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OrganicChemistry 2010-11-24 Setby:MrFGray StStithiansCollege

OrganicChemistry

2010-11-24

Setby:MrFGray

StStithiansCollege

Organicmolecules hydrogen. compoundsthatconsistprimarilyofcarbonand Organicchemistryisdefinedasthechemistryof

Organicmolecules

hydrogen.

compoundsthatconsistprimarilyofcarbonand

Organicchemistryisdefinedasthechemistryof

Atomsofnitrogen,oxygen,halogens,sulphurand

molecules.

phosphorusarealsosometimespartoforganic

2010-11-24

StStithiansCollege

Thechemistryofcarbon withatomsofothernon-metals. covalent bondswithothercarbonatomsandalso Carbonatomshavetheabilitytoform

Thechemistryofcarbon

withatomsofothernon-metals.

covalentbondswithothercarbonatomsandalso

Carbonatomshavetheabilitytoformstrong

bethousandsofatomslong

formchainsorringstructures.Thesechainscan

Carbonatomsbondwithothercarbonatomsto

.

withthemselvestoformchainorringstructures.

Catenation–theabilityofcarbonatomstobond

2010-11-24

StStithiansCollege

Importantfeaturesofcarbon twoexamples. Allotropesofcarbonexist.Graphiteanddiamondare Diamond Diamond Diamond Diamond

Importantfeaturesofcarbon

twoexamples.

Allotropesofcarbonexist.Graphiteanddiamondare

Diamond

Diamond

Diamond

Diamond

2010-11-24
2010-11-24

Graphite

Graphite

Graphite

Graphite

Diamond Diamond Diamond Diamond 2010-11-24 Graphite Graphite Graphite Graphite
Diamond Diamond Diamond Diamond 2010-11-24 Graphite Graphite Graphite Graphite
.Thismeansitcanform4 4 4 of4 4 of of valencyof valency Carbonhasavalency valency
.Thismeansitcanform4
4
4
of4
4
of
of
valencyof
valency
Carbonhasavalency
valency

outermostenergylevel).

bondsandhas4valenceelectrons(4electronsinthe

otherelements.

Carbonwillformamaximum

maximumofFOURbondswith

maximum

maximum

2010-11-24

Acarbonatomintheground
Acarbonatomintheground

state

2p

2p

2p

2p

2s

2s

2s

2s

2s 2s 2s 2s
2s 2s 2s 2s

1s

1s

1s

1s

1s 1s 1s 1s
1s 1s 1s 1s

2010-11-24

2p 2p 2p 2s 2s 2s 2s 1s 1s 1s 1s 2010-11-24 Electronconfiguration:1s ²2s 2s ²
2p 2p 2p 2s 2s 2s 2s 1s 1s 1s 1s 2010-11-24 Electronconfiguration:1s ²2s 2s ²
2p 2p 2p 2s 2s 2s 2s 1s 1s 1s 1s 2010-11-24 Electronconfiguration:1s ²2s 2s ²

Electronconfiguration:1s

²2s

2s

²

²

²

2s

2s

²

²

²

²

2p

2p

2p

2p

²

²

²

²

” excited Acarbonatominthe“
excited
Acarbonatominthe“

state

2p

2p

2p

2p

” excited Acarbonatominthe“ state 2p 2p 2p 2p 2s 2s 2s 2s 1s 1s 1s 1s
” excited Acarbonatominthe“ state 2p 2p 2p 2p 2s 2s 2s 2s 1s 1s 1s 1s

2s

2s

2s

2s

1s

1s

1s

1s

state 2p 2p 2p 2p 2s 2s 2s 2s 1s 1s 1s 1s Electronconfiguration:1s 2p 2p
state 2p 2p 2p 2p 2s 2s 2s 2s 1s 1s 1s 1s Electronconfiguration:1s 2p 2p
state 2p 2p 2p 2p 2s 2s 2s 2s 1s 1s 1s 1s Electronconfiguration:1s 2p 2p

Electronconfiguration:1s

2p 2p 2p 2p ¹ ¹ ¹ ¹ 2s 2s 2s ²2s ² ² ²
2p
2p
2p
2p
¹ ¹
¹
¹
2s
2s
2s
²2s
²
² ²
C
C
C
C

³

³

³

³

¹ ¹ 2s 2s 2s ²2s ² ² ² C C C C ³ ³ ³

Structure

Couper

Intheexcitedstate

,valenceelectronsareunpaired

i.e.the2selectronmovestohigher2porbital.

2010-11-24

Thehydrocarbons carbon and hydrogenatomsonly Hydrocarbons –organicmoleculesthataremadeupof . H H H C C C HH C

Thehydrocarbons

carbonandhydrogenatomsonly

Hydrocarbons–organicmoleculesthataremadeupof

.

H

H

H

Hydrocarbons –organicmoleculesthataremadeupof . H H H C C C HH C C C C C C

C

C

C

–organicmoleculesthataremadeupof . H H H C C C HH C C C C C C C

HHC

C

C

C

C

C

C

C

AlkanesHC

Alkanes

Alkanes

Alkanes

C C C HH C C C C C C C C Alkanes H C Alkanes

H

H

H

Saturatedhydrocarbons

Saturated

hydrocarbons

hydrocarbons

Saturated

Saturated

hydrocarbons–hydrocarbonwhichhasall

H

singularlyoccupied.

singularly

singularly

fourbondstothecarbonatomsinitsstructure

singularly

2010-11-24

TheHydrocarbons atomswithinitsstructure. have multiplebonds (doubleortriple)tothecarbon Unsaturatedhydrocarbons

TheHydrocarbons

atomswithinitsstructure.

havemultiplebonds(doubleortriple)tothecarbon

Unsaturatedhydrocarbons–organicmoleculeswhich

Alkenes

Alkenes

Alkenes

Alkenes

Alkynes

Alkynes

Alkynes

Alkynes

2010-11-24

C C C C C C HC C H H
C
C
C
C
C
C
HC
C
H
H

H

HC

CC

C

C

Alkenes Alkenes Alkenes Alkynes Alkynes Alkynes Alkynes 2010-11-24 C C C C C C HC C

CH

C

C

Homologousseries Homologousseries –afamilyoforganicmolecules obeythe samegeneralformula whichareidentifiedbythe

Homologousseries

Homologousseries–afamilyoforganicmolecules

obeythesamegeneralformula

whichareidentifiedbythesamefunctionalgroupand

.

2010-11-24

Functionalgroup Functionalgroup –a bond , atom or groupofatoms in theorganicmoleculewhichidentifiestowhich

Functionalgroup

Functionalgroup–abond

,atomorgroupofatomsin

theorganicmoleculewhichidentifiestowhich

responsibleforthechemicalpropertiesofthatmolecule.

homologousseriesthatmoleculebelongsandis

Functionalgroup

Functional

group

group

Functional

Functional

sof

hydrocarbons:

ofhydrocarbons:

of

of

hydrocarbons:

hydrocarbons:

groups

s

s

AlkanesAlkenes

Alkanes

Alkanes

Alkanes

Alkenes

Alkenes

AlkenesAlkynes

Alkynes

Alkynes

Alkynes

C C C CC C C C C C C CC C C C C
C
C
C
CC
C
C
C
C
C
C
CC
C
C
C
C
C
CC
C
C
C
C

2010-11-24

Namingthehydrocarbons ofcarbonatoms fromtheendnearest Numberthe longestcontinuouschain theprefixofthename. the

Namingthehydrocarbons

ofcarbonatomsfromtheendnearest

Numberthelongestcontinuouschain

theprefixofthename.

thefunctionalgroup

.Thisdetermines

Thefunctional

functional

functional

functionalgroup

groupdetermines

group group

thesuffix:

Alkanes(singlebonds)endin-

ane

.

Alkenes(doublebond)endin-

ene

.

Alkynes(triplebond)endin–

yne

yne

yne

yne

.

2010-11-24

No

Noof

No

No

ofC

C

of

of

C

C

atoms

atoms

atoms

atoms

Prefix

Prefix

Prefix

Prefix

1

Meth

2

eth-

3

prop-

4

but-

5

pent-

6

hex-

7

hept-

8

oct-

Typesofformulae molecule. moleculeshowing allthebonds toalltheatomsinthe Structuralformula –thestructureofanorganic H H

Typesofformulae

molecule.

moleculeshowingallthebondstoalltheatomsinthe

Structuralformula–thestructureofanorganic

H H H

H

ane But H H H H C C C C C C C C C
ane
But
H
H H
H
C
C
C
C
C
C
C
C
C
C
C
C
C
C
HC
C
4
3
2
1

2010-11-24

H

H H C C C C C C C C C C C C C
H
H
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
HC
34
2
1
H
H
H H

But-2-ene

H

Typesofformulae bonds inthemolecule. anorganicmoleculethatonlyshowsthe mostimportant Semi(condensed)structuralformula

Typesofformulae

bondsinthemolecule.

anorganicmoleculethatonlyshowsthemostimportant

Semi(condensed)structuralformula–thestructureof

C

C

C

C

HC

C

C

C

HC

C

C

C

HC

C

C

C

322

But

ane

C

C

C

C

2010-11-24

H

3

C

C

C

C

HC

C

C

CC

C

C

HH

CC

C

C

C

3

But-2-ene

HC

3

CC

C

C

C

C

But ane C C C C 2010-11-24 H 3 C C C C H C C

CC

C

C

C

H

3

But-2-yne

H

3

Typesofformulae Molecularformula –onlyindicatesthe number and typesofatoms presentintheorganiccompound. C3H8 C3H8

Typesofformulae

Molecularformula–onlyindicatesthenumberand

typesofatomspresentintheorganiccompound.

C3H8

C3H8

C3H8

C3H8

C5H10

C5H10

C5H10

C5H10

C3H4

C3H4

C3H4

C3H4

Generalformula:

formula:

formula:

formula:

Drawthestructuralformulaeforthesemoleculesandnamethem.

Alkanes

Alkanes

Alkanes

Alkanes

CnH2n+2

CnH2n+2

CnH2n+2

CnH2n+2

2010-11-24

Alkenes

Alkenes

Alkenes

Alkenes

CnH2n

CnH2n

CnH2n

CnH2n

Alkynes

Alkynes

Alkynes

Alkynes

CnH2n-

- -

CnH2n

CnH2n

CnH2n

-2

2

2

2

Alkanes bonds betweenthecarbonatoms. and hydrogen atoms.Theyare hydrocarbons with single Alkanesare non-polar

Alkanes

bondsbetweenthecarbonatoms.

andhydrogenatoms.Theyarehydrocarbonswithsingle

Alkanesarenon-polarmoleculescontainingonlycarbon

unreactive

unreactive

Theyaresaturated

saturated

unreactive

unreactive

saturated

saturated

.

.Thismakesthealkanesquite

Asthesize

size size

sizeofthemolecule

moleculeincreases

increases

molecule

molecule

increases

increases

,thestrength

ofthevan

van van

vander

derWaal

der

Waal

Waal

Waal

der

sforces

s

s

s

forcesincreases

increases

increases

forces

forces

increaseshence

than12carbonatoms)aresolidsatroomtemperature.

gasesfollowedbyliquids.Thelargermolecules(more

boilingpoints

boiling

boiling

boiling

points points

pointsincrease

increase

increase

increase

.Methanetobutaneare

2010-11-24

Namethesealkanesandwritedownthemolecularformula foreachmolecule. ethane methane propane CH4 CH4 CH4 CH4 C2H6 C2H6 C2H6

Namethesealkanesandwritedownthemolecularformula

foreachmolecule.

ethane methane propane
ethane
methane
propane
foreachmolecule. ethane methane propane CH4 CH4 CH4 CH4 C2H6 C2H6 C2H6 C2H6 C3H8 C3H8 C3H8 C3H8
foreachmolecule. ethane methane propane CH4 CH4 CH4 CH4 C2H6 C2H6 C2H6 C2H6 C3H8 C3H8 C3H8 C3H8

CH4

CH4

CH4

CH4

C2H6

C2H6

C2H6

C2H6

C3H8

C3H8

C3H8

C3H8

2010-11-24

Alkenes unsaturatedhydrocarbons betweentwocarbonatoms.Thismakesthem The alkenes containatleastone double bond .

Alkenes

unsaturatedhydrocarbons

betweentwocarbonatoms.Thismakesthem

Thealkenescontainatleastonedoublebond

.

Thesimplestalkeneisethene(ethylene).

(polyethylene).

andisusedtomaketheplasticpolythene

Etheneisanimportantcommercialorganicchemical

2010-11-24

CH3 CH3 –CH3 CH3 – CH2– – CH2 –CH2 CH2 – CH– – CH CH
CH3 CH3 –CH3 CH3 – CH2– – CH2 –CH2 CH2 – CH– – CH CH
CH3
CH3
–CH3
CH3
CH2–
CH2
–CH2
CH2
CH–
CH
CH
=CH
=
H2C=
=
H2C
H2C
H2C
4
4
4
34
3 3
23
2 2
12
1 1
1

2010-11-24

But-

-

-

But

But

But

-1

1-

1

1

-ene

-

-

ene ene ene

Alkynes massiveamountofheat.(30000C).Itisusedinthe Thecombustionofethyneandoxygenreleasesa

Alkynes

massiveamountofheat.(30000C).Itisusedinthe

Thecombustionofethyneandoxygenreleasesa

Thesimplestalkyneisethyne(acetylene).

Thismakesthemunsaturatedhydrocarbons

twocarbonatoms.

Thealkynescontainatleastonetriplebondbetween

.

oxyacetylenetorchtocutmetals.

2010-11-24

CH3 CH3 –CH3 CH3 – CH2– – CH2 CH2 –CH2 – C– – C C
CH3 CH3 –CH3 CH3 – CH2– – CH2 CH2 –CH2 – C– – C C
CH3
CH3
–CH3
CH3
CH2–
CH2
CH2
–CH2
C–
C
C
C
HC
HC
HC
HC
4
4
34
4
3
23
3
2 2
12
1
1 1

2010-11-24

But-1-yne

But-1-yne

But-1-yne

But-1-yne

Branchedorganicmolecules organicmolecule. attached tothelongestcontinuouscarbonchaininan Alkylsubstituent –a

Branchedorganicmolecules

organicmolecule.

attachedtothelongestcontinuouscarbonchaininan

Alkylsubstituent–acarbonbased“

sidechain

whichis

Alkyl

Alkylgroup

group

group

Alkyl

Alkyl

groupstructure

structure

structure

structure

Alkyl

Alkylname

name name

name

Alkyl

Alkyl

CH3-

-

CH3

CH3

CH3

-

-

methyl

CH3-CH2-

CH3-CH2-

CH3-CH2-

CH3-CH2-

ethyl

CH3-CH2-CH2-

CH3-CH2-CH2-

CH3-CH2-CH2-

CH3-CH2-CH2-

propyl

2010-11-24

Rulesfornamingorganic compounds(IUPACrules) 1. Identifythe functional functional functional functionalgroup group

Rulesfornamingorganic

compounds(IUPACrules)

1.

Identifythefunctional

functional

functional

functionalgroup

groupofthemolecule–this

group

group

determinestheending

ending ending

endingofthename.

2010-11-24

H

ene ene ene ene Alk 3 H C C C C 2 H C C
ene ene ene
ene
Alk
3
H
C
C
C
C
2
H
C
C
C
C
H
H
C
C
CC
C
C
CC
C
C
CC
C
C
C
C
3
H
C
C
C
C
H
Cl
Cl
Cl
BrCl
Br
Br
Br

C

C

C

C

H

3

chainthat chain carbonchain chain carbon continuouscarbon carbon continuous longestcontinuous continuous longest
chainthat
chain
carbonchain
chain
carbon
continuouscarbon
carbon
continuous
longestcontinuous
continuous
longest
.Findthelongest
longest
2

chain(seetableforprefixes).

accordingtothenumberofcarbonatomsinthe

containsthefunctionalgroup

,andallocateitsprefix

2010-11-24

hex hex 6carbonatoms=hex hex 3 H C C C C 2 H C C C
hex
hex
6carbonatoms=hex
hex
3
H
C
C
C
C
2
H
C
C
C
C
H
H
C
C
C
C
C
C
C
CC
C
C
CC
C
C
CC
C
C
C
H
3
H
C
C
C
C
H
Cl
Cl
BrCl
Cl
Br
Br
Br

H

3

ene

.

.Doubleandtriplebonds number number possiblenumber number possible lowestpossible possible lowest lowest lowest
.Doubleandtriplebonds
number
number
possiblenumber
number
possible
lowestpossible
possible
lowest
lowest
lowest
of
of
carbonof
of
carbon
groupisonthecarbon
carbon
group
group
functionalgroup
functional
themsothatthefunctional
functional
chain.Number
chain.
chain.
thechain.
the
the
inthe
in
atomsin
in
atoms
atoms
carbonatoms
carbon
carbon
thecarbon
the
Numberthe
the
Number
Number
Number
3.

takepreference

preferenceoversidechains

preference

preference

.

2010-11-24

H

. -ene 2 2 2 2 hex- 3 H C C C C 6 2
.
-ene
2
2
2
2
hex-
3
H
C
C
C
C
6
2
H
C
C
C
C
H
H
5
C
C
CC
C
C
CC
C
C
C
CC
C
C
C
234
1
3
H
C
C
C
C
H
Cl
Cl
BrCl
Cl
Br
Br
Br

C

C

C

C

H

3

numberaccordingto number atomsithasandgiveitanumber number atoms atoms carbonatoms carbon carbon carbon of of
numberaccordingto
number
atomsithasandgiveitanumber
number
atoms
atoms
carbonatoms
carbon
carbon
carbon
of
of
of
numberof
number
groupaccordingtothenumber
number
group
group
alkylgroup
alkyl
alkyl
4.Namethealkyl

thecarbonatomitisattachedto.Alkylgroupsmustbe

namedinalphabetical

alphabetical

alphabetical

alphabeticalorder

order

order

order

.

2010-11-24

H

3 H C C C C 6 2 H C C C C H H
3
H
C
C
C
C
6
2
H
C
C
C
C
H
H
5
3
H
C
C
C
C
C
C
CC
C
C
C
CC
C
CC
C
C
C
C
4
3
2
1
3
H
C
C
C
C
H
Cl
Cl
BrCl
Cl
Br
Br
Br

4,4-di-methyl

4,4-di-methyl

4,4-di-methyl

4,4-di-methyl

-hex-2-ene

5.Ifa halogen halogen atomisattachedtothecarbonchain,itis halogen halogen alphabeticalorder alphabetical bromo -,and iodo

5.Ifahalogen

halogenatomisattachedtothecarbonchain,itis

halogen

halogen

alphabeticalorder

alphabetical

bromo-,andiodo

bromo

iodo

iodo

bromo

order

order

order

alphabetical

alphabetical

bromo

treatedasanalkylgroup.Theprefixes:fluoro

fluoro

fluoro

fluoro

chloro

chloro

chloro

-,chloro

iodo–areused.Theymustbenamedin

.

H

3 H C C C C 6 2 H C C C C H H
3
H
C
C
C
C
6
2
H
C
C
C
C
H
H
5
C
C
C
CC
C
C
CC
C
C
CC
C
C
C
4
3
2
1
3
H
C
C
C
C
H
Cl
Cl
Cl
Cl
Br
Br
Br
Br

C

C

C

C

H

3

1-bromo-2-chloro

2010-11-24

-4,4-di-methyl-hex-2-ene

-,

tetrato tetra triandtetra tetra tri ,tri tri di di di ,usetheGreekprefixesdi kind kind kind kind
tetrato
tetra
triandtetra
tetra
tri
,tri
tri
di
di
di
,usetheGreekprefixesdi
kind
kind
kind
kind
same
same
same
groupofthesame
group
group
alkylgroup
alkyl
onealkyl
alkyl
one
thanone
one
than
than
morethan
more
6.Ifthereismore
more

indicatethis.

1,2-di

1,2-di

1,2-di

1,2-di

yne

yne

yne

yne

2010-11-24

-

-

-

-

Cl

H Br Cl C C CC C C CC C C CC C C C
H
Br Cl
C
C
CC
C
C
CC
C
C
CC
C
C
C
C
24
3
1
H
Cl
Cl
BrCl
Cl
Br
Br
Br

5

C

C

C

C

H

3

bromo-

bromo-

bromo-

bromo-

1,1,2-tri

1,1,2-tri

1,1,2-tri

1,1,2-tri

-chloro-pent-2-

-chloro-pent-2-

-chloro-pent-2-

-chloro-pent-2-

Branchedorganicmolecules CH3 CH3 CH3 CH3 CH3 CH3 –CH3 CH3 – – CH2– CH2 CH2 –CH2

Branchedorganicmolecules

CH3 CH3 CH3 CH3 CH3 CH3 –CH3 CH3 – – CH2– CH2 CH2 –CH2 –
CH3
CH3
CH3
CH3
CH3
CH3
–CH3
CH3
CH2–
CH2
CH2
–CH2
CH–
CH
–CH
CH
CH3–
CH3
CH3
CH3
4
4
4
34
3
23
3
2
12
2
1
1 1

2010-11-24

2

2

2

2

methyl-butane

methyl-butane

methyl-butane

methyl-butane

Branchedorganicmolecules CH3 CH3 CH3CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 –CH3 – CH– –

Branchedorganicmolecules

CH3 CH3 CH3CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 –CH3 – CH– – CH
CH3
CH3
CH3CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
–CH3
CH–
CH
–CH
CH
CH–
CH
CH
–CH
CH3–
CH3
CH3
CH3
4
4
4
34
3 3
23
2 2
12
1 1
1

2010-11-24

2,3

2,3

2,3

2,3

di-methyl-butane

di-methyl-butane

di-methyl-butane

di-methyl-butane

Branchedorganicmolecules 2010-11-24 CH3 CH3 CH3 CH3 CH2 CH2 CH2 CH2 1 1 1 1 CH3

Branchedorganicmolecules

2010-11-24

CH3 CH3 CH3 CH3 CH2 CH2 CH2 CH2 1 1 1 1 CH3 CH3 CH3
CH3
CH3
CH3
CH3
CH2
CH2
CH2
CH2
1
1 1
1
CH3
CH3
CH3
CH3
5 5 5 5 4 4 34 4 3 23 3 2 2 2
5 5
5
5
4
4
34
4
3
23
3
2
2 2
CH3 CH3 CH2CH3 CH3 CH2 CH2 CH2 CH2 C C C C CH2 CH2 CH2
CH3
CH3
CH2CH3
CH3
CH2
CH2
CH2
CH2
C
C
C
C
CH2
CH2
CH2
CH3
CH3
CH3
CH3

3-ethyl-3-methyl-pentane

3-ethyl-3-methyl-pentane

3-ethyl-3-methyl-pentane

3-ethyl-3-methyl-pentane

Branchedorganicmolecules 2010-11-24 12 2 2 1 1 1 23 3 3 34 4 4 4

Branchedorganicmolecules

2010-11-24

12

2

2

1

1

1

23

3

3

34

4

4

4

H2C

H2C

H2C

H2C=

=CH

CH

=

=

CH

CH–

–CH

CH

CH

CH–

–CH3

CH3

CH3

CH3

CH3 CH3 CH3 CH3
CH3
CH3
CH3
CH3

3

3

3

3

methyl-but-1

methyl-but-1

methyl-but-1

methyl-but-1-ene

-ene -ene -ene

Branchedorganicmolecules 2010-11-24 CH3 CH3 CH3 CH3 12 2 2 2 1 1 1 34 4

Branchedorganicmolecules

2010-11-24

CH3

CH3

CH3

CH3

12

2

2

2

1

1

1

34

4

4

4

3

3

3

H2C

H2C

H2C

H2C=

=CH

CH

CH

=

=

CH–

–C

C–

C

C

–CH3

CH3

CH3

CH3

CH3 CH3 CH3 CH3
CH3
CH3
CH3
CH3

3,3

3,3

3,3

3,3

di-methyl-but-1-ene

di-methyl-but-1-ene

di-methyl-but-1-ene

di-methyl-but-1-ene

Branchedorganicmolecules 12 1 1 1 23 2 2 3 3 34 4 4 4 HC

Branchedorganicmolecules

12

1

1

1

23

2

2

3

3

34

4

4

4

HC

HC

HC

HC

C–

C

C

C

–CH

CH

CH

CH–

–CH3

CH3

CH3

CH3

CH3 CH3 CH3 CH3
CH3
CH3
CH3
CH3

3-methyl-but-1-yne

3-methyl-but-1-yne

3-methyl-but-1-yne

3-methyl-but-1-yne

2010-11-24

Dienes chain. situatedthroughoutthelongestcontinuouscarbon Thesealkenemoleculescontain twodoublebonds Examples (a)

Dienes

chain.

situatedthroughoutthelongestcontinuouscarbon

Thesealkenemoleculescontaintwodoublebonds

Examples

(a)

2010-11-24

12

1

1

1

23

2

2

3

3

4

4

34

45

5

5

5

H2C

H2C=

=

=

H2C

H2C

=C

C–

C

C

–CH

CH=

CH

CH

=CH

=

CH

=

CH

CH–

–CH3

CH3

CH3

CH3

CH3

CH3

CH3

CH3

2

methyl

penta

1,3-diene –

1,4-diene – hexa – methyl – 2 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3
1,4-diene –
hexa –
methyl –
2
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
6 6
6
6
CH
CH
=CH
CH
=
=
CH=
CH
CH
CH
CH2
CH2
–CH2
CH2
– –
C–
C
=C
C
=
H2C=
=
H2C
H2C
H2C
(b)
2
2
2 2
1
1 1
1
5 5
5
45
4 4
34
3 3
3

(c)

2010-11-24

3

12

1

2

2

1

1

23

34

4

4

4

3

3

H2C

H2C=

H2C

H2C

=C

C

C

=

=

C=

=C

=

C

C

=

C–

–CH3

CH3

CH3

CH3

CH3

CH3

CH3

CH3

methyl

buta

1,2-diene –

Diynes chain. situatedthroughoutthelongestcontinuouscarbon Thesealkynemoleculescontain twotriplebonds Example 12 1 1 1 23

Diynes

chain.

situatedthroughoutthelongestcontinuouscarbon

Thesealkynemoleculescontaintwotriplebonds

Example

12

1

1

1

23

2

2

34

3

3

45

4

4

5

5

5

CH CH CH CH C C C –C – CH– – CH CH –CH –
CH
CH
CH
CH
C
C
C
–C
CH–
CH
CH
–CH
HCC–
HCC
HCC
HCC

2010-11-24

3

methyl

penta

CH3

CH3

CH3

CH3

1,4-diyne –

Isomerism structuralformulaewithmolecularformulae C6H14 Examinethetwostructuralformulaeshownbelow.Bothare C C C C H 3

Isomerism

structuralformulaewithmolecularformulaeC6H14

Examinethetwostructuralformulaeshownbelow.Bothare

C C C C
C
C
C
C

H

3

CHC

CH

C

C

CH

CH

C

C

C

CC

C

C

C

C

H

3

C C C C
C
C
C
C

2

H

3

H

3

2,2-di-methyl-butane

CHCH

CH

CH

CH

C

C

CHC

CH

C

C

C

C

C

CH

H

3

C C C C
C
C
C
C

2

H

3

2-methyl-pentane

ThesetwomoleculesaresaidtobeISOMERS

.

2 H

2-methyl-pentane Thesetwomoleculesaresaidtobe ISOMERS . 2 H formula but differentstructuralformulae Isomers

formulabutdifferentstructuralformulae

Isomers

–organicmoleculeswhichhasthesamemolecular

.

2010-11-24

C

C

C

C

3 H

Alkylhalides(Haloalkanes) Functionalgroup: C CX C C X X X whereX= F , Cl , Br

Alkylhalides(Haloalkanes)

Alkylhalides(Haloalkanes) Functionalgroup: C CX C C X X X whereX= F , Cl , Br ,

Functionalgroup:C

Alkylhalides(Haloalkanes) Functionalgroup: C CX C C X X X whereX= F , Cl , Br ,

CX

C

C

X

X

X

whereX=F

,Cl

,Br

,I

Drawthestructuralformulafor:

(d)3-bromo-2-chloro-2-methyl-butane

(c)2-bromo-2-chloro-1,1,1-trifluoro-ethane

(b)1,1,1-tri-chloro-ethane

(a)chloromethane

2010-11-24

Alcohols products. perfumes,aftershavesandanyotherhousehold Ethanolisusedwidelyasasolventinpaints,glues,

Alcohols

products.

perfumes,aftershavesandanyotherhousehold

Ethanolisusedwidelyasasolventinpaints,glues,

hydrocarbonsofsimilarsize.

havinghighermeltingandboilingpointsthan

Thestronghydrogenbondsinalcoholsresultinalcohols

Functionalgroup:C

than The stronghydrogenbonds inalcoholsresultinalcohols Functionalgroup: C COH C C OH OH OH Hydroxylgroup 2010-11-24

COH

C

C

OH

OH

OHHydroxylgroup

2010-11-24

Alcohols anda polar polar polar Alcoholmoleculeshavea non-polar non-polar non-polar non-polar hydrocarbonend polar –

Alcohols

andapolar

polar

polar

Alcoholmoleculeshaveanon-polar

non-polar

non-polar

non-polarhydrocarbonend

polar

OHsection.

Polarend
Polarend
end polar Non-
end
polar
Non-

Alcoholsaresolventsforpolarandnon-polarsolutes.

2010-11-24

Alcohols thelongestchainbeginningattheendnearestthe Alcoholsarenamedusingtheending– ol .Number hydroxylgroup.(OH)

Alcohols

thelongestchainbeginningattheendnearestthe

Alcoholsarenamedusingtheending–

ol

.Number

hydroxylgroup.(OH)

Alcoholsarenamedusingtheending– ol .Number hydroxylgroup.(OH) ethanolpropan-1-ol2-methyl-propan-1-ol 2010-11-24
Alcoholsarenamedusingtheending– ol .Number hydroxylgroup.(OH) ethanolpropan-1-ol2-methyl-propan-1-ol 2010-11-24

ethanolpropan-1-ol2-methyl-propan-1-ol

Alcoholsarenamedusingtheending– ol .Number hydroxylgroup.(OH) ethanolpropan-1-ol2-methyl-propan-1-ol 2010-11-24
Alcoholsarenamedusingtheending– ol .Number hydroxylgroup.(OH) ethanolpropan-1-ol2-methyl-propan-1-ol 2010-11-24

2010-11-24

Alcohols Pentan-3-ol Butan-2-ol Propan-2-ol 2010-11-24

Alcohols

Pentan-3-ol Butan-2-ol Propan-2-ol
Pentan-3-ol
Butan-2-ol
Propan-2-ol

2010-11-24

Alcohols 2-methyl-butan-2-ol 2-methyl-propan-2-ol 2010-11-24 OH OH OHOH OH OH OHOH OH OH OH OH CH2

Alcohols

2-methyl-butan-2-ol 2-methyl-propan-2-ol
2-methyl-butan-2-ol
2-methyl-propan-2-ol

2010-11-24

OH OH OHOH OH OH OHOH OH OH OH OH CH2 CH2 –CH2 CH2 –
OH
OH
OHOH
OH
OH
OHOH
OH
OH
OH
OH
CH2
CH2
–CH2
CH2
CH–
CH
CH
–CH
CH2–
CH2
CH2
CH2

Propan–1,2,3,-triol

Glycerine/Glycerol

Alcohols with strongoxidizingagents Alcoholsare oxidized to carboxylicacids whentreated . 2010-11-24

Alcohols

withstrongoxidizingagents

Alcoholsareoxidizedtocarboxylicacidswhentreated

.

Alcohols with strongoxidizingagents Alcoholsare oxidized to carboxylicacids whentreated . 2010-11-24

2010-11-24

Carboxylicacids ants. (CHOOH).Thisacidcanbefoundinstingingnettlesand Thefirstmemberoftheacidseriesis methanoicacid O C C

Carboxylicacids

ants.

(CHOOH).Thisacidcanbefoundinstingingnettlesand

Thefirstmemberoftheacidseriesismethanoicacid

O

C C C HC
C
C
C
HC

OH

O

methanoicacid O C C C HC OH O Functionalgroup: Carboxylgroup C C C C OH acids.

Functionalgroup:CarboxylgroupC

C

C

C

OH

acids.

Thenamesendin–

2010-11-24

oicacid

.Theyarerelativelyweak

Carboxylicacids Ethanoicacid isthesourcomponentofvinegar. 2010-11-24 CH 3 O C C C C OH

Carboxylicacids

Ethanoicacidisthesourcomponentofvinegar.

2010-11-24

CH

3

O

C C C C
C
C
C
C

OH

Carboxylicacids butter. Butanoicacid givestheunpleasantsmelltorancid 2010-11-24 CH 3 CH O C C C C 2 OH

Carboxylicacids

butter.

Butanoicacidgivestheunpleasantsmelltorancid

2010-11-24

CH

3CH

O

Carboxylicacids butter. Butanoicacid givestheunpleasantsmelltorancid 2010-11-24 CH 3 CH O C C C C 2 OH CH

C

C

C

C

2OH

CH

2

Carboxylicacids O O CH3O O CH3 CH3 CH3 OH OH -OH OH - - C-

Carboxylicacids

O O CH3O O CH3 CH3 CH3 OH OH -OH OH - - C- C
O
O
CH3O
O
CH3
CH3
CH3
OH
OH
-OH
OH
-
-
C-
C
C
–C
CH2–
CH2
–CH2
CH2
C–
C
–C
C
CH3–
CH3
CH3
CH3
1 1
1
1
2 2
2
2
3
3
3 3
4
4
4
4
CH3
CH3
CH3
CH3

3,3-di-methyl-butanoicacid

acid

acid

3,3-di-methyl-butanoic

3,3-di-methyl-butanoic

3,3-di-methyl-butanoic

acid

2010-11-24

Nomenclature

(COOH)

atthecarboxylgroup.

carbonchainbeginning

Numberthelongest

Esters Estersarethecompoundswhicharelargelyresponsible assolventsandadhesives.

Esters

Estersarethecompoundswhicharelargelyresponsible

assolventsandadhesives.

areusedasfoodflavouringsandinperfumesandused

fortheflavoursandscentsoffruitsandflowers.Esters

O

fortheflavoursandscentsoffruitsandflowers.Esters O Functionalgroup: C C C C 2010-11-24 O C C C C

Functionalgroup:C

C

C

C

2010-11-24

fortheflavoursandscentsoffruitsandflowers.Esters O Functionalgroup: C C C C 2010-11-24 O C C C C

OC

C

C

C

Esters carboxylicacid condensationreactionbetweenan alcohol anda Anesteristheproductofanacidcatalysed O O O O .

Esters

carboxylicacid

condensationreactionbetweenanalcoholanda

Anesteristheproductofanacidcatalysed

O

O

O

O

.

Nomenclature

ACID.Thenameendsin-

suffixfromthenameofthe

theALCOHOLandthe

theesterisderivedfrom

Theprefixinthenameof

ALCOHOL andthe theesterisderivedfrom Theprefixinthenameof C C C CH3 CH3 CH3 CH3- - - - CH3 CH3

C

C

C

CH3

CH3

CH3

CH3-

-

-

-CH3

CH3

CH3

C-

-

-

-O

O

O

O-

-

-

-

CH3

CH3 CH3 CH3- - - - CH3 CH3 CH3 C- - - - O O O

AcidAlcohol

Alcohol

Acid

Acid

Acid

Alcohol

Alcohol

methyl

methyl

methylethanoate

methyl

ethanoate

ethanoate

ethanoate

OATE

2010-11-24

Methanol

Methanol

Methanol

Methanol

Ethanoic

Ethanoicacid

acid

acid

acid

Ethanoic

Ethanoic

Esterformation(esterification) dehydratingagent Actsasa catalyst and O O O O CH3 – CH3 CH3 CH3 –

Esterformation(esterification)

dehydratingagent

Actsasacatalystand

O

O

O

O

CH3

CH3

CH3

CH3

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

C

C

C

C-

-

-

-

butanoicacid

H

2SO

4

(Concentrated)

) ’ bridge ‘ ( O O O O Oxygenlink propan-1-ol CH3 CH3 CH3 CH2CH3
)
bridge
(
O
O
O
O
Oxygenlink
propan-1-ol
CH3
CH3
CH3
CH2CH3
CH2
CH2CH2
CH2
CH2
OCH2
CH2
O
O
O
H
H
H
H
+
OH
OH
OH
OH

CH3

CH3

CH3

CH3

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

C

C

C

-

C-

-

-

OCH2

O

O

O

CH2CH2

CH2

CH2

CH2

CH2

CH3

CH3

CH2CH3

CH3

+

H2O

H2O

H2O

H2O

butanoicacid+propan-1-ol

H

2

SO

4

(Concentrated)

H2O H2O butanoicacid + propan-1-ol H 2 SO 4 (Concentrated) propyl butanoate + carboxylicacid + alcohol

propylbutanoate+

+ propan-1-ol H 2 SO 4 (Concentrated) propyl butanoate + carboxylicacid + alcohol ester + 2010-11-24

carboxylicacid+alcoholester+

2010-11-24

water

water

ethanoicacid + ethanolethyl ethanoate +water molecule. NB.Usetheoxygenatomasadividerwhennamingthe 2010-11-24

ethanoicacid

ethanoicacid + ethanolethyl ethanoate +water molecule. NB.Usetheoxygenatomasadividerwhennamingthe 2010-11-24

+ethanolethylethanoate+water

molecule.

NB.Usetheoxygenatomasadividerwhennamingthe

2010-11-24

Namethefollowing - - - C- C C –C – – CH2– CH2 CH2 –CH2 –

Namethefollowing

- - - C- C C –C – – CH2– CH2 CH2 –CH2 – –
- -
-
C-
C
C
–C
– –
CH2–
CH2
CH2
–CH2
– –
CH3–
CH3
CH3
CH3
O
O
O
O
CH3 CH3 CH3 CH3CH3 CH3 CH3 CH2CH3 CH2 CH2CH2 CH2 CH2 CH2
CH3
CH3
CH3
CH3CH3
CH3
CH3
CH2CH3
CH2
CH2CH2
CH2
CH2
CH2

OCH2

O

O

O

CH3 CH3 CH2CH3 CH2 CH2CH2 CH2 CH2 CH2 OCH2 O O O butyl propanoate CH3 CH3

butyl

propanoate

CH3 CH3 CH3CH3 CH3 CH3 CH2CH3 CH3 CH2 CH2 CH2CH2 CH2 CH2 CCH2 C C
CH3
CH3
CH3CH3
CH3
CH3
CH2CH3
CH3
CH2
CH2
CH2CH2
CH2
CH2
CCH2
C
C
C
O
O
O
O
CH3 CH2 CH2 CH2CH2 CH2 CH2 CCH2 C C C O O O O – –
– – CH3– CH3 CH3 CH3
– –
CH3–
CH3
CH3
CH3

O

O

O

O-

-

-

-

methylpentanoate

2010-11-24

+

butan-1-ol

REACTANTS

propanoicacid

+

methanol

pentanoicacid

Drawtheproducts H C C C HC H OH H O +C C C C C

Drawtheproducts

H

C C C HC
C
C
C
HC

H

OH

H

O

Drawtheproducts H C C C HC H OH H O +C C C C C HOH

+CC

C

C

C

HOH

Drawtheproducts H C C C HC H OH H O +C C C C C HOH

H

methanolethanoicacid

H

2SO

4

(Concentrated)

C C C C HOH H methanolethanoicacid H 2 SO 4 (Concentrated) 2010-11-24 H H H

2010-11-24

H

H H C C C C C O C C C C H O H
H
H
C
C
C
C
C
O
C
C
C
C
H
O
H

H

methylethanoate

+H2O

H2O

H2O

H2O

Aldehydes Functionalgroup: O CH C C C carbonyl group group group group theC=Oonanoutercarbonis polar polar

Aldehydes

Functionalgroup:

O

CH C C C
CH
C
C
C

carbonylgroup

group

group

group

theC=Oonanoutercarbonispolar

polar

Thesimplestaldehydeismethanal(Formaldehyde).Inaldehydes,

polar

polar

.

H

O

CH C C C
CH
C
C
C

Nomenclature

group.

Thelongestchainisnumberedbeginningattheendnearesttothecarbonyl

Aldehydesarenamedbyattachingthesuffix‘

al

al

al

al

.

-

2010-11-24

Aldehydes 1. H H H H H H H H - C = O Methanal

Aldehydes

1.

H

H

H

H

H H H H
H
H
H
H

-C=O

Methanal

2.

H-C=O H H H CH3 CH3 CH3 CH3
H-C=O
H
H
H
CH3
CH3
CH3
CH3

Ethanal

3.

H-C=O H H H CH3 CH3 -CH3 CH3 - - - CH2 CH2 CH2 CH2
H-C=O
H
H
H
CH3
CH3
-CH3
CH3
- -
-
CH2
CH2
CH2
CH2

Propanal

2010-11-24

5.

4.

H

H

H

H

methylbutanal – 3 -C=O CH3 CH3 CH3 -CH3 - - - CH CH CH -CH
methylbutanal –
3
-C=O
CH3
CH3
CH3
-CH3
-
- -
CH
CH
CH
-CH
-
- -
CH2
CH2
CH2
CH2
CH3
CH3
CH3
CH3
CH CH CH CH CH3 CH3 CH3 CH3
CH
CH
CH
CH
CH3
CH3
CH3
CH3

-CH2

-

-

-

CH2-

CH2

CH2

-CH

-

-

CH-

CH

CH

-

-

-CH2

CH2-

CH2

CH2

-CH3

CH3

-

-

CH3

CH3

CH3 CH3 CH3 CH3
CH3
CH3
CH3
CH3

H

H

H

H-C=O

2,4-di-methylhexanal

Functionalgroup: Ketones O C C C C carbonyl group group group group Ina ketone

Functionalgroup:

Ketones

O

C C C C
C
C
C
C

carbonylgroup

group

group

group

Inaketone

,thecarbonatominthecarbonylgroupisbondedtoa

carbononbothsides.Thesimplestketoneispropanone(acetone).

CH

3

O

C C C C
C
C
C
C

CH

3

Inketones,theC=O(carbonylgroup)onaninnercarbonispolar

polar

polar

polar

2010-11-24

.

Ketones Nomenclature one Ketones(R–CO–R ’ . � )arenamedbyattachingthesuffix‘– number. carbonylgroup

Ketones

Nomenclature

one

Ketones(R–CO–R

.

)arenamedbyattachingthesuffix‘–

number.

carbonylgroup

Thelongestchainisnumberedbeginningattheendnearesttothe

.TheCinthecarbonylgrouphasthelowest

2010-11-24

Ketones 1.3. O O CH3CH3 CH3 CH3 CH3 CH3 CH3 CH3 -C- CH3CH CH3 CH3

Ketones

1.3.

O

O

CH3CH3

CH3

CH3

CH3

CH3

CH3

CH3

-C-

CH3CH

CH3

CH3

CH3

CHCH2

CH

CH

C-

CH2CH2

CH2

CH2

CH2CH3

CH2

CH3

CH2

CH3

CH3

CH3 CH3 CH3 CH3
CH3
CH3
CH3
CH3

propanone

2

methylhexan-3-one –

O 2.

CH3CH2

CH2

CH3

CH3

CH3

CH2

CH2CH2

-C-

CH2CH2

CH2

CH2

CH2CH3

CH2

CH3

CH3

CH3

CH2

hexan-3-one

4.

O

CH3 CH3 CH3 CH3
CH3
CH3
CH3
CH3

CH3CH

CH3

CH3

CH3

-C-

CHCH2

CH

CH

CH2CH

CH2

CH

CH

CH2

CHCH3

CH3

CH3

CH3

CH3 CH3 CH3 CH3
CH3
CH3
CH3
CH3

2010-11-24

2,5-di-methyl-hexan-3-one

Intermolecularforces liquidorgasphase. Intermolecularforcesexist betweenmolecules inthesolid, liquidstogases

Intermolecularforces

liquidorgasphase.

Intermolecularforcesexistbetweenmoleculesinthesolid,

liquidstogases

Thestrengthoftheseforcesdecreasesfromsolidsto

.

intermolecularforceswithinthesubstance.

Highermeltingandboilingpointsindicatestronger

increasingsizeofthemolecule

Thestrengthoftheintermolecularforcesincreaseswith

.

2010-11-24

VanderWaalsforces positiveandnegativecharges. Theseare weakforces betweenparticlescarrying small

VanderWaalsforces

positiveandnegativecharges.

Theseareweakforcesbetweenparticlescarryingsmall

arelargeincomparisontothesizeofthemolecule.

Theyarenon-directionalandactoverdistanceswhich

2010-11-24

VanderWaalsforces 1.Dipole-dipole: andtheendofanother. Attractionbetweentheendofone polarmolecule δ δ δ δ+