Ch21 (EE).ppt

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New Way Chemistry for Hong Kong A-Level Book 3A1

1

Introduction toIntroduction toOrganic ChemistryOrganic Chemistry

21.121.1 What is Organic Chemistry?What is Organic Chemistry?

21.221.2 The Unique Nature of CarbonThe Unique Nature of Carbon

21.321.3 Classification of Organic CompounsClassification of Organic Compouns

21.!21.! "actors #ffecting the $hysical $roperties of"actors #ffecting the $hysical $roperties ofOrganic CompounsOrganic Compouns

2121

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New Way Chemistry for Hong Kong A-Level 3A2

21.21.

11 What isWhat isOrganicOrganic

Chemistry?Chemistry?

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21.1 What is Organic Chemistry %&' p.2(

Organic ChemistryO

rganic Chemistry

) Chemistry of the compounds presentin living organisms.

) They all contain carbon.

• Organic Chemistry is the Chemistryof Carbon.

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Livingthings

Carbohydrates /Proteins / Fats /Vitamins /ntibiotics

21.1 What is Organic Chemistry %&' p.!(

!atural "ources of Organic Compounds!atural "ources of Or

ganic Compounds

variety oforganic productsobtained fromliving things

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New Way Chemistry for Hong Kong A-Level Book 3A

New Way Chemistry for Hong Kong A-Level 3A

Crude oilor coal

Fractional distillation /destructive distillation

l#anes /l#enes /l#ynes /

romatichydrocarbons


!atural "ources of Organic Compounds!atural "ources of Or

ganic Compounds

variety ofuseful productsderived from

crude oil and coal

Check Point 21-1Check Point 21-1

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New Way Chemistry for Hong Kong A-Level Book 3A!

New Way Chemistry for Hong Kong A-Level 3A!

$n the past%&

Chemistry

Chemistry

Organiccompounds

Organiccompounds

obtained fromliving organisms

$norganiccompounds

$norganiccompounds

obtained fromnon'living sources


(evelopment of Organic Chemistry(evelo

pment of Organic Chemistry

as a "cienceas a "cience

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New Way Chemistry for Hong Kong A-Level Book 3A" New Way Chemistry for Hong Kong A-Level 3A"

%*norganic

compoun(%Organic

compoun(

$n )*+*& ,ohler -a erman chemist


(evelopment of Organic Chemistry(evelopment of Organic Chemistry


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New Way Chemistry for Hong Kong A-Level Book 3A# New Way Chemistry for Hong Kong A-Level 3A#

0edefining % ...

Organic chemistry is the study of carboncompounds -e1cept CO& CO+& carbonates&

hydrogencarbonates& carbides andcyanides obtained from natural sources or

synthesi2ed in the laboratories.

Organic chemistry is the study of carboncompounds -e1cept CO& CO+& carbonates&

hydrogencarbonates& carbides andcyanides obtained from natural sources orsynthesi2ed in the laboratories.

(evelopment of Organic Chemistry(evelopment of Organic Chemistry



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21.21.

22 The UniqueThe UniqueNature ofNature of

CarbonCarbon

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New Way Chemistry for Hong Kong A-Level Book 3A1% New Way Chemistry for Hong Kong A-Level 3A1%

21.2 The Unique Nature of Carbon %&' p.+(

bility to form fourbility to form four strongstrong covalent bondscovalent bonds

Carbon -ground state

• 3lectronic configuration of carbon-ground state 4 )s++s++p+

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• 3ach carbon atom has four unpairedelectrons 5hen e1cited

• Tend to form four strong covalent bonds

Carbon -e1cited state

bility to form fourbility to form four strongstrong covalent bondscovalent bonds

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• Carbon atoms lin# together to formchains of varying length& branchedchains and rings of different si2es

) Catenation4

bility of atoms in forming stable

bonds 5ith itself& hence 6oining upinto chains or rings

bility to Catenatebilit y to Catenate

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C 7 C 8 "i 7 "i 8 e 7 e 8 "n 7 "n

9ond strength ↓ as bond length ↑

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C 7 C 8 ! 7 ! 8 O 7 O

9ond strength ↓

as the number of lone pairs ↑

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Cn:+n;+ n < )&+&=&%-no limit for n

"in:+n;+ n < ) to > only → silanes

en:+n;+ n < ) to = only → germanes

"nn:+n;+ Only "n:? -stannane e1ists

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Single bond Double bond Triple bond

21.2 The Unique Nature of Carbon %&' p.-(

/ 0 halogens

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New Way Chemistry for Hong Kong A-Level Book 3A1# New Way Chemistry for Hong Kong A-Level 3A1#


Example 21-2Example 21-2 Check Point 21-2Check Point 21-2

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New Way Chemistry for Hong Kong A-Level Book 3A1$ New Way Chemistry for Hong Kong A-Level 3A1$

21.21.33ClassicationClassicationof Organicof Organic

Comoun!sComoun!s

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• Organic compounds are classified bythe the presence of characteristic

functional groups.

21.3 Classification of Organic Compouns %&' p.(

Functional roupsFunctional roups

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functional group is defined as anatom or a group of atoms that

effectively determines the chemicalproperties of an organic compound.

functional group is defined as anatom or a group of atoms thateffectively determines the chemicalproperties of an organic compound.



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21 3 C f f O C %& (

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• Propane does not react 5ith sodium

• 3thanol and propan')'ol react 5ithsodium to give hydrogen gas

21 3 Cl ifi ti f O i C %&' (

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• have similar chemical properties

they contain the same functional group 7O: they are classified into the samehomologous series A alcohols

an



21 3 Cl ifi ti f O i C %&' 12(

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:omologous "eries:omologous "eries

21.3 Classification of Organic Compouns %&' p.12(

homologous series is a series ofcompounds that have the same functional

group& and each member differs fromthe ne1t member by a 7 C:+ 7 unit in

their formulae.

homologous series is a series ofcompounds that have the same functional

group& and each member differs fromthe ne1t member by a 7 C:+ 7 unit in

their formulae.

C:? C+:> C=:* C?:)B

C:+ C:+ C:+

21 3 Cl ifi ti f O i C %&' 12(

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New Way Chemistry for Hong Kong A-Level Book 3A2! New Way Chemistry for Hong Kong A-Level 3A2!


Number ofcarbonatoms!

I"#$Cname

%olecularformula

Condensedstructuralformula

Structuralformula

1 ethane C! C!

2 4thane C2- C3C3

3 $ropane C35 C3C2C3

! 'utane C!16 C3C2C2C3

The first four members of strai ht'chain al#anes

21 3 Cl ifi ti f O i C %&' 12(

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Number ofcarbonatoms!

I"#$Cname

%olecularformula

Condensedstructuralformula

Structuralformula

1 ethanol C3O C3O

2 4thanol C2+O C3C2O

3 $ropan717ol

C3O C3C2C2O

! 'utan717ol

C!8O C3C2C2C2O

The first four members of strai ht'chain alcohols

21 3 Cl ifi ti f O i C %&' 13(

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New Way Chemistry for Hong Kong A-Level Book 3A2# New Way Chemistry for Hong Kong A-Level 3A2#

• @embers in the same series can berepresented by a general formula.

e.g. al#anes4 Cn:+n;+

al#enes4 Cn:+n

al#ynes4 Cn:+n'+



21 3 Classification of Organic Compouns %&' p 13(

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• @embers in the same series can berepresented by a general formula.



e.g. al#anols4 Cn:+n;)O:

al#anals4 Cn:+n;)C:O

al#anoic acids4 Cn:+n;)COO:


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Functional groupof an organic

compound

Chemicalproperties

@embers of a homologous serieshave similar chemical properties




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• The physical properties change gradually along the homologous series

• e.g. the longer the carbon chain in the

molecule - or the greater themolecular mass

the greater the attractive force

bet5een molecules the higher the melting point&

boiling point and density




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Numberof

carbonatoms!

%olecularformula

State atroom

temperatureand

pressure!

%eltingpoint &C!

'oilingpoint &C!

Density ofsolid ( li)uid at2*&C g cm +3!

1

2

3

!

+-

5

8

16

C!C2-

C35

C!16

C+

12

C-1!

C1-

C515

C826

C1622

9as

9as

9as

9as

:iqui:iqui

:iqui

:iqui

:iqui

:iqui

;153

;12

;155

;13+

;136 ;8+

;81

;+

;+!

;36

;1-1

;58

;!2

6

3--8

85

12-

1+1

1!

;

;

;

;

6.-2-6.-+

6.-5!

6.63

6.15

6.36

"ome physical properties of the first +B members ofstraight'chain al#anes



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Numberof

carbonatoms!

%olecular formula

State at

roomtemperature

andpressure!

%eltingpoint &C!

'oilingpoint &C!

Density ofsolid ( li)uid at2*&C g cm +3!

11

12

13

1!

1+

1-

1

15

18

26

C11

2!

C122-

C1325

C1!36

C1+32

C1-3!

C13-

C1535

C18!6

C26!2

:iqui

:iqui

:iqui

:iqui

:iqui

:iqui

:iqui

&oli

&oli

&oli

;2-

;16

;

;3

16

15

22

25

32

3

18-

21-

233

2-6

21

25

362

31-

336

3!!

6.!6

6.!8

6.+3

6.-1

6.-8

6.3

6.5

6.

6.

6.5+

"ome physical properties of the first +B members ofstraight'chain al#anes



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Example 21-3AExample 21-3A Example 21-3BExample 21-3B

Example 21-3CExample 21-3C Check Point 21-3Check Point 21-3

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21.21.

" "#actors $%ecting#actors $%ecting

the &hysicalthe &hysical&roerties of&roerties of

OrganicOrganic

Comoun!sComoun!s

0efer to notes on 9onding and "tructureDpp.EE'+ 7 intermolecular forces

21 , "actors #ffecting the $hysical $roperties of Organic Compouns

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New Way Chemistry for Hong Kong A-Level Book 3A3! New Way Chemistry for Hong Kong A-Level 3A3!

). "tructure of the functional group).) (ipole moment of the molecule

).+ Formation of hydrogen bonding

+. Length of carbon chains -Londondispersion forces

21., "actors #ffecting the $hysical $roperties of Organic Compouns

%&' p.1(

@ain Factors ffecting the@ain Factors ffecting the

Physical Properties of OrganicPhysical Properties of OrganicCompoundsCompounds


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• @olecules having a polar functionalgroup have a higher b.p. than others

5ith a non'polar functional group ofsimilar molecular masses

"tronger intermolecular attraction

among molecules


%&' p.1(

"tructure of Functional roup"tructure of Functional roup


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New Way Chemistry for Hong Kong A-Level Book 3A3# New Way Chemistry for Hong Kong A-Level 3A

3#


%&' p.1(

"tructure of Functional roup"tructure of Functional roup

%olecule -elatiemolecular

mass

'oiling pointoC!

%olecules

/ith polarfunctionalgroups

C3C2C2O -6 8.2

C3C2C2N2 +8 !5.-

C3C2Cl -!.+ 12.+

C3C2COO -6 1!1

%olecules/ith non0

polarfunctional

groups

C3C2C2C3 +5 76.+

C3C2C0C2 +- 7-.2

C3C2C≡C +! 5.1


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3$


%&' p.15(

(ipole @oment of @olecule(ipole @oment of @olecule

• Tetrachloromethane has ? polar bonds in the molecule

• @.p. and b.p. are very lo5

the molecule is non'polar

the molecule is tetrahedrallysymmetrical

the dipole moments of theC Cl bond cancel each other


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New Way Chemistry for Hong Kong A-Level Book 3A4% New Way Chemistry for Hong Kong A-Level 3A

4%


%&' p.15(

31amples of Polar @olecules31amples of Polar @olecules

5ith !et (ipole @oment5ith !et (ipole @oment


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New Way Chemistry for Hong Kong A-Level Book 3A41 New Way Chemistry for Hong Kong A-Level 3A

41


%&' p.15(

31amples of !on'polar @olecules31amples of !on'polar @olecules

5ith !o !et (ipole @oment5ith !o !et (ipole @oment


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42


%&' p.15(

"olubility of Organic @olecules"olubilit y of Organic @olecules

• (epends on the polarity of organicmolecules and the solvent

• !on'polar or 5ea#ly polar compounds dissolve readily in non'polar or 5ea#lypolar solvents

• :ighly polar compounds dissolve readily

in highly polar solvents• GLi#e dissolves li#eH


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43


%&' p.15(

"olubility of Organic @olecules"olubilit y of Organic @olecules

:e1ane intetrachloromethane

:e1ane in 5ater


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44


%&' p.18(

,hy does :e1ane (issolve 0eadily in,hy does :e1ane (issolve 0eadily in

TetrachloromethaneITetrachloromethaneI

*ntermolecular forces amonghe,ane molecules an those

among tetrachloromethane

molecules

≈

*ntermolecular forcesbet

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4

g y p g p

%&' p.18(

,hy is :e1ane $nsoluble in ,aterI,hy is :e1ane $nsoluble in ,aterI


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4!

g y p g p

%&' p.18(

Formation of :ydrogen 9ondingFormation of : ydrogen 9onding

• @olecules having O: or !:+ groupsare able to form hydrogen bonds

• :ydrogen bonds affect the physical

properties of alcohols and amines 5ithlo5 molecular masses


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New Way Chemistry for Hong Kong A-Level Book 3A4" New Way Chemistry for Hong Kong A-Level 3A

4"

g y p g p

%&' p.26(

,hy does Propan')'ol have a,hy does Propan')'ol have a

:igher 9oiling PointI:igher 9oiling PointI


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4#

g y p g p

%&' p.26(

Formation of :ydrogen 9ondingFormation of : ydrogen 9onding

• lso affect the solubility of a molecule

• @olecules 5ith O: groups are able

to form hydrogen bonds 5ithsurrounding 5ater molecules

"oluble in 5ater


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g y p g p

%&' p.26(

Example 21-4AExample 21-4A

Example 21-4BExample 21-4B


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New Way Chemistry for Hong Kong A-Level Book 3A% New Way Chemistry for Hong Kong A-Level 3A%

g y g

%&' p.21(

Length of Carbon ChainsLength of Carbon Chains

• @olecules 5ith higher molecular masses have higher m.p.& b.p. and density

:igher molecular masses Large molecular si2es

"tronger London dispersion

forces among molecules


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%&' p.21(


• @olecules 5ith branched chains

b.p. and density lo5er than its

straight'chain isomer "traight'chain isomers have greater

surface area in contact 5ith each other

reater attractive force among themolecules


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%&' p.21(


• @olecules 5ith branched chains

m.p. higher than its straight'chain isomer

9ranched'chain isomers are morespherical

Pac#ed more efficiently in solid state

31tra energy is needed to brea#do5n the efficient pac#ing


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%&' p.21(

Example 21-4CExample 21-4C

Check Point 21-4Check Point 21-4


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amilyeneralformula

unctionalgroup

4ample

ormula I"#$C name

#l=ane > %Nil( C3C3 4thane

#l=ene

>C 0 C2

>C 0 C>

>2C 0 C>

>2C 0 C>2

Carbon7

carbonouble bon

C2 0 C2 4thene

#l=yne>C ≡ C

>C ≡ C>

; C ≡ C ;

Carbon7carbon triple

bon

C ≡ C 4thyne

#romatichyrocarbon

#r

$henyl group

'enene

> 0 Cn

2n@1

;


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New Way Chemistry for Hong Kong A-Level Book 3A New Way Chemistry for Hong Kong A-Level 3A

amilyeneralformula

unctionalgroup

4ample

ormula I"#$C name

aloal=ane >/ /

halo groupC3Cl Chloromethane

#lcohol >O O

hyro,yl group

C3O ethanol

4ther > O > O

o,y group

C3 O

C3etho,ymethane

#lehye

carbonyl group

ethanal

> 0 Cn2n@1 ;


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New Way Chemistry for Hong Kong A-Level Book 3A! New Way Chemistry for Hong Kong A-Level 3A!

amilyeneralformula

unctionalgroup

4ample

ormula I"#$C name

Aetone

carbonyl group

$ropanone

Carbo,ylicaci

carbo,yl group

4thanoic aci

#mine>N2>2N

>3N amino group

C3N2 ethylamine

Nitrile >C≡N C ≡ N

nitrile group

C3CN 4thanenitrile

> 0 Cn2n@1 ;


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New Way Chemistry for Hong Kong A-Level Book 3A" New Way Chemistry for Hong Kong A-Level 3A"

amilyeneralformula

unctionalgroup

4ample

ormula I"#$C name

4ster

ester group

ethylethanoate

#cyl halie

acyl haliegroup

4thanoylchlorie

#mie

amie group

4thanamie

> 0 Cn2n@1 ;


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New Way Chemistry for Hong Kong A-Level Book 3A# New Way Chemistry for Hong Kong A-Level 3A#

amily eneralformula unctionalgroup

4ample

ormula I"#$C name

#ci

anhyrie aci anhyriegroup

4thanoic

anhyrie

> 0 Cn2n@1 ;

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The ND


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New Way Chemistry for Hong Kong A-Level Book 3A!% New Way Chemistry for Hong Kong A-Level 3A!%

(a)How was organic chemistry defnedbeore 1800s?

ns5er%a( The =no

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New Way Chemistry for Hong Kong A-Level Book 3A!1 New Way Chemistry for Hong Kong A-Level 3A!1

(b) How is organic chemistry defnednowadays?

Back

ns5er%b( No

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,hy is carbon able to catenateI

Back

ns5erThe ability to catenate of carbon is chiefly ue tothe high strength of the C C single bon %bon

enthalpy of C C single bon is 3+- =D mol71(.


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Would you expect silicon which is !ust belowcarbon in the "eriodic #able to catenate to ormdi$erse molecular structures? %xplain youranswer& ns5er

&ilicon unli=e carbon oes not catenate to form iBerse

molecular structures. Carbon is able to catenate because

carbon atoms haBe a relatiBely small atomic sie. This

enables a carbon atom to form strong coBalent bons

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Would you expect sulphur which has anelectronegati$ity $alue $ery close tocarbon to catenate? Why?

Back

ns5er

The electronic configuration of sulphur is 1s22s22p-3s23p!. *t

has only t

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New Way Chemistry for Hong Kong A-Level Book 3A! New Way Chemistry for Hong Kong A-Level 3A!

'dentiy the unctional group(s) in the ollowing

compounds(a)

ns5er%a( Carbon7carbon ouble bon % ( an

chloro group % Cl(

21.3 Classification of Organic Compouns %&' p.1!(

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compounds(b)

ns5er%b( Carbonyl group % (

21.3 Classification of Organic Compouns %&' p.1!(

k

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compounds(c)

ns5er%c( #mino group % ( an carbo,yl group

% (

Back

21.3 Classification of Organic Compouns %&' p.1+(

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New Way Chemistry for Hong Kong A-Level Book 3A!# New Way Chemistry for Hong Kong A-Level 3A!#

#o which homologous series does each o theollowing compounds belong?

(a)

ns5er

%a( 4ster


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New Way Chemistry for Hong Kong A-Level 3A!$


(b)

ns5er

%b( #mie


B k

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New Way Chemistry for Hong Kong A-Level 3A"%


(c)

ns5er

%c( #ci anhyrie

Back


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New Way Chemistry for Hong Kong A-Level Book 3A"1

New Way Chemistry for Hong Kong A-Level 3A"1

tate whether each o the ollowing pairs ocompounds belongs to the same homologousseries& %xplain your answer&

(a)

ns5er%a( No the first one is a carbo,ylic aci an thesecon one is an ester.


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(b)

ns5er%b( Ees both of them are alcohols.


B k

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(c)

ns5er%c( No the first one is an amie anthe secon one is an amine.

Back

21.3 Classification of Organic Compouns %&' p.1-(

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(a) *ame the homologous series o organiccompounds that contain oxygen atoms intheir unctional groups&

ns5er%a( #lcohol ether alehye =etonecarbo,ylic aci ester acyl halieamie an aci anhyrie


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New Way Chemistry for Hong Kong A-Level 3A"

(b) 'dentiy and name the unctional groups inglucose which has the ollowing structure&

ns5er

%b( O %hyro,yl group(

an O %o,ygroup(


B k

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New Way Chemistry for Hong Kong A-Level 3A"!

(c) 'dentiy and name the unctional groups inthe ollowing compounds

ns5er

Back

%c( 'r %bromo(

%alehye(

%acyl chlorie(

%carbon7carbonouble bon( groups


%&' p.15(

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New Way Chemistry for Hong Kong A-Level Book 3A""

New Way Chemistry for Hong Kong A-Level 3A""

%&' p.15(

,hy is oil immiscible 5ith 5aterI

ns5erOil molecules o not haBe free O groupsso they cannot form hyrogen bons

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New Way Chemistry for Hong Kong A-Level Book 3A"#

New Way Chemistry for Hong Kong A-Level 3A"#

%&' p.26(

The relative molecular mass of glucose is )*B.B& but itis soluble in 5ater. ,hyI

ns5er9lucose molecules haBe O groups so

they are able to form hyrogen bons

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New Way Chemistry for Hong Kong A-Level Book 3A"$

New Way Chemistry for Hong Kong A-Level 3A"$

%&' p.26(

+espite the act that butan,1,ol andethoxyethane ha$e the same relati$e molecularmass they ha$e $ery di-erent boiling points&#he boiling points o butan,1,ol andethoxyethane are 11.o/ and o/ respecti$ely&%xplain the di-erence& ns5er


%&' p.26(

Back

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New Way Chemistry for Hong Kong A-Level Book 3A#%

New Way Chemistry for Hong Kong A-Level 3A#%

% p (

There is an O group in butan717ol. Thus butan717ol molecules are

able to form hyrogen bons

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New Way Chemistry for Hong Kong A-Level Book 3A#1

New Way Chemistry for Hong Kong A-Level 3A#1

% p (

%xplain why propan,1,ol is soluble in water but

1,chloropropane is insoluble in water&

ns5erThe

O group of propan717ol molecules enables it to form

hyrogen bons

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% p (

,hich molecule 5ould have a higher boiling point&)'bromobutane or +'bromobutaneI ,hyI

ns5er17bromobutane

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% p (

1,/hlorobutane and 2,chloro,2,methylpropaneha$e the same molecular mass yet theirmelting points di-er& #he melting point o 1,chlorobutane is 312o/ while that o 2,chloro,2,methylpropane is 32.&1o/& %xplain the

di-erence&

ns5er

21., "actors #ffecting the $hysical $roperties of Organic Compouns%&' p.22(

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elting point is a measure of ho< efficient the molecules are pac=e

together in the soli state instea of Gust comparing the Ban er

WaalsF forces among molecules. ence melting point is a function of

the efficient pac=ing of molecules but not the contact surface area.

17Chlorobutane is a straight7chain molecule

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New Way Chemistry for Hong Kong A-Level Book 3A#

New Way Chemistry for Hong Kong A-Level 3A#

(a) What are the ma!or actors that a-ect thephysical properties o organic compounds?

ns5er%a( The physical properties of organic compouns

are mainly affecte by the structure of the

functional groups ipole moment of the

molecule the formation of hyrogen boning

bet

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New Way Chemistry for Hong Kong A-Level 3A#!

(b) #he melting point and boiling point opentane are310o/ and 4&o/ respecti$ely while themelting point and boiling point o 22,dimethylpropane are 31&5o/ and 5&o/

respecti$ely& 6ccount or the di-erence inmelting point and boiling point between thetwo isomers&

ns5er

21., "actors #ffecting the $hysical $roperties of Organic Compouns%&' p.2!(

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New Way Chemistry for Hong Kong A-Level Book 3A#"

New Way Chemistry for Hong Kong A-Level 3A#"

%b( $entane is a straight7chain molecule

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New Way Chemistry for Hong Kong A-Level Book 3A##

New Way Chemistry for Hong Kong A-Level 3A##

(c) Which molecule hexane or cyclohexanewould ha$e a higher melting point? %xplainyour answer&

ns5er


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New Way Chemistry for Hong Kong A-Level Book 3A#$

New Way Chemistry for Hong Kong A-Level 3A#$

%c( Cyclohe,ane has a higher melting point than he,ane. olecules

of cyclohe,ane are more spherical in shape an are pac=e more

eff iciently in the soli state. olecules of he,ane are linear in

shape an flattene so their pac=ing in the soli state is not

efficient. &ince e,tra energy is require to brea= o

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New Way Chemistry for Hong Kong A-Level Book 3A$%

New Way Chemistry for Hong Kong A-Level 3A$%

(d) 6rrange the ollowing molecules inincreasing order o boiling points& %xplainyour answer&

ns5er


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%( The boiling points increase in the orerHbutane I propanal I propan717ol

olecules of butane are non7polar. Their molecules are hel

together by

Ch21 (EE).ppt

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