rootword:eth
eth+ene=ethene
HC=CH
PrimarySuffix:ene

HHH
5)Propylene
Rootword:prop
Prop+ene=propene
HCC=CH
PrimarySuffix:ene
H

but+ene=but1ene
Rootword:but
6)butylene HHHH
HC1=C2C3C4H
PrimarySuffix:ene
HH
(doublebondat1stcarbon)
HCCH
7)Acetylene
Rootword:eth
eth+yne=ethyne

PrimarySuffix:yne

8)Methylacetylene H
HCCCH
H
9)Ethylacetylene

HH
HC4C3C2C1
HHH

Rootword:prop
PrimarySuffix:yne

Rootword:but
PrimarySuffix:yne

Prop+yne=propyne

but+yne=but1yne

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IUPACnamesofcompoundswithFunctionalgroups

CommonName
Compound
Alcohols:

HH
1)Ethylalcohol
HCCOH
HH

IUPACname

Ethanol

2)nbutylalcohol

Aldehydes:
3)Formaldehyde

HHHH
HCCCCOH
HHHH

H
HC=O

Butanol

Methanal

4)Acetaldehyde
Ketones:
5)Dimethylketone

HH
HCC=O

HO H
HCCCH
HH

Ethanal

Propanone

6)ethylmethylketone

Carboxylicacids:
7)Formicacid
8)Aceticacid

HOHH
HCCCCH
HHH

O
HCOH

HO
HCCOH
H

Butan2one

Methanoicacid
Ethanoicacid

Esters:
9)Ethylacetate

HOH H
HCCOCCH
HHH

Ethylethanoate

10)Methylacetate

H OH
HCCOCH
HH

Methylethanoate

Nitriles:
11)Methylcyanide

H
HCCN
H

Ethanenitrile

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HH
HCCCN
HH

12)Ethylcyanide

Propanenitrile

Amines:
13)Methylamine

HH
HCNH
H

Methanamine

HHH
HCCNH
HH

14)Ethylamine

Ethanamine

IUPACnamesofcompoundswithsubstituent.

CommonName
Compound
HHH
1)Isobutane

IUPACname
2methylpropane

2)Ethylchloride

Chloroethane

HC1C2C3H
HH
HCH
H

HH
HCCC l
HH

3)Isopropyliodide

H HH
HC1C2C3H
HIH

2iodopropane

4)Secbutylbromide

HH HH
HCCCCH
HBrHH

2bromobutane

5)Ethylmethylether

HHH
HCOCCH
HHH

Note:Nomenclatureisdealtindetailin11thstandard.

Methoxyethane

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EXERCISES

1) Explaintetravalencyofcarbon
2) Whatiscatenation?
3) Carbonformslargenumberofcompounds.Justify.
4) Defineorganicchemistry
5) Explainthescopeoforganicchemistry
6) Whatarefunctionalgroups?
7) Mentionthefunctionalgroupofalcoholandaldehye.
8) Whatishomologousseries?Explainwithexample.
9) WritemolecularformulaoftwosuccessivehomologuesofC3H8
10) Whatisgeneralformulaofalkynes
11) Whatisempiricalformula?Giveexample.
12) Whatismolecularformula?Giveexample.
13) Writetherelationbetweenempiricalformulamassandmolecularformulamass
14) Whatarehydrocarbons?
15) Classifythefollowingintosaturatedandunsaturatedhydrocarbons
a. Ethane
c. Ethene

b.Butane
d.Propye

16) Whatarealkanes?Giveexample.
17) Whatareakenes?Givetwoexamples
18) Whatarethecompoundscontainingcarboncarbontriplebondintheopen
chainofcarbonatomscalledas?
19) Writethestructuralformulaof
a. propane

b.Butene

c.Ethyne

20) Whatissubstitutionreaction?Explainchlorinationofmethane
21) Howmanysubstitutionproductsareformedfromthereactionbetweenethane
andchlorine
22) Whyarealkeneandakynesmorereactivecomparedtoalkanes
23) Explainadditionofhydrogentoethene
24) Writethenameandstructuralformulaofproductformedbyadditionof
brominetoethene
25) WhatdoestherootwordofIUPACnameoforganiccompoundindicate?

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26) Whatistherootwordgivenforthechainofsixcarbonatoms?
27) Whatisaprimarysuffix
28) Whatistheprimarysuffixgivenforcarbonatomslinkedby
a. Doublebond

b.Triplebond

29) Whatissignificanceofsecondarysuffixinthenomenclatureoforganic
compounds?
30) Whatarethesecondarysuffixforthefunctionalgroups
a. Aldehyde

b.Ketone

c.Carboxylicacid
31) WhatdoestheprefixpartoftheIUPACnameoforganiccompoundsrepresent?

32) Whataretheprefixesusedfor
a. NO2

b.CH3

33) Writethestructuralformulaforthefollowing
a. Propene

b.1butanol
c.Chloroethane

34) WritetheIUPACnameofthefollowing
a.
b.
HO

HHH

HCCOH
HCCCH

H
HIH

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Preparedby:

ShobhaGorbal

HeadoftheDept.ofChemistry,

VidyaMandirIndependentPUCollege,

11thCross,Malleshwaram,Bangalore