1.7 - Introduction To Organic Chemsitry (Alkanes + Alkenes) - Notes To Students

10/3/2011
OrganicChemistryI
By: ChemistryDepartment, INTEC
ChapterOutline
Introduction CommonTerminologyinOrganicChemistry Common Terminology in Organic Chemistry SystematicNomenclature Isomerism Alkanes Alkenes Halogenoalkanes Alcohols Bondingandreactivity Quantitativeorganicchemistry Appliedorganicchemistry
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Introduction
Organiccompoundsconsistofoneormore carbonatomsandcontainfunctionalgroups. b t d t i f ti l Thefunctionalgroupdeterminesthechemical propertiesofthecompound. Examplesoforganiccompounds:alkanes, alkenes,alcohols,carboxylicacids alkenes alcohols carboxylic acids
CommonTerminologyinOrganicChemistry
Homologous series: a series of compounds with Homologousseries: aseriesofcompoundswith thesamefunctionalgroupandthesamegeneral formula,whereonememberdiffersfromthe nextbyCH2 Empiricalformula: representsthesimplestwhole numberratioofatomsinamolecule b i f i l l Molecularformula: representstheactual numberofatomsinamolecule
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Contd
CommonTerminologyinOrganic Chemistry
Structural formula: represents the arrangement of Structuralformula: representsthearrangementof atomsinamolecule;usuallywritteninexpanded, condensedorskeletalform
Expandedformula
Condensedformula
Skeletalformula
Contd
Homolyticfission: whenabondbreakswithone electrongoingtoeachatom(formingradicals) Heterolyticfission: whenabondbreakswiththe twoelectronsgoingtoonlyoneatom Freeradical: aspeciesthathasasingleunpaired electron
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Contd
Nucleophile: aspecieswhichseeksoutpositive centres,andmusthavealonepairofelectrons toformanewcovalentbond Electrophile: a species which seeks out negative Electrophile:aspecieswhichseeksoutnegative centres,andacceptsalonepairofelectronsto formanewcovalentbond
SystematicNomenclature: Alkanes
From the structural formula of compound find the Fromthestructuralformulaofcompound,findthe longestcontinuous carbonchain.Assignnamefor thischainusingcorrespondingprefixandsuffix ane.
Number of carbon atoms Prefix
Meth-
Eth-
Prop-
But-
Pent- Hex- Hept-
Oct-
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Contd
Locate alkyl groups that are not part of the Locatealkylgroupsthatarenotpartofthe continuouschainandnamethemaccordingtothe numberofcarbonatomspresent,withsuffixyl. Thepositionofthebranchingalkylgroupis numberedfromtheparentchainsothatitsposition isatthelowestpossiblenumber. is at the lowest possible number. Numbersareseparatedfromeachotherbycommas andfromwordsbyhyphens.
Contd
If an alkane compound contains two or more Ifanalkanecompoundcontainstwoormore identicalbranches,thefollowingprefixesareused:
Number of branches Prefix
2 Di-
3 Tri-
4 Tetra-
Ifanalkanecompoundhastwoormoredifferent branchingalkylgroups,theyareplacedin alphabeticalorderofthename.
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Contd
If an alkane compound has other substituents such Ifanalkanecompoundhasothersubstituentssuch ashalogen,itisaddedbeforethenameofthe alkaneandnumberedatthelowestposition. Iftherearetwoormoreofasimilarsubstituentsare attachedtothealkane,theprefixdi,tri ortetra is attached to the alkane the prefix di tri or tetra is addedaccordingly.
Contd
Example 1: Example1:
4321
Name:2methylbutane 2 Example 2: Example2:

7654321
Name:4ethyl2,3dimethylheptane 4 ethyl2,3
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Contd
8 7 4 2 1 3 5 6
Name:2,6dimethyloctane 2,6
Contd
Name:1bromopropane 1
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Contd
Name the following organic compound using Namethefollowingorganiccompoundusing systematicnames: 1. CH3CH2CH2CH2CH2CH3 2.
3.
Contd
SystematicNomenclature: Alkenes
Thelongestcarbonchainforalkenesmust containatleastonecarbonwithdoublebond(s). contain at least one carbon with double bond(s) Foralkenes,startingfrom4carbonatomsthe compoundhavetobenumberedaccordingtothe positionofdoublebond(s)inthecompound. Thenumberingshouldhavethedoublebond(s) atthelowestpossiblenumbercombination.
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Contd
Theprefixissimilarwithalkanes,butthe suffixchangestoene. ffi h t Iftherearemorethanonedoublebond,the prefixdi,tri ortetra isaddedaccordingly.
Contd
Example1:
1234
Name:1,3butadiene/buta1,3diene 1,3butadiene/buta1,3
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Contd
Example2:
6 2 1 3 4 5
Name:2methyl2hexene/2methylhex2ene 2 methyl hexene/2methylhex
Contd
Name the following compound using systematic Namethefollowingcompoundusingsystematic names.
1.
2.
3.
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Contd
SystematicNomenclature: Alcohols
Foralcohols,thelongestcarbonchainshould o a co o s, e o ges ca bo c a s ou d consistofatleastonehydroxyl(OH)group(s). Foralcohols,thesuffixisol. Startingfrom3carbonatoms,thenumberingis donesothatthehydroxylgroupisatthelowest possibleposition. possible position. Iftherearetwoormoreofhydroxylgroups,prefix di,tri ortetra isaddedaccordingly.
Contd
Example1:
Name:ethanol Name:ethanol
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Contd
Example2:
3 2 1
Name:2propanol/propan2ol Name:2 propanol/propan
Contd
Example3:
4 3 2 1
Name:2,3butandiol/butan2,3diol Name:2,3butandiol/butan2,3
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Contd
Namethefollowingcompoundsusing systematicnames:
1. 2. 2. 3.
Contd
SystematicNomenclature: OtherFunctionalGroups
For other functional groups, the rules for naming Forotherfunctionalgroups,therulesfornaming themaresimilarwithalcohols. However,foraldehydesandcarboxylicacids,the numberingstartswiththecarbonyl/carboxylgroup. Thecarbonyl/carboxylgrouparenotusuallygiven number,unlessiftherearemorethanoneofthe samefunctionalgroups.Otherfunctionalgroup(s) same functional groups Other functional group(s) attachedtoaldehydesorcarboxylicacidsare numbered,withthefirstcarbonisthe carbonyl/carboxylgroups.
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Contd
Substance Functional Group Aldehyde Ketone Carboxyli c Acid
Suffix
-al
-one
-oic acid
Contd
Example1:
Name:butanal butanal
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Contd
Example2:
5
4 3 2 1
Name:2methylpentanal 2
Contd
Example3:
4 2 5 3 1
Name:2pentanone/pentan2one 2 pentanone/pentan
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Contd
Example4:
Name:ethanoicacid ethanoicacid
Contd
Example5:
3 2 1
Name:2chloropropanoicacid 2
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Contd
Namethefollowingcompoundsusingsystematic names:
1.
2.
Contd
Namethefollowingcompoundsusingsystematic names:
3.
4.
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Isomerism
Structuralisomers: compoundsthathave similarmolecularformulabutdifferent i il l l f l b t diff t structuralformula. Structuralisomersmayhave:
Differentcarbonchains(straightorbranched) Different position of functional group in the Differentpositionoffunctionalgroupinthe carbonchain Differentfunctionalgroups
Contd
Isomerism
Example of structural isomers (different carbon Exampleofstructuralisomers(differentcarbon chains):
pentane
2,2 2,2dimethylpropane
2methylbutane
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Contd
Isomerism
Exampleofstructuralisomers(differentposition offunctionalgroup):
1propanol
2propanol
Contd
Isomerism
Exampleofstructuralisomers(different a p e o st uctu a so e s (d e e t functionalgroups): Molecularformula:C3H6O2
Ethylmethanoate y
Propanoicacid P i id
Methylethanoate
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Contd
Isomerism
Geometricisomers: onlyoccursifthereisa doublebondinthemolecule,andeachcarbon d bl b d i th l l d h b hasdifferentatomsorgroupsattachedtoit. Geometricalisomershaverestrictedrotation aboutthedoublebond.
Contd
Isomerism
Exampleofgeometricisomers:
cis2butene
trans2butene
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Contd
Isomerism
Opticalisomers: existincompoundswhere4different groupsareattachedtoasinglecarbonatom. Thecarbonischiral(assymetrical). Apairoftheseisomersarecalledenantiomers andtheir enantiomers mirrorimageisnotsuperimposable (ornon superimposablemirrorimage) Amixturecontainingequalamountofopticalisomersis A mixture containing equal amount of optical isomers is calledaracemicmixture racemicmixture.
Contd
Isomerism
OpticalIsomers
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Alkanes
Generalformula:CnH2n+2 1Combustionreaction:
Generalreaction: CnH2n+2 +[(3n+1)/2]O2 Example: CH4 + nCO2+(n+1)H2O
2O2
CO2
2H2O
Contd
Alkanes
2SubstitutionreactioninpresenceofUV light(Xhalogen,usuallyCl2 orBr2):
Generalreaction: CnH2n+2 + X2 CnH2n+1X+ X2
UVlight
CnH2n+1X +HX CnH2nX2 +HX
UVlight
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SubstitutionReactionofAlkanes
inpresenceofUVlight(Xhalogen,usuallyCl2 orBr2) E B ):Example: l
CH4 CH3Cl + + Cl2 Cl2
UVlight
CH3Cl CH2Cl2 Cl
+HCl +HCl HCl
UVlight
Contd
Alkanes
Reactionmechanism:Homolytic,freeradical Reaction mechanism: Homolytic free radical Homolytic,freeradical substitution 1. Initiationstep:Homolyticfissiontofreeradicals
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Contd
Alkanes
Reactionmechanism:Homolytic,freeradical Reaction mechanism: Homolytic free radical Homolytic,freeradical substitution 2. Propagationstep
Contd
Alkanes
Reactionmechanism:Homolytic,freeradical Reaction mechanism: Homolytic free radical Homolytic,freeradical substitution
2. Propagationstep
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Contd
Alkanes
Reactionmechanism:Homolytic,freeradical Homolytic,freeradical substitution
3. Terminationstep
Contd
Alkanes
Reactionmechanism:Homolytic,freeradical Homolytic,freeradical substitution
3. Terminationstep
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Contd
Alkanes
Reactionmechanism:Homolytic,freeradical Homolytic,freeradical addition
3. Terminationstep
Alkenes
Generalformula:CnH2n 3Additionreaction:
Withhydrogengas,at150C:
Ni/Pt/Pd
CnH2n C3H6
+ + +
H2
Ni/Pt/Pd
CnH2n+2 C3H8
H2
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Alkenes
4Additionreaction:
With halogens, at room temperature (X2=Cl2 or Withhalogens,atroomtemperature(X Cl or Br2): CnH2n + X2 CnH2nX2 CH3CHBrCH2Br
CH3CH=CH2 +Br2
Additionreactionofalkene
Thechangeofcolourforbromine,fromredbrown tocolourlessisatestforC=Cgroupina to colourless is a test for C=C group in a compound.Forthetest,bromineisdissolvedin CCl4.
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Contd
Alkenes
5Additionreaction
Withhydrogenhalides(HI/HBr),atroomtemperature: CnH2n + HX CnH2n+1X
CH3CH=CHCH3
+HBr
CH3CH2CHBrCH3
Additionreactionofalkene
Withunsymmetricalalkenes,hydrogenatomgoes tothecarbonthathasmorehydrogenatoms to the carbon that has more hydrogen atoms bondeddirectlytoit(Markovnikoffsrule).
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Contd
Alkenes Mechanism
Heterolytic,electrophilic additionreaction 1. Protonationtocarbocation:electrophilicaddition
2. Nucleophilicattack 2 N l hili tt k
2 cation morestable
1 cation
Contd
Alkenes
Addition reaction Additionreaction
..\abaddition.avi \ b dditi i
Minor
Major
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Contd
Alkenes
6Oxidationreaction Oxidizing agent: Potassium permanganate Oxidizingagent:Potassiumpermanganate (KMnO4)inalkaline/acidiccondition,atroom temperature
CnH2n +[O]+H2O CnH2n(OH)2 CH3CH=CHCH3 +[O] +H2O CH3CH(OH)CH(OH)CH3 Potassiumpermanganatewillbereducedto manganesedioxide,whichisseenasbrown precipitate.
Contd
Alkenes
7Polymerisationreaction
.MechanismAnimated\polymerization.avi
Conditions:eitherhighpressureandtemperature (2000atm,250C) ormoderatepressureand temperaturewithcatalystaddition(10atm, 50C,catalyst:titanium(IV)chloride+triethyl aluminium) Additi Additionreaction ti nCnH2n

(CnH2n)n
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10/3/2011

Number of carbon atoms Prefix

Pent- Hex- Hept-

Ifanalkanecompoundhastwoormoredifferent branchingalkylgroups,theyareplacedin alphabeticalorderofthename.

Name:2methylbutane 2 Example 2: Example2:

Name:2methyl2hexene/2methylhex2ene 2 methyl hexene/2methylhex

Name:2propanol/propan2ol Name:2 propanol/propan

CnH2n+1X +HX CnH2nX2 +HX

+HCl +HCl HCl

Conditions:eitherhighpressureandtemperature (2000atm,250C) ormoderatepressureand temperaturewithcatalystaddition(10atm, 50C,catalyst:titanium(IV)chloride+triethyl aluminium) Additi Additionreaction ti nCnH2n

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