*cl.

Lqk
r4S

V*a, sf-6dfq b *,d

k a"rw- b*d , t"lt,

.pcenJ

?r

globk

bwc{.

o,uhic./n.

dffial

-ks* g ""

h)ak {

ATluu&dr it'

744''/>/4/

. .

Homologous Series
General formula Chemical properties

same functional group

10.1 lntroduction to Organic Chemistry

b6*

svw!

Hi?ffr"r, l g,*1,
ilt_rn i rnt yrc ywlrlr

1fryr,u'"ry
Aqmc
ucYtt*'

Displayed Formula, Structr-l&llFormula, Molecular Formula, Ernpirical Formula, Skeletal Formula

*On paper

Nfaming

the compound * Nomenclature tdkarte,,'i,,:,,,,,

l

yclic or ring alkane

alkene
or ring alkene

Organic Reactions

'Unril,'Xllllo*n7of

4,

"r1 /

cr

!._

,'

r- r.*\ +o "'{rf {f u lla.,t-t e*rwCt'trc'"'l lt'vntct{a -\ * rsF '\nuil rt,"t'(' ))41% & ,

SrSarlic-rcffins are ctassified

Type of reagent being used ir a ffi 'tuffiF Uffi#

in

2Y4a blr
E

is beang used. ltE

is berr usd'

tettrt

G*d

\l\,tlat happen wtten the reaction is ovel trs been added- tlre r'-acti:*

rErffi.i*4

:3.elrrye

fe,ffi*fficedilwE@ts

. .

attracted to +ve eg. NH.. CN-.

cflrge{decErffi

sD'ia
-ilil@Iffiff-

Ott- Ct. Sr R-IIL ]r!o

t#tfire,

. de(asldefuiertsPecedtr@ilffi . atracled b regirs tf --{G dqEC*'Iot . eo. H*.8r. Cf. ilO"'- R

6 C*S

tb,rraltr
ard FbterolY{ic Fisston .
Organic reaclims invotve covalent bonds-

HeterolYtic fission

bre*irg

and formation of

breaking of a covalent bond both the electrons go to the same atom

Two ways of breaking covalent bonds:

1.

Homolytic fission

breaking of a covalent bond one electron goes to each of the atom form free radicals

f*tlf-q

du

n-$"*rb l;.o

'?*

&-

r4cftv{ Make sure You know all of ttese term

. . . . . . .
Molecular formula, empirical famt-da' displayed formula, skeletal formula Nucleophile Electrophile Free radicals Carbocation or carbonium ion Carbanion Homolytic fission Heterolytic fissaon Addition Subslttution Eliminahon Oxidation Reduction

sh.rctftf

hArif,

'EIrI"a-

/ /,C

----fr
t

-4

- z+hyt' 5-rue thyll'tEt*<<

;,e

B 4-Mhl _)_rkAth$z.4a

CI
L

li c--c-c-* It

.-L

C.

1C"

fi"

t-

- 3 -lve+hylfup+ana e+ryt - 4- ,t<rf,;rlfuxanz

dhlt

YtXAra:%* '#1
(1

'/ nr'G

) Structural lsomerism

Same molecular formula but different structural formula

1.

C5H12

'
3.

CuH,o C3H6O2

c3H8o

"On paper

_--__

\ \
D

tJ-o- tt
.
(2) Geometrical lsomerism

o
.t\.

-02.

Cis-trans isomerism C=C, cyclic compound It arises due to the restricted rotation of the I bond in the C=C double bond. lf the C=C bond is rotated, the n bond will break C.He
3.

os-butenelmciq , trans-buten-edioic @ilnslcwbot<yi( acid

acid

'

'i

cis-but-2-ene

cis-1.2-diiodocyclohexane trans-1.2-diiodocyctohexane trans-but-2-ene

CH3$HCH=CHCH,

, Q,Hr,'

r "' . ,'' '; r.:..

Example
Draw all structural formuJa and cis-trans isomerism for C.Hro.

Different phvsical properties

'.imemical
s)rnjt

cis: higherboiliog point trans: lower boiling pcint cis: polar molecule trans: non+ola moleeul

propertbs (but not identical)

react with same reagent, brrt at different rate

rr nul Sro.l
Optical lsomerism
a carbon which is bonded to or groups of atoms

a *ficrt( ilc
'1

$iwwt

in

Thalidomide \6no'tlt{'r

Eg, CH.CHCOOH .+ 2-hydroxypropanoic acid

OH
't

CH"-C<OOH
>R-uWn seo 1C=C
IS

t,z

\ ,/z'

,--"--"*r"o*Jt--..
chiral carbon

The thalidomide tragedy in the 196Os was caused by a drug that was prescribed to pregnant mothers to treal morning One of the enantiomers of thalidomide is a safe and effective medicine; unforlunately the other enantiomer is a powerful foetusdeformer.

f;Y^t57' +oi
d6y.V1t

have'
romd

t '

ct\

Mirror imaqe but non-suoerimoosable

Optical isomer have the same chemical & phvsical properties (same boiting point & melting point).

But, they are different only in the rotation of plane polarised liqht

b^q
f$e(hg

.
P

A pair of optical isomers is called enantiomer.

,r irrwrla
r+

equal _+--damoulrLof both +ve

Racemic mixture: is a mixture that contain & -ve enantiomers

*&1Eg(aaor(c*^e

,n&,W$ ffd

me

tuek 't{v

Number of stereoisomers = 2n
n = no. of

o tt
tl

-.
LV

chiralcentre {no. ot c=c

,:p,.}Zifl_.d,
t-Av"A

-'/

t/

@bl Br- -/ C-*

t4 /
Q'

1. CH.CH=CHCHCICH3

,/

-or

to,
i*s*/a$ir

(tt t{on*r
alox )

*a.'tS*

vet "\v''fi/ sll tralry ( hrt

f '. ot 0 (n
*

'{ ' nny**tr"(

Yda &"t-t .vfutic-^-{Q

4', rBY C:C ,-1arhl "l/, ."1' 1x ( c\unJacf

isonte r' s'u'

WY eH0
r>="-----T hn{t, b'nl
ff*np

10.2 Hydrocarbons
(ai
Alkane

(b) Alkene

(c) Arene

- benzene and methylbenzene (A2)

lntroduction

. . .

Saturated hydrocarbons = carbon-carbon single bond$, atFatu 6hain General formull CnH2n*2 suffix. -ane ' l

4rbg
Methane E
1.

Llr*

2.
J

Not.g$pfe

+ffiffiffi
1

with water (tak terlarut campur) Soluble in organic solvents (e.g. ether , CCI. or tetrachloromethane)

___

t_ Octane _ -_L_ Nonane

I I

Heptane

- M, - number of electrons - vdwf - melting point I - boiling point - volatility - density

T
1

in the molecule

D;;tl

----

I
I l

,,

effect of Brancnfrd As branching

(a) Votaritily I (b p. (b) Density

increases, I riir H l) i :,, i tn'-"-"n,

Exampte: CuHro (i)

I I isomers I
i I

cH:

Revision (Ghapter 3)

cu.

z_*"r,imrtan.
b.p: 28.C (iii)

cH3-cH2-cH2-cH2-cH,

/ / / ,,

As branching increases
surface area decreases so the surface areas in contact
so VdWf become weaker

so b.p.

pentane
b.p:

36'C

cHr-g-cH,
CHs

f"' t"

2,2-dimethylpropane b.p: I0"C

Chemical properties
Alkanes are generally unreactive towards polar or ionic reagents (e.g. Hri*Cl;-,

whv?

Nl.Off

ilrs#{s}e l'4ot+ inla(+wt , atom substitute (redac6)

ne Hratoms
.

al'il ark *rLaAert

'cmfl"ffion

..''OH-,,MnO.1-.'

alkanes are they rrave $ to react with reactive species e.g. H_, .-

LH+ +Cl2
UV

Jrohr

CH3CI + HCI
chtoromethane

.'".; .

;'

so?

CH.CI +CI2 .- CH2CI,+

dicloromelhane
UV trqhl

HCI

".'

@Y

CHrClr+Ct, *g116p, n ,",

lrichloromethane

CHCI.+CtrJ661o +

UV tioht

HCt

- {"rt

'+rPe 4
{o

ruacioq

diffaetttqfu

tetrachloromethane

. .

Mechanism: a series of steps to explain how the reaction occurs +W' +oilA'Ali:'iw There are 3 steps: (a) initiation (starting the reaction)
(b) propagation (helping the reaction to

if
i' Produce CO, and HrO C"H, + (x+Y /) Oz
i I I

q +hd Yaadtm ucl

_ Eg,
cllo +
2C,..

- co, + 21-grg

x COz + yl2 H2O

.,1

continue)

(c) termination (ending the reaction)

.Write

on paper

-Produce CO and HrO or C and H.O Eg CHo + 21, Oz.- CO + ZHzO or

CHo+6r*C+2HzO

Petrol vapour

aD{air

-o9*
2,2,4{rimethylpenlane) is much srnoother, mo-rg efficient f uels -and ler$s' likely. to cauS6
tns.ckilrgf Combusti,ort,cfbreiictido.ciiairf'ailTtS.fi6 1eg.

by electric spark Rroduce, exOlosive reaction

odd'\ 1

the pistons of the engine

chain alkane
-.

-isriitenArFffiffi{5Hd%ffi r'os6enfifnary -praobB8ffffit* - caosn6rftffihffiffi'd?ttrrft ft ffi i

Octane rating 2.2.4-lnmethylpentane is set at 100 and heptahe.at 0

P'nUt')

'fa:ar '3:..: .> r=,as:r3l .=r45.: l: a B.'-sz al - ' !iii:T=.h-.k-. i:re arrj !.a:!r

Petrol

-x**runffi *Taiffi

additives,@tv)

r-#{
.

- EtrB-..fft"#iffi"

cH

,"dfllh*gr
Cracking can be carried out br
(

aftttfirffirrraer@* 3 : ShE
.
usin&g&4y,t

'

Many countries phasing out the use of leaded petrol . Brarn damage, neurotoxin. nervous systeni

. . . .

lmportance of Cracking
To provide fuels, gasoline or petrol To produce alkenes, CnH2n (eg, C2H4, C3H6)

-- ,",*'* ,l nfiil
_: --tru

fr"fi

Cfgf

alkenes are useful to make polymers

To produce branched-chain hydrocarbons that provide gasoline of a high octane rating

Example
(a) C,rH2^ (b) C11H-4

-hp Ai*erre

-'

CoHra + C.Hu + Cr11o CnHro +

CrH,

po

ssrblr flll s

-1t

VvaaY lc\ttf- i'f ,g 1r\l -ncf c 9w\11 ,,no'ltf.^lt ( c, -cs n+ @as* a:rt- Ail.uP pndtrrr

c\

S"*

Mvr

+o drq,il cft (ch )

-l
-C

)
":a
.

l"rr1c- C=
H.C.
'f-^z

:= 1

. . '
(i)

lntroduction
Unsaturated hydrocarbon + C: C, carbon_ carbon double bond Generalformula: CnH2, -ffr d,r;lin alkene
Nomenclature:

But but-2-ene has 2 isomers

Cis:bqt-)-eal

u'

_"-(.

.LH.

\.. H"3"H

H\^

H^c, lrans . }(-yotp

u:n

_CH-

"r,

suffix: -ene CH3CH:CHCH(CH3)CH.

f-nnO{Uyl:Frr?
but-2-ene

Q: Why does cis-trans isomerism arise in alkenes? A: because of

(iD

i' cH3-c:cHcHg

RE,
Do you remember?

(i) (i')

Dier.res = 2 carbon-carbon double bond CH2:CH-CH:CHa hftq - | tZ -dieg

.
QlA

As the

rffiffiffi

Physical properties
in rhdQroil!il7ni

Cnr:g-6**Hz 2- mQthylbotta - lr}

CH.

- tfillnt

-the

molecutes become

ffiffi"

-numberofW
-lfflAhgtli
-lrnfihSBE&!fu.

.
(i)

Cycloalkenes

-u#us8il$m
<lu

O A (iD c6H,o O qcl e- cuxr.al

csHB

pznlen(

but, stightly lower than the because

offimfiffimffi

sPonding alkanes

Chemical properties
7 Combustion

J . Electrophilic

addition"_ halogenation \\. ..Hx 'i hydrogenation

\,,'H,o \X, (aq)

Eg,
-

Produce CO, and HrO C,H, + 11+1701 O,

C2Ho +

*,

CO, + v1ry1r6

16,

2COz+ 2HzO

i i;,-,
;, iOxidation . Addition polymerisation

Limited Or:
Produce CO and

Eg

FtrO or

CrHo+ 26, or

C and HrO

2CO + 2HzO

CrHo+6,-2C+2HzO

,l

.4

Wa-rut '.

*orfur nift
hir,1

tnltvt-

^n,1 " agP

*N l-{

trrl( g cnt* n-te"t (hrt"td Pdlt,oJ

wy
ttrtlq5s

4sc-t&d,

Dc'Jl a)vQ

+Ac'Arfln'tr

rtsry *

Ury,,+*

d$6ElectroPhilic Addition
Unsaturated hydrocarbons

ffi?f,Fjl+L:r:'--

-!

.@

addition reaction

ffi
type of reaction: electrophilic

'effifigffiF* 'SffiS{qstdr*effiffi* or "-'- " " "{rprB{ffsffirffiHrffie

.
Example:

. AJkenes =

\/, 7C:Ca+ X-Y

-?-P
XY

tl

Cll5f,ftlr+ ethene

|t, -#
18o.c

&E.d*
ethane

+ffi

ttl tu +V'l , hlJtr'rY'tr *:\ t?r lro{a\ C/WU\ v'uhrCh h^v0 d*bL
Exercise

(a)

Ni . CH"HH H ! "l I I ^..*2Hz Hear ' cH3-c:=c-c=c-cH3

Hydrogen halides, HX are:

Hydrogen chloride, HCI Hydrogen bromide, HBr Hydrogen iodide, Hl

(o)

*H,

;lBO"C

-watr{j F ftrtf
cccur

D*d
(a) CH,

tu4t
HCI ,ilT-,-, )CH3CH-CHCH3 l=rF.erature

rd

to

CH, + HBr

j.ffi;;p

(b). 9Hr-QH,

CHrCH=CHCH. +

Mechanism:

tt

I H

CI.

Br

Mechanism:

,H, =cHCt +
cH z-.cH cl

Hi -->
. cH^z-t)u 01
<-.+_,-

' [l'rt -'-

.,---------r-

,A

cnse|, c4= c{

cl-l

}+

fr74-+7 C}]qCH' (H-(tl(tb

/t j

-+

- :! cngctl-riZy,:X1'.'il,[ffiffir;;
/

lnalor-.4hp necha.hrllrt eu&F uucA

'Y'+)* fnda of {t/can tdny,

c rtsriet

#,5Xer +haa

T:ryAr na cla,tiJ>t

w oa/ ryrt e

HW Ynltrlo
(c)
CH3CH=CH,

ffi,, HBr-ffi",*;
ar.
cHrQHp-QH

g"*r, t-rrrl

propene
CH.CH= CH. +

nor ano propene produces z-oromopropane as the maror product and not 1-bromopropane. txptarn why rt is so.
Note:

,_oHfolloo,,"

' HBr-{oamcmperarr[-

why.Markovnlkov.s rule.applies. _explatn must know about --. ,.,,v,r uu carbocattons (or called carbonium ions). . .

B^efore

,-J]r#oo"n. (mi

il!ilP.r,,on

(or carbonium ion) is a carbon.tem with a pgsilrle

HH 7
primary (1') carbocation secondary (2.) carbocaton

sru)j W\^rVrvfliP4f

(c, joinedro !c-.j:ined lo , .utTi,rjlu) 2 carbon arom) 4 S-WanyoY"e accotoliq fu

tertiary (3.) carbocation s

ia,jo"il;';
""in
r

ffi

rt"*f

*s*
H 1'carbocation
unstable
, C2Hs, C3H7 etc.) are

,t
Q: The reaction between..HB: and,prqggne

produces 2-bromopropane as tf,e mrio, product and not 1-bromoDrooane.

Explain why it is

so. uV s*"tr;tt1 t c

ca*tdh 1"

ufr,n

czHs

rvl

^"-r.*E+C5H1r 2" carbocation 3" carbocation ?o

^..M^^+r^-

H-5S-eH, n-E*at.
locarbocation

9H.

l+u atYll n@? c w;tdolb o so 1+ istuas{ fubV

'Umnnhnm
becornl 9Pecrzs

pt^t\* e-

+"

NVr

,
- . 3 >L )l
2-bromopropane

-,l

.ln 1W

'-n:''

Carborattot

1t \q'r$c1sfitt.

cL,-/=-c', +H-Dr+

formation of 2" carbocation

n41-

*:er
major product is 2-bromopropane

2' 2^yhcrltan
=

gt an

tnhlt

-c
I

M ;s hll Lt Acondrthd uvbo ca*ir,l W rnrYq !,nwyjiicall slrJy'4- {tqn lyfvlct1|,oo! which rnoY\ ttwqltlirulll 6as hooqld vz "6rnol iI W addr+,urr 6as lta o+nar n)*fl,ryurrd, ancl so kss Athvaltott e uctT

(rht

'nud"d )

-ttLdg shou$

'r,hai allcyl

+t0 *vqt3 - ,ui'gai

6 e1 c{l- |u{u {'staUiltP 4mug '"onv'^i"Y) I0v1 ay ovnolt$ z

wtt BeatrtP 4t^ij is

4'-L

co

iC
rafiafi $

,mad ,Y ,t,.,'l

rb $) C, mt /,wa[Hs
(a)

t A.'lcfi-l:tN 'f 6J"1ngu, A,,,l,c/p prul .', l, br# $rrr,"S^ 4^li.t"

,

{( 9r*

_**^@g

.f,i3?.i#,vr,f1d?-r
HCt room
-

dw-

CH.CHTCH=CHz +

rrlrtemperature

Callol

l- chtonilftctnL 1t cbcH,e - c

' { *"1 *{"q!-!#,i)

arba
'

&t

ll

Q q?ve a4r

^fir"
'

Tnrlt cl

*.G;:'
Exercise
(a)

. Catalyst:ffi . Condition:ffi|{FffiF,
.
Follow Markovnikoffs rule

ReasentcntHt[lhF.

9H:hl H H I -l I I H.C-C:ftQ-c-H

2HrO 3oo"c,60;

H:PO.

,t:a1'' HHIi
+

HHH-Poo-IT
+

H-oH

*".

uo",, H_ c _c

industrial process to manufacture ethanol

Mechanism:

i=",, i,,:8**,*h^ 9r,

(
{,1

--'-r) tnf(/
V

{'\

paitred a.
,6

iliq,*:, r( v\r,r-\n i''"1"'{

.'l' 'fi Prnn04 M a,lt'l 'nl ^gr1\1vu

Lmn04 ndt

olccrrc

Reagent:

' k*n&*mWwWffiiryryr6'6
'r
CHr=CH, + 2Br2 + HrO

&e {mJ*

ffiqp.f,f! +

ffiffi ffi,

;fii;36;

Gcickftr:t
(aatltfie"(

%
.__.

KrCrrO_, / H2SO4

Cold alkaline KMnO. Hot acidified KMnO

'

g'i1

A *'ilcl

Wdvt1(i"

.Observation:@
i

@ ..Condition:
ar,,

ti$x+$ffiW}ffieffimnW lan x. t
',^r',ct,fte

ryffiBrt@
sifte$frjiMflJn

nttFfutir rrol+Nt#i;ki ')=o + o=.{

ru,o, .:\=o + o*{ :
I

f,fiaaA4

cH,=cH,wfl#;,;,,;

trs#k.

:( or+ lH,o
((o \

l+

r,rSg K, (r-C.,

ThT

lvit

-rl

4 r,,,,hirk r^1|r^ck *lc

i

C ( ha-ug *. br,u,J )
bC

r;i

rnc(cl C- al'i{

t( tt,-(

g-{*

rl
B
i,
i

rl

il

ll

-^

fUl- cH' -c\

.tS Q a..qk +o n'\!dw- h'dcll'o'

..1 O=C\H

ff.rux,"uVtr
6rq cr'.ru9'

Question
Predict the products \r/hen each of the foltowing compound is treated.with hot and concentrated acidified KM;O4 s;parately. 1. CH,CH=CH, 2, CH,CH=CHCH, 3 (CH,)rC=CHCH,
(CH,)2C=C(CH3):

:y"n'nnl cHl z. r-Y't

sr.\ " \l'

f *,r, lo -rlra

Addition polymerisation
Product poly(atkene)
,/
._._ _-_/

,i \,------ ---\-.\ , ,
.,

4. Addition Polymerisation

,I / -_ tsunner orscuss In . Chapler 10 o

\ s.i \ iorsmaYwlre mdmb (po'hd) ./

moteales (morcnE

hvotuedjoiningtggethe,

_r3ry::"1:1._

--''

-----.
H

H. H'

-H Cj-..C H

,/\

-C-C H H, po$efrenep
tpoallrnerl

ethene (monomer)

Exercise
Propene undergoes addition potymerisation to form poly(propene).

t' Ctl.-C = C4>

f
-L

rf
-

f
I I

*-t il+

bual_

:t1

rO jF 5l +-t -.# I ilr!

fr

-. sil

ll

-m
il{

rE6

r[i

sffi

EilI

ll
tr
m

cl

GJJ
r[

--l

--

:5 U4r crq -"qJ .

:a< sc)
q)
l-P

er-

\-r, c

ii

*.tt \r

o .t
-v

%=

t-E

O 4

\l

o+lqr
1O
t)'n

,;'>
q^

,ai\

.{.";"

.0

;rnxa

u
^l

u at+'Y.qwcD

''.ta@f ^-k&',n
s

P \,) 6(
av L)
td)

\,/

o^')

"TCr

-F r'f

5 -t-s

sd

d-6 =E

=( (t'

tr :'
{1, -,L att

.Y ,4 =5: dCt) L:
qJ

-a-

E)

.tLl

s)

-G 3

E {t c
a--'l
r.r-

L
CA (J =,
t
l

.t

ei

G.,

T q-\

,(,o

<. \) \)

(J

=l 5l vf

=]l
L
CCj

.<.

<l -l

s4

*-t-

<sB

SE 'EE

B;f, 6
=P t)

i( -\b

s--,

(iF

t.^S :s

s_s

fJ -g .J,

g.Q
rJ

i")*r,
-fb!
IJU
4J

OO rl
a

%Ai
191-led

r\

o,

ffii13
l{aloqcno*ton

} k

'3
>r-

u&t;r,,
d: ifl
\cl-t5
I

5-d
co

!L d-

!\ U-o\
'QQ

o .t
+-{ (J

= i vl .16

l-o.

2I

d{1" I o.t -5t s-

std lo
-cI

:
L
_l_ (;---c

rl TL r! q-,vrl

-T

t-il

^) t)
_)-

-,o

__d + + --l_

(J- o

<6:>

a .a
,= 5
C<>
LJ

-I-

--|-r \J
I

O
-"1c-{ = !S,

a
a."t

o
J

O,
J.

a-rJ-

-t-

a Ua c-(

'-F a '1 c
-.1"-

+
J-

a
-J-

;l a

3(

d g

l(-+-rS)

c)

It
A

-tU q/
IJJ

to.C

fl

-U
JIuoo r.

sT c)

t\

*d
B-i
2

dlu
,16o
-.!

e
c)
U

=!(

5 -lo +\r 5to

-!D -.L
,*.)

{f,s
"64 B \-' _9
-L

<

s) v

H*

E{'
t.t

J-

cF{i

LAt
cqr-,{

-,r S2o

Canbrrn + dt"atz&

ly1.A"d,{,4 +to

1'llffi
uoy,lch t^NQ

!" s^rLacrfi^

3'c*rbcccrt.ar,

* *b ry -l i, l'tA

u ,l

/\l L]-

/r.-

L _C{

>.

.
1

Halogenoatfr@
Haloqenoalkanes (alkvf halidesl

0.3 Halogen Derivativds

(a) Hatogenoatkanes (b) Halogenoarenes

alaM
AS BVa,l h s UlAl

R-X

R:

arkyrnrouolT*._,

c,Hu_

X, F,Ct, Br,

etc-

-=GP-E

cHr_cr[1*

J-6romopro

(og. hc

t(wt7) ir dft^d,oJ dirlclf *rbwtnt-rifi

. Halogenoalkanes.rffi

'

Halogenoareqes (ary hatides]

Ar-X

Ar:aryrsmup=

@*

o,

,T%'",ir":ifl

$ff.,1i;|,1*: tsi i f

'1,n

.":.:! :,

il ;:;:r;-;; ;; .*
i::ltffi

chlorobenzene

Z-bromomethylbenzene lu

atwalswr^O Preparation.r@

nt ffi
\/
+ Br2

dAocaJ'uPd-

tralogol,oalla,v lLt l'J t -rr lc , >4 arqi.alld,,a

s't

7u

' ';'

\ /
'

lr )

-*r---> cH.cHrBr -cHecla type of reaction: free radical substitut on

type or re'acti"",

2. CHr=gg, + HBr ',

Chemical Reactions

*."*i,,,3]ill;i.
.

'

f}t^l:oFr --.3ft+-+ rype, of reaction

ln 14 gt,tt hi';ul','.$t, nl9'fuM ri44Ffirlru

Ca"

cH3cH2cr : nucteophitic .rOr,,,,Ji,on

al'l"t arJ

"t+ffi*

axcapt

b"y{

co'npn^nd

sd.j lnv5l"t
\
t^dftr0Lqt^/
o.

.1

$
t

-.

l.l

ol,ro[e.ot^n nuaoiPvtttic
__-Chemical reactions
_ 9dbstiruhon '_!-

&d[f'ry
ste!)_ -. -

i;----

- ^ -- =-, oryz

1ii.i,.r-",J,i",rate deiermiorng step

_-.!sLoy

bimolecular nucleophilic substitution 'l' halogenoalkane one step reachon Ntts substitution

< t_::L "\'

,/

lnvotve

I mole@le

rn

Nucleophilic Substitution

raledeterminingstep

unimotecular nucjeopf,ilrc substitulion 3" halogenoalkane 2 steps reaction

Q: IMtat about 2" A: S^,1

__{slowstep)_

.--'

1.

Alkaline Hydrolysis

. Reagent a$leorrs lrtaOHorKOH . Condition: heat or reflux . Product: alotrol (Br out, OH in)

Reaction of bromoethane

Example,

(a) CH.CHTBT +

NaOH

'"1i_.

mechanism:
" Write on paper

CH.CHTOH + NaBr ethanol

What is reflux? of time to occur . The reagents must be heated for a long time . A reflux apparatus is used . Diagram

Oiganic reactions take a lot

'

Q: Why 1' halogenoalkane does not follow S"1 mechanism?

Summary

'

Sr1 mechanism for 1. halogenoalkane involve the formation of a relatively unstable . f Decreasing stability of carbocatiofls: ""rUo""iiin"" 3"> 2">11
H

1' halogenoalkane: S*2

and S*2 (not in

. 2' halogenoalkane: Both S*1

syllabus)

RCH2X

R--C' I

X_

. 3' halogenoalkane: S*1

H 1' carbocation (less stabte)

"5,^n

^drrt"'u@Go.,u)ct"'*akt$ MA{oJ *q6\uo a |nduQ +rtfu /A)

trn^

,*n,
ia^

ct tr l"sd prorluo V ian po"t\r/\ sl\**h 7 yfr aLu

1
?

o,q-e

DP

&

cN

2.
$neral Example:

Formation of primary Amines

What is an amine
formuta:

R-NH, (R: alkyl group, CnHrn*,) CH3-NH2 methylamine CH3-CH2-NH2 ethylamine

ethanol)

cHr-cHr-Br + NHs

Example -!9?!1,*" -. cHs-cHz-NH: + HBr bromoethane seared

ethylamine

working:

. . .

Reagent: excess concentraled NH3 solution (in Condition: heat in a sealed tube (because NH. is
volatite)

crlr-f

-'ts' -

il

til-

Product: 1o amine X aiom is substituted by amine group, _NH,

NH.: nucleophile Type of reaction: nucleophilic substitution

3.

Formation

offfiu
__-?-

reflux . Product:nitrile /E{9rHk, . Example:

'

as a Condition: heat or

Reagent KCN in ethanol (Note: ethanolact

Remember
The nitrile is useful:

solvent)

,Yt-t

-i-r'+kNffi;Z*u-t
Flr1a
(tt-nfu1

&e,tol

# ,/

,U
fl 'l

1. lt is used to ihcrease

carbgxylic acid.
4,...

the length of the carbon chain (add one carbon). lt'gan be converted to an amine or

.,,
.

'-

'

,
.-,

't'

,I

...

RCN

_ ''can ff[T[t?"',',
(i)
(ii)

can be reduced by lithium tithium aluminium'hvOriJ" in

l"amines

be hydrolysed by

i.C-_ A cll

refrux

-:
C

carboxylic acid carboxylic acid

dituted acid to form

dituted atkati to form satt of

oo!lR@

' .

1.
Product: alkene

Elimination of HBr

Reagenl: KOH in ethanot or NaOH in ethanot {Note: ethanot act as a solvent)

Condition heat or reflux

Other reactions

+NaoHffit WL=L*^
in
e'lhqnol

+ NaB.

OH act as base NOT nucteophile

... accepts proton readily

HBr is etiminated from

ffiglife&#rmr.

10he

,1

+rLro

efl-

ay'jeont C .4ufi
A rt'.. c=c + U:9

uv_.

./

/y,

t-lt nntrto,f*rl

,-/

Relative Strength of the

C-X Bond

Note. C-X means C-F, C-Cl, C-Br, C_l This can be sown by adding aqueous /l AgNO. (silver nitrate) to the halogenoa/kane
The following are the

observations

\,

3. Tfrese reacfirrs recaledhydofsrs lln

4C-X bond is broken. Conclusion: lncreasing orderof bond strength:

C-l <C-Br<C-Cl<C_F weak very str6ng easy to break very hard to bre*
Decreasing order of bond length: very

Readiuity of CFC's uses and afus on ozone layer

c_-l> c_Br long

>

C_cl

> c_F very shod

r:ii '

l*41

l._:. :

.... ,a'

,S*rii,::iii.,:l

' .

CFC's are chlorofluorocarbons. They contain Cl, F, C {and also H}.

..k 1.
2. .

Ecanole:

;e'i- rZffi $w\ $Vw''rd

cc,2F2

They persist in the atmosphere for a long tirne. They undergo photochemical reaction Yuilh omne (O.) to form oxygen (O2)-

,|E,
-

lSfg --'

;"4^o

20.

- Refrigetant (air-conditioner. fridges) - Cleaning agent

Aerosol propellant

.
$cause thev are inert (strong C-X bonds = unreactive), iolatile, stable, non-flammable

so they cause depletion or thinning of the 03layer. As a result, more U.V. light reaches the earth" This will cause (i) crop damage (ii) skin cancer, cataracts (eyes problems), malfunction of the immune system in humans

36,

To overcome: use hydrofluorocarbons (CF,CHTF)

or fluorocarbons (CrFu)

Bplrfii't*+

rY

L s
4'

tr
1'

L (fl ('
=?

+c-.-.-r-_ .aa

(f

^A

7
{ \) T. d t r\q: ><<n '<
1 '- +',\ \ trl\

O
l\

ns
%-

-s+ -!.o dSYS *,C

L] .v-r cY _:: )

\,

\J

\J .f)
J-\

iG rY-+<\-.-;+ ;-Y ;.-Y e" \-t'"

L
.(-l

'-T'

v
\r-?
-S, l.{

\.-^ \ ,J

+r-l

) o\ /
tv

\, rr\ :\
\

\\, \,

^/ (3\ .+a \\z-i 7aZ

.a$

= Z.

,?
m
= O
j-

T (, .T
U
\\t

e v
.l

T z

rt

4
li

(J =tr-

'?^nk ''t' d E-,*aa,'+.,\F

\J
ete,&D

L - Jn'l

-i

i+
p

\-)

,t'1 ,gh *

i\fi\tt"

:tr "1 L] -l

ffi: !4

w
k*d

I g
-6

r10t* u' @ br,

)F

-E
.a,
<> 6

ru

ct

?4,

U., H=' / I-lc[

o
5 C

-3 q,

5
-_:!t ,)

Hydro lye

/ rs -

\-, ci <
3io
I
a)

.:6
t/^i c\./
t
I

z 6
T
rl
c*-)

'E & o

19

(J,

:+l dl
-l

"a\'U ;4\2-\o '^.

e -\

-Y\Lh

-- \ -;<-\ ur,,\.2* --<- \'

_-l
t-t

eii ('!

I
I

__.t o --l(-,i
a

I{

-\

_t <-i lvr
I

I t

-tsc
l,^ .U

\ .{/

=-

Z
j

q-i^, *i
1

+'T

-.

-\

'i- ;!t / .=t)

U!r.1
v

U,

*or, vL kd
ry
$
orf

/tT siufu' %
+h,t

, .{ s^ro\ rnu$fn.qt$ alLuvrt UasW 6v\i, tg L C ?

bh*

C;1,

erL

ol

hor;l

!. 6 r"
,trtaffi$iJ,

tH

{h*')
. .

''s

MY tuHt'*l
lntroduction .'
-OH (hydroxyt groupi

9-P'enYldt"anol
4havr alUnru

Functional group:

U(Up hqh"

AVaurt

10.4 Hydroxy Compounds

?_ttt

+uoffi,lfui {tanl

\h,gtnty Yfiar nalt,-tt" ic ulo'^-*

anol I atiohatic{ cH.-cH=cH-an f 'Peng -t -o i-;ij1c;;;;,-6H e+han4 - il e -cli

I

Aliphatic alcohol: CnH2n*zO (i)

alcohol:

/CnH*-n,
,

6t1

,f\

ol,

cH3oH

ryrg{h

(SeCULBJa

+ro-oH

OH

?*r+ )
.;
-OH not at.taghe*di{stlyl
tqi.the:

aromatic

l
!

cyclohexanol

b'efizehel'
n66

'

it nt leart ow f
i3

fq hdw

&lbrfltr aJ

$v -t)lt

at\c^dn -to Q iS n^lteJ C,

Physical Properties

(ia) phenol: -OH group attached directly to the benzene ring

$ t" ^"Fz
J'41,(6r,

dnonkl

usa

p, phenol &"' 6oH

t.Gl

1. Volatility
Aliphatic alcohols, s 12C and lower aryl alcohol + (colourless) liquid at room temperature

e-rneftyllhen.)
CH;C-OH
cHrcH3

1".

2",3"

alcohol

W,
ol..

CHr+C-|-OH CH3-C-OH

f''
rl^.

?''

p (1G;2H)'
lo

H (2C,1H)
n,h

(3C, no H)

r{c((.-) S

*t rvt c
I

<tcohol J'atcchol

3'atcoho

,dlacL tl

altohil

6n {,nn \*rtr

boiT

. -

Lower me?nbers of alcohols soluble in water Because ot hydrogen bonds with the water molecules

H-o.H-.o
water.

f _6.-'5-1'6'",'; I
H

. -However, sotubility I with'fi[t?lilll[lllttulfliltlm .. alcohol with long

. . BE[Graffihnfl|ff

carbon backbone is irnmiscible with

(more hydrocarbon-tike] As the chain of hydrocarbon I, hydrophobic effect T . This reduces the hydrophalic effect of the OH group

'Mo@-

fuxrc-

ttte

ao,.it,.

?tc ,,nSffi-*tr"'
Ct-{

1' Cl
-

cH, Ct-lt C$

h,ad,oph"6rc e#ert

ii

E
f-a
da*or

0q

ilfr,t",hlids^l fnaroh

r/

*.ritof
L.\'J

2rt3

] .r-lt n. "a 1. 2.

&t,cA X1r,:'*'?!;,i1',\1' t {' la(

k\

\ 's,.:iuhLr <.r\lt rhLl >\!r'r'/v

t!'t = (4 ,rJ, c;l I ; ,.- t; t'l*-i iitlli cq t rrr rtt.(l-l ,Ctl,C *

u'

/L'c

i* :*,;i.J, i,i*'Y^,=' i =\ -- r}-rt lO* o4 , L' i

" 43
CH"CH"OH
gr,'
i

Uses of Alcohols
Fuel Methanol, ethanol & ProPanol grease for = as solvents Paint' 3. Organic solvent

1.
'

\il' 4' ;^'I+ * ;''rl'ffi

CHr=CH, +

HrO -;'!?:- --

rit' roa'tt "t

{y

z lrtr 'le

4. Cosmetic industrY 5. Drugs. cough mixture

c.H,2o"
glucose

;i;.,=- - 2cHSGid+'

2co"

filt

'+ \Yrr{ I (-l ' c\

1'
Chemical Reactions of Alcohols
1 2 3 4 5
Combustion Substitution to give halogenoalkane Reaction with Na metal Oxidation H20) Dehydration to alkenes (elimrnate

Combustion

Produce

co'

+ 1.1'6

. Eg, . .
-

CH3CH2OH + 3Oz

'2CO,

+ 311'9

Burnt in excess of air

ethanol burns with'palg{#}816{fitilt'

Burnt in limited suPPlY of air burns with ye{lr$d''f'&46rc and sowrers6tt'

,tt,i'-4

AJ

' i1-i {

i}{*tt(,,'. {+ ts,t' '14 tl.\' llr*t lt n'l {t{ rr'u k JExf Frr rtld blr r

z5nttitution
-

to give halogenoalkane
oY

(a) With HX (hydroqen halide)

Hase* .]'oro proou." Hx

qlscenl{df;s Alcoholrs d\$e.d+q# NaX and

prs,.fi$o-,-ffi7, Na H$0* + HBr * Gt:cHr br * 4,o

",iu*ro,
further However. some of HBr will undergo

iit f o w"prre CF\Ct'lrBL from ethanol

VX

,t nll
l{,''-'
-f

tf
*-,

1! ilt' ,rril (

fr-.ffi eTfiif irj'"lt|.usuo

whitt fi^rrt

J;'::H;'"
Observation

- br, + sc, +)H,c

rffi$f*tftffdrire
bfFtst 6ird Er6'

"T[f

'on

-"

Obsert'ation

:.:,:i::'-l

t H-C

* rg"- -> Br: + 'e' -> Sij J:a t u-_-oO, -n H+ + 9e'

+
.16r-

*
i

tt

oldtetl .A,- {f-' ; is d,.{att + -

Lry{+ (f,r,\ *(Svi'+

oir 4{fd

.;,"

+fl'o b,-+ sq

)r,ur,,

", w' {T

b}}'osfl'

x' +J
H1

4 swtgt |firyf
in ro(r^ '.

sr^or^tot hala,tt

; I wh\) {i * ti ftr5* y, ry"n'#f

nD
blt^cP

ct tu

nq,S:$- . ,r. d *:7,'

,

flu1\, ra5 tutve ' *)L lea

tflf , /7
(otl +

\"t HE*r

'vo Tvtrp4

fut'l-

ctu*t1'

(iii) To prepare CH3CH

qu l,it'

(b) With PXJPS$ 3CH3cH2oH

PBh eL)-=-{j,*tl,ffi

-tt^fr
)
vtrt)

)"1/,p

Cannot prepare Hl by heating Nal (s) with

concentrated HrS%J

Because Hl is readily oxidised by concentrated

HrSOo to

",\\

. Should use H.PO.

2Nat + steamy fumes cH3cH2oH +

l,

I(n sho*ld *ory sliShll bfiu* alcohE '(c) With Pclr.Ohggphgous (V) chtqride) CH3CH2OH + PCIs -e Cn.CnrCt+ poqlir,! HCI

'

* pct.qqgcH.CH,ct

(-t)

'

\L)'

H3P,Q4-

l\aq ft3\

Hl* cllldtl

H.r

(5) %t"r*y , viulryrtr {xn *ifii, '? .i;l qtodqco el6hd 4 Hc) 6*s
?Xezup2p

;hstecd

qsrlj ?Bb ,i+u-orl

n4 o-ntu. r w"l'fwywru* * fu12"

Exercise rf[1 *H: + Hct (J)
.. t

*3}7-++l

(d)

with socl, (thionil chroride)

i";itifu'*
sor# -"#

l-

cHrcHCH?cH, +

CH3cti2oH + Soclz

Cn.cijzo *

dH6alcoh6l

HBr-CH-iCl'{-61f

$r

.,l,1oalbo4

Observation: steamy. fumes of HCI (g)

Note: This is a good method to prepare halogenoatkanes, better than PCl. or pClu

etc. Why? Because the unwanted products are gases (SO, and HCI) willbe evolved from the solution.

4. ,
5.

I
d'9*
+ pt,

+
PCt5

r + tl, [D,

roor+ rctr

C}),cl + Plclj Hct Q)

HO-CH2-CH2-OH

C)- C4 LCll;Ct +Pb

+Hct rJ)

4 c*qlatut t.i\9 tlF

,.s\

"

,t,tfra&

{p

a*rdtfl

cHl c*Y

Altrtl q"tir

t -ftrnru/o"

$rwd

3.
.

Reaction with Na
ane & alkene are rnen lowards Na

.
. .

4.
R

Produce H, gas

ea genJ.-a-cidifi ed

xnano.fo)

CH.CHTOH + Na

CH

%H,
u

[v$

Oxidatioor KrCrror\Xi/cioineo

. observation: sodium

' t'"'31if"".r.
OH

effervescence of Hr(g)","'-'Ji:L:t::lli,u evolved

Condition: heat or reflux Observation: orElRge colour of CrrOr2-tum green (or purple colour of MnOo-is

+ Na
CH.OH

6 *
q$$uv
acrd

+Na*
a\co\n6\

* *.11i1; + /,H, d
8,
'tg

bt*C+furcor c.4S

'o

fl+,

fnscrt,AHku)

'qlor,ol

ol/*

v\UtV

tifl{f

frvrl

&ery* "y'

Q coH I'Ut'*t 4 rtndtsni 7"4t'{f

\

t,^*n ^rtr lr, X J alclo tgol $.,vratb

J/X
ro^,
#,11"*u"' . CH@

al z,l)4, o.l-,
iAuo ,l

\
To distinguish 1', 2", 3" alcohol
1

1*

Veh4'-. Presence o,

:-: Oei.{-\ RCHo Dsti!..ff f ---"_

to

" alcohol -,-

[o] - abehyde ;

lo]

carboxytic acid

CH3cH2oH *

zfol

+ l-i2o

RCooH
C

carboxylic acjds js indtcated by effervescence ot adding of NarCOi (See carborylrc actd & derivalrves)

O. on tne

lr ,,oln\,

2.
-

arcohor

for

k.ton

"{ __._____

:B}g?["j:T:.;:::l,j:.,

m.Fc'o,ffio
laraenyoel

ffihE. ,", JH, ilJ:1iffiffi:fi,t"' ( T'5' alcohot etiliZl

1' CHTCHCH3
+

Presence ol ketone rs indicaled by orange ppt on the adding of 2,r4-dinitrophenythydrazine (Brady's reagent) (See carbonyt compds;

..-YIEE

oH 2' alcohol
(CH3)3C(OH) *
3"

[oJ

rM"9.1F,,9_o.

Gflux

.",.?*anr* Hro o
no reaction

.propanone (ketone)

alCOhOl

[O]__1f9r,119r
rertur

, -"i;:'"'
. #:\t]"r
HO

CH-CHCH.OH

* ztor I!'o{E!o.-CH: C!

Exercise

, 'Uf"J"'-,o, H,j'*,*o
+

(,, t H,0
'4

,-o

.
.

5.

Dehydration to Alkenes (Eliminate l"lro) Reagent (i) excess eoncentrated HrSOo or

4o1

- rM.o!.H,s9.-

(ii) concentrated (iii) heat with Atro, (iv) heat withceramic Condition: heat at 180"C

H3pO4 |, l$N

or or

X ltsA

5.

H+6ffip4;,-.",drryKyn% eflu\
,- l* o,
CH.

l-I

,( -os

CH,CH..

-'"iil8ti8r'--i_:::_ry311-1'AIE?!HE^,.,"'
H.pO. 3OO.CbOatm

z1o1 -U-no;l!-,-.
I
bubbtedthroughdlr?
NaOH to

_"*:X;cH,oH',,oqffi[. ^ldthgt" 3. no u't

-t H"0

----___,

+:,

"=##f9

cn,=c

-.-... .. ._,oss;ue acid_3pt4_2

.moE a,

H,5iiff=
-(

nhlc

., or,r\

#(

{{^0
no

@rloon 6, h,{

a${,acl"

u9%

tho s<essl.i+ ^ na ^.- o 7 F. " Esterification

T . Reagent:.ctrboxylic acid . Condition: fieat or reflux with small amontd

H=Cn@{malor produd}
2 alkyl group

concentrdted F|2SO4 1as eataly Product: ester (sweet

act as catalyst

'

eqlm shift

..

cartoriatoms

Dftydation tends to produce alkenes wlth the llghCst nmberqf alkvl group that are attached to the uniaturated ._...:.t"'

Ro@
CatDolylrc

1. "=c

n'fl

,- _)

actd alcohol

#g+-

RCooF
esler

'[sf(a t^m

lf thq u.tdrr ^lhfl

?por^f

.#

%{
c{'gt ?*?$\

y aqk oZ4 f< a?x , i.\

qsr^

'

rLC

* V+ :,|akmt-'b, Lt
o,

*e1'61i t<- fTo S .tr-e rl'o.

>pt-t-a'(

Rxct4,

Exercise

Uffii::X"

products that are rormed rrom the rorowins

*-16,
2
Write equa!\on to form (')

cHr-8.-acHzcHl
o
ll

#;5=Ll

(ii) ,, cH3o_c_GH-CH] n

grL-ocff

cFr:

l' Ct-Q- !*-+-41'cu'Ctl3

ln, cil,Cfi,
Cll

s)

cu,

-nro "\04

c11, CH: dH

f-r
*t/

Fl

tl') qrurt

t e,l, *-ei,l
or

i4s J
*i I i 4/'\
"1

Ciq
i

t-iN
rl

tril@t

E;lii,(\.51*, 1' r4 l'-l .u, lH' L cL() *-J

0

^HY'l

tl\ Fl -/

rr
I

L*ru(x f
Flr

u,n,lo

alft''h{l

,o1

n 1 *tunr- R_i._F,-c Lof \ cH, !. _ )p.J,- cq,L"\n . f? - <(,, i..+ -\&t I

(:yt

,ucH,_l
i

cA.Ul

r [of =>
h,,

"l.t-t

,'1, -Y.I.r -od

T iAs
i{

=_o-

*hl l'g"kdt*f
^/ L
_",{

6!
ri

t tlodl, -dt - (4,0H * )&J -+ -&', - '-''

')-r' c!:

,, H'o
5

/\

C'o
I

,f

rii

t:

:-\ \J

qr

,-

ri

b'

+"

.l O

t
\
\

5 tP

u- "/q$ \:v \3 ) \JLt- o !t:F r', $:o

'{-"o

6 T

L
r{

Tr-

Orl T

\.0

at. o
lq

"*.q $r$$

\JI

.n

\Jh

.-,

(./'15
.2, l__O

l,g t-{-

U
O' oNcfl
J_
'
rt1

g
q
L_

)- 14

'$tffia*n
'4r., -

Lo,.

ule

*\u
F] rl LJ - .fl

\,-"9 *arZ\
T O= 11
--I- t-

=E
<)
l-

g)rYm,
>i
.5

Nqot

:r U

O .1
--J-

-c o
\,)

s,

& e{
:b
-C{

To
U

\-/ rq

-lr(J'

.r H'o{'reSh'
il

'
a\

T \J

.{

_r&. \ |
bl
,.-,[

z_

'o.1
U 'Fn -) \

+4

5>

'1

=E rl

bt
T U .l )()
I

5C
o

v\

f!

a o: \J

o I \) - g
cq
la

+
j-o

+ 3i t-

'= ,c

ql

^flj,b =^ oa, *v qt

""d{rj"*"

+-\3+

-l-l* -t -

E 3,.--0

tr=D

,{l .l . o 'A, rt -:, Yt =

U.

__5 )-

\l-,

-t-

+
-l '-'t-

, .<
.+ (,t ts, .+6/
Ln

s,

.<'
at

ez
L

--l x o

:r O
U
'----

LJ

.4

\) ,rl, o,

LJ

/1
p1,ot-l

vfrvt , tr/ .,

>hoxanfl

pttonyy ma-than

ht

9-

l'

alcoho

:Tr: VepaW .3"

Cnlcv-ooRanp

HCI >CH"-C-cl +

r/,

:@uruw

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t
I
I

,f",t:!,il

?*!

P,,:*

""O

,( fucu,ry ltighly
* lnlern6/gC, {a,
-I

ptar

4,,; d -{+ tc,j

tx r!'',r:it
.'.f t)-'
a

hdnaen
7_-

r'r'5.

,'.

--,

l-e

J )ctu 9t -

natt

r,*T
'-

- ) -Lr--rJ

4/

* tI*rwu, qrc
Sol"btltf

r';a* 747-ir - '

iv't6iq4,,'a

:"

-,i :; :H,:. *. kcaqsa r( focczu l6s tt 6 -

^*+h

-lhe alccl,ro)

bero*n

?nsolubfu

lvlora {H grcuf

, rnlre Cubtc (ethano-l)-d,cr }

fu"c oat
cJtz

tw

c6l"l
kMna+

\xidaticn

Nucl

ili

3u

ihrtion
*"C I vlJwt IsvI I I \- "2

7YtAc,Sl

DF

Wn

CccLtr

t4

+W absw ct

crucibk Aeaw clarL

HX

halidt

rdlq\ t;rlh
HX

KX

^irfh

Canssn+rqtit,

@naf"EEEEEI

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t t Lt/ -r

ruLJ-@Q

q{cfhdl

't"lo hv$y

oxidrJ

$ a'*4''bdffi,
. HrSo+.

fuaus

em,'HrSa*

uidtyl

No:......... Date:

C.A^

be U,&r.Z

oo<t

, \JJ,

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Vteqw gliqlrilV hqAncarhvl cry-V-v ' PC{q ' ntl wqta ' p h< /Plt

*E ry

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ad

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Wa c+i

on

Tn raau l,- fnduA

cJouc]

ftC'( q^r

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LX/', "'-J.\7/',

IJ a qdncl rtrtylhool {0

PruMrL

haloMttoqltaov fu-HUl*W'

&.c

cli

qtu fl&eoe a?t/ k .tu6)uo"l#u,ns/n

fOh )

CH, O

'Nd

+ctwllv alcnh0

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.* aPl- o\ido{torr shd1a{d A(trlf * ant aat Pn{" t of \ t*+,a,t 1,.

tf wirtp iFfu Snctionoj

aldrh4dl

u{vt1.

-cH

fo-

* Difficu lt +c oitclxd f,,"il*" dur lc

X br?Ab\
'rt

brzabtw C-C wnd F

C-C

*.

Tel rt qtdt hvdo -Pe cay6l Dol t'o - c lW lsl 4 C u"c* clr,t4 rb prc")uc,t
frrst
,,

disfill

# re .4". reMwe ZH / o i-> H"C^.]l,u 0H /n,,r;Sg,"np

a{c&J)

anoikr

fl fi

ttfl

H{+t

efl,CH

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rA

k- 1-o -

VLtl0

::];fu

nr<imro

ApW totrla ryri

_,
|
I

-ffU

w
CLIrI

{Yrd+1

)_, l^,

dh

hLxan P
C

no* 4 *rwefhy( buxaw

th0 gfialed
u,rb"ryt

hpx
7

chosz-

"{- positru 4

0.+

mrhyl

asfrav(l groap

(atLaru

)+

-^rtQ

#,vt /cng*r*

oarhc, rhai

baf" nunnber qse {< 6e1rlon

qse das r -

fill

rurbm\

'arbtn 3i

l,san.l q allca$

9rL,* +- +dr^

CH-.(t-+

: rH \.

(11 L

i It'i r.

'ai

'r

H CH*
l-t

Es-_

5
A/B

becal;.gt rvurs* $tlot^l -lt{

3 1d*1 -+ -{ql"ttqt cannc* Xs J-*t+f*ll -)-/-lh1l

e

pontaru)

$,s* {han t$

,*

"Jaho'bt*

$llod ae"

,4dY
heotone

4&-mo
Wrfio

-:&
I
\i.

4+ L

c6osc 5w4144 iul,.l;u.n

licNr
cuc-laDrbDartQ

c4,
clobu
a.

H,c
H,

-cFl,
H,

Ibhexane

CH,

-# C oe 5tt *ft
D*t*,"t {.rmqta
_.

gtru&61 TarrVrqla.rna,floorfor

farln*la, 6n?rtt^l

6r'Yttdr, eFde{al

! t qtrrytrt(

-rfrntt

'-f|r,

\ ,/e\

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ffir*,

h^dW

Au{bb b*d 4 Carb6y\ ch6.tu ao , b* _ -

* --*

dwbV. band II be bu* * )- prw

{a c'

dtt=CH,iry=ei
bLff-

r*c
+W ans
CHt

l-ew

b,^n

is b"tt u
*u

CH"-_ cH

b,{f^

t-zra

-a- melhl

I U+- t- q,,a

3 -me-lhy I lnne_r1!
cHt
CHe

4 cH^

:
CH

cHcH

lhex--1*eN
alVono

o"ho x 6e

en!

!-nt

sn4-

ail
3-rnethy

no. ,+ e 2tN6
piatts,l(.

lu,lo

*lruc-tutztl lsolo1g1,,t*

:,.rt (^ as, ho\ro@ .#&

-,.N*

024;* )*L)

)-)

,-:-)-:

.{,i- qcli*a(t cS 6a Vaa). -{B t:"1*t

L+/,,tL-**wp"r. q"*thrc1.

t I ae LLe-+*r,L{t^e-r -tl^Q l,_ ' (ti)2 - rn(,lhvlbu{tanl ?\ rope.l *

(iit)

2,2-ctt

It'nf

15

lsc',Wr4

tl

tJt
hey.ane

N$fc: e e+nln n^o,y4 F6UR

laa,al

et

(rii) ? -*o+\ttywtanr-

-cI

CiD Z.t 2 - dwelhyl b,fia ru

v) a,3 - diw
agA

= nn0tc.i4 r,tf

.rr,,cl.-rJ.0

ttnctrgtr'l
, 4, i "'
J

T*?

-C-CLC_C-

,jri

i-r-riau +hana afu ( a"fu,

ACaptain's Product

rlt

vv -a-f.-

-c -o(
atcotaol

c-cI

ol
1

)-aH

i;; dn.w
-futd-onal

g<, 3ffil

Sl,rwtUAs h-^ti

g^(nL

fl,
crrn

4l

#rl

gl6icttrO

[,t^"-j

stYqctto"rtl

(sdr"c rISQ,w

"=:.^;- hp.ato- saua X' "lrffwt'X

iWyk

c*ro,n"/

n,*lord

ow

4 th! IEowa,r ",E lailocl

--- T -L*C":c)-C-

cis-

bu*

-z14ru

bulen fioit
3

qcid

dcd

olohexane
subW

CrS-

l,)-du

'*ranS

- l,)

-chicdac,4cloWXanl

t-cctl

- c.H

C=L. \7

C- (

CH

:cilCft

Crs- ieoulrg

(r)

to,

'";.",,Y-4
,,r-1tarrc -komer rrruct haue .fr,

nuv! qt&p ?h Ad-, a,t$on

dtdp".

cis

Mo* L=c
L/."

h^tJL *is-'lans, ?dornors b,,,f

-rtanc

Vornera

N4

+ll

', C>H,,

4di
qnt

can ghiw

Cis

* jr*,5

-l

- erw

=Cptrfurw

i -C,-9 -

V\z-Avq

Cis

- +rarq

Mu\ ,80 &o rcd ha,v(

iean^zrt

(r. *c-c--L*rans -DQ/rt

)-enl

-me thy

I b,,t - >- t^t

-C=C--C.-C_
- rn +h.l lb

Co*cfusLo.,,

is (r@,tl,o lqvt A

3 _ meihvlburtrru

fu

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No:"-----.
D*e:

nol

a clrir&l Utfrh
=

H = CI{ cHclcHs nwtbor "l s,lvru isom ers

g'

trl*l e

.r,tt,ia 4 ltontc

@hidl

0i)
itS
isomo,r

\
Eanlt4rsr.

(;r)

*ang,

il\'c-Gl

cM
arQ- N01

l'l,ft] [+,

E*J

{-s'fqasrrrpr

cH, c}l s

tri)

"lrzne

{?!-w
H,(tts

-fixe

glsey

- --

_-_

_ t___
l

@wamu

l0,t
Qpadrcn

%,
allarres

Madtorr*sm

, {r, -

.:::A-: EH 'n'n4

tt^r .Cl Ne aol\f '+a

ovrc0

VYa4E

C-q

WLd

+o.&ff
il,r{altiE,---Cl

\r *zlltl C( W k! toa\dto', Jl I Lffiruufi

9o

raAiCty

ln ututatr*

readtcn iaacP

sf';l/

hse

Uru- Clr @_ 4' +* @te-::'* redcfr*t c'snlt

l6,tg

Um;a

il-ctqilioGrLil

Frze redical s6stlt.droq of

Terharlrsm
fnilr'a*ton

rndharre.

(nrtqne

tr
C\

htmol$t ftsion

n^.

-C\

Y*tlrno#rln'4n*" ta.ht /*rt 'nJ*EJ o"4un*- o'cbc*b ' )""twunry "{ A " ;; /4i t-r// Trtceeotr -r" L C\ tnrfia,tdot -ry't' ->rynr! 'tu'- *;* * { /'?d /to"/ chlorine ltos. *,f*f
a,,
*
H

cf

Pmpqqqlion :

(-c{H r Ig -+ H*1. r l=
I

u tt

,r-"-)vrl\

Ttrminalion ;

Hrl

ct' +.cl + cl-cl

"H4

* 'c{
t/-*\f!
Cl

r,rr\f'kai."l
H
I

{ r+cl

. I
H

-> Go' +'[-Hl ,fr.-frt

CH<

cH*-

+ - cl

dscl

H- 't. + c;
u

-cl -> H-c-Q + -cl t\

H

'i.'1r-., H-c-cl t lcl

I

#c{so -f

cL,

Cq;C:t- 1='-n.'4'{

c,ilrr,

*)

.f

H-c-q
fi
cr-{

+
+

Hcl
rl,c-l

c-ct NA ti H+ c\ I

.-J.ct + 'cl

}cl

-t-,
I

a
H

+ -cl

fH*cl + tnl' + r+C/ cHsct + r.cl -) cH,o\' . ' 'l Cl , =) CH,CJ? -* '{"f CH r Ct *6{-lcl-'+ HCJ Cl|,cl )+ tCl c(l + CL.lcl,, + clr-)CfiCt,r4 +'Ct :? c-Q,' + rl(;t r$1O. -l

* .cl *)

CHs' + ucl

cl,

:)

Cc)s" +

Ct,-*.

cC'U-

+"!(

cl

n-Lci + ort ' 'tti({-'4tY -'

(I

- I-q
q

cl

H--CI

.eF* * r-! -.} Ct *c,{ cl-lr' -; e-l * -*? e"H* e I

G3.
CHSo

*4 *i: *- c.*

[--.t
fl

t ci;ri -) ---rtf----/(Y{

H-J.-.i + "ci
ci
cl
l "C-cl + H tl
i
I

UU"
CI

C'I

*rm,-)
I

cl

ct-C-cl { ,Ll
I
I I

CT

HH Ir H'fI -c- C-H HH

fnednanisrq:

HH
+

M
HBr

Br,

t It -H-i.-J-s. HH

I$hql,\n

Bp4.

UV

.}Br.

-) -t-f ' t
1,

tlEr

't

HH

dhsl

rndical

--}-i.eil,.->
HH

.H

,,-f-1-* + 'Br
HH
bDrno+hqne

Br .\iHr.* -Br
Br.
.+ -

8.,
cHrG{rBr

&Mstr-,0fi. Elhane

'
H

''l:.

f*-H
ll:
'

lrSH :ffi'l
ti1 H
.

i6i"

fq*s nri$ horniqa +o $vL fl'-fl. meckrqni\m Er$rin bq us'inq Br Br \JJ ^

.

rn kV trlh+

llttq.,v

Br,

+ *-i-i-* + rHBr
Br Br

HH

. :..:;;';'r . , :t:;:i.

lw,

trrkqlhn

gffi.
fhcpqqqtiorr

--+

1Br

"

r-i-i{ }1 .a ,flH

'- +l H .--

u.
+

cHs

cl.ltr

HBr

cHscH,-?'-Bl-Br

cHscflrBr

*,Br

h.cH"tsr

+ HBr
8r.

f"-f, t Br 6r
rnin

atisn
Br,_

Bt' t "Br -?
G-Lcl-tr "

t'Br

Glrd-,. B.

AIkAA

prt * &, fi -'ii ,J{c!gr'op\^tf +-t*, du-i f-{!t^} *r.''U

{<woon fl,* Sbutd

^.

tii)

Addilion uri+h H,\drHon Hai'dts

;

?05 mednqn'isrn

*:r;

e^ cH,T cH,

e: {arr**y

\,At^WasiI. ,\t$,ct -t&o z- itoruty

/t
;Br

6+&

@
I

H-. Br
H

;Br

CH-'-Cll,
,- )

r\J
o
:

at( )tvv 1;ntoroV Ot

carbocffinoa^or't t- sauto
-'

--?

QH,-9H,

.rl

HBr

'&i

rntdrqnlsm

t.

CHrcq:ryU
",\
(_-

&B-

cH=

.+ f H-cH cHs
I

cH3gH-{H.H,
'tan)

tri) Addihon u,rtth u,rater U{$drah-o nr

rnerlmnrvr:H.,..

carb0cxLtlon

l\

ict-

CHr

- rr I t

tH-!H

ct-t.

tl

ct

H"Uu*
^'nt\
H

gt &

-CH'+

H-t-trr- + rF,," r:oH- --r

HV

L,

--[-},-n
lr i\6H
elh ano\

f iv)

Adt,l,-on hri+h hqlogerr t !,{qlo$ono{t-0n)

tqhad.,to ro N\ethan e

alktno-

(;\

1a) " r^ri{[

Ht.

tl,

=c(\ .H

t Br,
tn cct*)

r't ,

HH
H

-t-J- u rl
Br
Ff'

Br

BrcB.
H11

[r n L

'

''0"'

H- I

-lul*
I

+ :Br

Br
H

H-t.UBr---)n-t. t-h
br Br

tb)

Addifion

'n,,fli ffi

l*lqnn

cH._:cH, + r Br, (nt)

he ch qrisrn

+ HrO + flr-T, Br Br

CH. -CH.,

Br

oH

l*
hH

+ HBr

sx,fldlAf;
:Br 'lQH,-QH, + i"' ---+ \4 .+

Hro <+

H+ + oH

i,t-,^-'-ffi+-*
Er

Ll+

o{,-bl, t
Br

. Br-

/^L./L.Jf

BrV

ha@

ft")

?*'^4

b. \,
H+ + Bi--+
H

fi alav r

Nff'n?,

s*par rfq(r,

Pg 4E)

h) .. S* ] mrhanism : +D eghin llttstifuiibn rh l" haloyeo"Jl.a.{r lleilcacr [.tr*. H w*+g t' />' ar 3' TD"- \ ^rr, > ti, .-i-H t Br A a ,s')oote'- in''d'e ia etg nfl'{^ cl'[f,oBsf + duO H nudafhllu
0t1

trarru

g- /or^sif,J

----rr'*-u;f"fluYo)

dhotno I b*rnoalhatE rrt*'qqNm : rzoglnpn oc(urs in ,in3\u *at , involut I

BF,-'r:...> I I I "now =Zt-tu* I *' 7i_n. I ffi,"r

r -:^-,*i""'?"*.1-

#;x,",, L
,ng ais-t

&: arta* {h. rrornilOr,u'p- -tD $.* a\ ur,stab[ lntu,u( in; rl,u otqn fofins , *he bond .b*wog tt) A, tk bona bctdeen l$p oty'\ $ carlrcn fi cnrbon qnJ lPrnine d* brcaks
nufuphi[e,
Nrto

X'#Er@

{\,\ l-."
Wy

T I il
tb)

'__

molec,rles
H

iq r-d-s, lslow
Br

'fq)

Hd*,

.1,-n +

o*;J,n t*^ wl

ir#i:i

: I\t \rtelmodia\e 0f hq\ii+rbn state is I+ exists $r gn\v a. sht* "rhtk J

-

not slabl'e

'

Exo'mp[(

tb)

: SN I

*ed1*.i.* . fu extl*,^

Su,bstiluhon

in_8"

haloqensa.\karu

r..'

r . ctl3 CHr.-c*Dr t "t

CH3

OH ---)

t.{w

cH3

m.-i-uu
cHs

6, + Br $' +tug t^auc 2 eZt

I ,.c)pult

intc)ut

methanisrn

rend't'orl occtl.fs

ti) hssion o{ thE

Ct-l_t

c- Br

in l, *"f, , involvo 1 rnoltcult- iq r-d's' 6slow -bond h Srrn a si-ab(q. 3" .^t5ecal-'\n *u![ Y

cHj-f/tst&
cH-r

slro:

CH.-L* t
I

cr{:

Br

%
b,e]ureen

t"!r' V'n1)ffi",v ^U nu-* ulclsr7.a Qvr -A/ 1 lxta.t.t{ * [u r: ,'l Ondlt'ga t'"lll fr*, lo carbo crtr'h ilnict'

tg

enf{

*tsAU

[ii) Rtarhofl

+he

carboca].'1r1

{he CH:
I

oUt-

ion t+ha

nucreophite;

*-fli4)*r 0+]
Ncfu. 3" carbooJiorr

tur

nii\ap,ti-J

Chl" rt

- c- 0H
%
cqn

is iJrr5 stalk - thfftlo{t-

Srry,rd

\o:.
Drtc

J-

[a) & rhs

A4dIrP

gkh7.

@4q \!!dL %'-Fot]q)

rq.*f.e

rll f^ \\"i Xr\4,lI-

-f m
I

r, _ Lhl:Lrl Ll-l =t''"

Ir \-\

.il \llr V

tr

rtl ei* (tl,

\b

C,li

*.;/" fl L-'

-1 '

asL

\) cH-r C CHzCcH:CFl3

Lllt

tl

[\lLi J-brLt?]o- 4 - tac{a;)l a,-{1y2,4'ltr,s{r ;

*-ta.

Subject:......8.Ii.. .. ...........L...........1...........

......

Y.

'.d

L.t"t

=bO^rJ

,fu

Tunku Abdul Rahman Colleee School of Pre-University Studies

Prepared by Choong SH

. . .

Functional group: -C=O (carbonyl group) Aliphatic carbonyt compound: C"H2,O Two types of carbonyl compound:

lntroduction

t&fl

10.5 Ca.rbonvl Compounds 'tVyti& e. irt*t "^tfa.in

Aldehydes Ketones O@
.u.-_^/ro VIIsVI12 U\H
propenal cHr-Q-CHo
(CH"CH,CHO) benzaldehyde

4-melhytbenzatdehyde

Ketone. two alkyl (or aryl) groups attached to the carbonvl carbon atom (no H atom attached to the carbonyl carbon;
R

.o
R'

or RCOR'

1.

Physical Properties of Carbonyl Compounds

Other carbonyl compounds are at room temperature. the highty pgtarised C=O bond, carbonyl ?-T_r9 compounds navb' u -' -'corresponding nargEXoiomp;r;d. Methangl is

(R=alkyl or aryt)

Eg,

2
klun 3.
-

mosfly

pN. iltrdtcl

n0
cH^

r{ 5$c.rn*o C*tnrd'rhatt

hia[i

t ;il;:;th;;

cHrcH?cH2ccHr L.c:o propr@ r"nt,Sn. uHr (cH3cocH;) o lCHrCHrCxlocurl

(not 4-pentanone)

soluble in water

Lowermembers ofcarbonyl compounds are

Hydrogen bonding with water molecules

\r \_/-9-cH. phenylethanone ,C:O b-ut"non. { 4u; qcrE (CH3CH2COCH3) o

cH-

,'":f
-

S*_fl insotub6li*G6

$r

h,,'{an-).-0nI

HigheGar6sq4 compounds are

Due to the preserEe of the large hydrMrbon gr@p

Prieparation of Carbonyt Compoundi 1- Oridati,on of l"'ElffihoK

Gh

reagent acidified potassium dichromate (Vl)

(K2Cr2O/Fl2S04)

1_gg*11* abehyor-$

carborylic acid

cordition: dight warming or distil

,$p',-s
fi'ffi)
+ror

:f:1,"- Esl

r- .",ta(:
ethanal

+Hzo

(a'dlyde)

#;H#-fHs-f\6

or

l'oH

gi

p-

Tunku Abdul Rahffian College Schopf pf Pre-University Studies

[U ,{ e-sJ*d 4-*tV{Pxl"'oI -, X:cHcH o (g z-pr'u116lprt1:6,s1t , /

'1!tJ.

Prepared by Choong SH

I '1,0 ,

lt

a\ le\t
- 7r\
.I

2,

Oxidation of 2" alcohol

reagent acidified KrCrrO, (or acidified KMnOo) condition: reflux product ketone
H

I cH.-!;cx. + tO] -'"n*

cr,o,z'111'

,,O ' cH.-c("n.

Chemical Reaction
*

rro
.1.

propan-2-ol (2" alcohol)

OH

propanone (ketone)

,n acidit*dKtno! l' (OFc-cH.*[OJ*n,. JNCtr y./ \

OH

v\,

t+h

, I-ltrtrvf)

2. Reduction 3. Reaction with HCN 4. Reaction with 2,4-DNpH 5. Fehting's Sotution 6. Tollen's Reagent

Oxidatioi

KIYrno*

/ruso*

, rhntl

?ruryU b Coil--vu6 ,.f,ti m11 Lr,a)

?'rng

. . .

(a) aldehyde . carborytic acid reagent:-addmfrfKa$IUgz (or aciOified KMnOo)

conditirldf' hidaf

.^1. Oxidation , l'l

6trEffiq

(b) ketone:

observation:

arenot oxidised by acidified KrCrrO, (or

'@
. .

acidified KMnOo)

However, ketone can be oxidised with

a more powerful oxidising agent egi oonc. HNO3 refluxing with KMnO4

.n.-"(l
ethanal

+tol

-cr'2o,+-+ "n,

ethanoicacid

"(f,

+tot _9t9lJ*_+@(1.1
: Cr*C a0

"r,-"(fr.

-orq

-{*dffi

",-1*"(lr.co,

ethanoic acid

'.S0{

AT

(.oq,)

"dU!-h

2.
(i) (ii)
(iii)

Reduction
{ttn'tr-rurr'r er.cttu,*t tro'dt1

Reagent (reducing agent): LiAlHoin oryetne.l*h*nu

NaBHo in methanol H, with nickel catatyst

tH ,tto 6n'-cicn, + 2[HI LiArH'in - iry-;i'-' propanone

cH3-c-cH3

ororllr-o,

=trLrI3e

ethanal

aie^#ih* c_rt-c(u * ztnl

IELffi *"r
cH3cH2oH
ethanol

-.Ss$-.

; alcohol

rE--=-lgJ-tF[

atdehyAe

"r,.-*-(l anlffil
.
lo

i:4* "r.

2"arcohol

&1"1on"

:w

-.!9.-* caOoxyfiJ

alc;h

)" akr htrl ICo 5

/: l) auq l|ava.

0 soo +

O*d-t

4ar
d=

,ur6"fuc*L

rcLn

Nz

cHr-C -cH3
,h

Tunku Atrdul Rahnran ColteqeSchool of pre-Urr iversitv Srtiiies

Prepared by Choong SH

Exercise
Draw the structure of the alcohols obtained wtrcn the following carbonyl compounds are
reduced.

3. Reaction with Hydrog"n Cy"niAEEN Reagent HCN withrifaffifnftffiepf NaOH (or

NaCN) as catalyst tryOroxyhitritdl(or cyanohydrin) rype ot reaction: nucleophilic addition

H-<r

(a) methanal (b) benzaldehyde

(c) phenylethanat " Write on paper

froduct:

Q.

-c=N

ot 8*Y

"n-"(on
o

+ HCN

NaOH

,o

2o"c

-'
2

cHl-c -cN
I

OH

/c:0 { f{c
Nac(

q,fioar

.\ as$\ \_i
\.i-*
__{-

\l

to.jorm 2-hydroxy carboxylic acid by ,"nuring with mineralacids (diluted H2SO4)

The hydroxynitrile product is readily hydrolvsed

Mechanism of Nucleophilic Addition

Eg, Reaction of ethanal with HCN

cn^-c( -": " \H

,'o

HCN

NaoH

IoLcpC-_

CH3_C _CN
OH

*-ir*

2Hzo+H+

-renu-),cn-i,{S. *n.
'. Step
2-hydroxypropanoic acid 1: Generation of nucleophile.

6jU-

-)

i.i-t

Na*CN-

Na*

*..C\

nucreonhirerrtl

hVe +o _r1,

t|ln
C

ad ln

6v.

otlo*1

+h.( n

@e'toitr brtap tstY'e{ dte s4

'

}$l&EFS.o.ng.are lrawn towards rre OAtom. the

';W,:c-N-;.;l!:"

Si"HiHE:y"[:f sT,lJl:;"iTL:f#J

Exercise

,o cH.-cicr!, + HcN -#SAc propanone

/,\Y^// ,o *""n,

* HcN

-ff!ht-----

phenylethanone

ltctt
,1/

4'l g=o ICN- ;

CFlr _

=&+

1cN

*pre@a d ba* , * gallibnq*r incraq,u -41/U c6n "f c N- tin ct"b * c- o* (s Iour.i)(rl ) '14!.
ry
,

$4)

i)

O) mo/4

4jq

&r,

t -t t- tt- +H
cN

,-l

"1-l;
tn

CN :AJ

r -,AH ({"t
ctctdr act

yreaa. 4 aclJ , t dQ tr4a6 .ean

frur

,r,r,

( ra.hl ,, ar;"l

sqri 6i) nav( /cf/ , 4 CN : i cvt ,n presut:e' 4oott i ,.n*n*

tl'\') i e 4 raa'ddl {J'{"x

in

*lZa( 4lz nt
(r

c(e4+h

slfn

z
l

ffir.-*

pfitu

Y.[,

Tunku Abdul Rahman Co[lege School of Pre-University Studies

Prep:rr.rl

|y.rd\ (or 2,4-DNPH or

cH, );'.q

_l

l,-l- i @

I N.o,

c.tt r,o,teer'c :

r
x

-i

. . .

reagent.

z,+S$tr{nenyfilrdrazine

(or 2,4-DNPH or Brady's reagent) condition: warm observation: aldehydes + 2,4-DNPH orange ppt.

-lHrD
c,H. | \o, * Hru- ti _@-No, *ut' , ,tc:o
cH.

frt

wam
-

ketone + 2,4-DNPH walrn

orange ppt.

H
DNI Pry

(]P
La
t'p r

.
lt
\

Exercise
yvhat is Fehlirg's solution? lt is an a[<aline solution of omplex copper (ll) ions (a deep blue solution) Use to differentiate aldehyde and ketone Reagent Fehling's solution Conditbn: warm Observation:

/qr
To

. . . .

What do you observe when the compound is warmed and reacted Fehling's solution separately?

Yrl

sY

aldehyde + Fehling's

solution

wam

. fifiltinftfl;$O

V+"I'tl n (b),.c1,< il, J:oJ,

"n.-(on
(c) cH3T-cH3 ho Vln

,',

- Benzaldehyde

rfB*

and ketone:

df{ffip ryfd
no visible reaction

ketone + Fehlang's

solution

wam

[l

.-

6.Tollen's Reagent (A9NO. in NH. solution)

Exercise
What do you'observe when the compound is warmed and reacted reagent separately?

I/Vhat is a Tollen's reagent? lt is a colourless solution

containing complex silve(l) ions, [Ag$tl3)21.

rfr

. Reagent: Tollen's reagent . Condition: warm . Observation:

(")

"r.-4, "VfAt{L
t{,c-l,u;/{
CHs

1n;

sfvor Ntirfir

ketone +

Tolled6-reagent

warm

> no visible reaction

(c) cH3-$-H3

bl'w

(xh

rr\9 utl fXr , f+ dr"ff

y"c?nard, {}<h

ffi;o,,r'5tu*U'i'** )q3 +4l"lHi i }l}fl tn t

:y;,tr-\.,
'+

drv.bt

e[a"ur
1i12{ftarro'\

i l

,.
(

gr,prt

'+o gtoP (s) ,+

al
zs-for< I
,t sle
9
I

o,\

,*r.Xnps'ttinot ah.c Dy.ocht/-+ 4*,r. naic aciJ

Pro Pa n

E i; ;;+"4

ano

huldru*Ll

en1'tr;

Bvtqn_ 2_dna

'CHa
t:l

r l$bPr \
f

bqfan -)-o I

*L'cHc

9.
+otlo,lr):n4 fxn
LA) Lb)

mula (s)

*, $t &q^nic pfwluds (s)frr

./te

'

-J-or,e { hrtand ) Nq cx /

NaCN/XqaH

ca)

ttac{

. bttawe

d bq

i,oarmln

g Nlh /+ ct
fP4C{

& H,. ?+
rfl

tr,iS' Q-c

4ns | @)
el-op

'T

HcN Nrlh MoH (a4 ) c4d r0 -)o'c

/

ra^q0'4: diluta firSO+c^? crrdittoyr: wot vodgr yn+lux

n'drife
larrtn

j*a

nlcohul

I-0arno\f,

i Kmq 0a
ds+ll

t-lrS0+ ra+)
sotrr{Hiun,

.ooJition

,.,ih tl6oQ k1,) lo -Jo" c ( ,rl"l )

0t1

+@rmre

Subirt

/es<,\ 6 ct^'\A\

n_o:.

Date

i
1;

b,+ron

-\-aou

brla,q*t-o(
J " a(coht I

Qktono )

fflHa ?n c{h{ r vtrt urndf vs+lqx

alrnlnr)

E[LO" /H'SCIn Gq,') hLo* ttnder roffu k c alour 9c! uti q

k-&, q /{"sCI+ Coo) Asd ander Wu,q

KetortQ

re

okCo lo q

,i*

cllour glln

-fan-J-ane
CHs
CHn

eH*

+ Hcru. >

CHs

+ H, - c'( { ( atda 4 t radqclicn.

ID.L
- crb

rrarP l&el H * s-tJ , 5.h6il -&a {aue I thtta: 1144 2ra\ ^arb
t.ef

6d
fsz

d
-)r

+e

./ b

x
tL

.J

(Ja I
\./ U
I

,.

=o
=c.
L

5=
CD

o3

x$g

g8
tte

qE
a o

rq

st

ut
/?\

*x
gEz
s
d-8+ o: srL g3q. s q8

( =-l

'd c.v n)(^

l-v

.)

E a

-.1-l16
;E L)

\\.2 t)

.s) rr <5.-, 5

.3i5 C3

CU

c]o

J L)

5
+

C,-

-aJ

TI
s = *
ilrq*gflqer

,f
%6#haoi-x

3A I -r5
(3

t?5 L--

EP

g
J.

ll t_ o -.(J-J
o</

Z q)
t'

r- oJ .1 cj-rry

o$ ?
c---

\y

,N

rf\

$*5^6."**
+7'

o+
\/ \)
I

=J t

dis${

T 'L)

crl

o{idatrlm

B-4
+ur6ta,

? s [o)
*U

.L F\ A-

I hr*,

O s)+c( .= {5r L.

u6 ,o

4,ror-.L (J
..r,/*
.s s-E \-i \ i, >-'
\--ts.i
s(

-$/s.-

$
.S
b

t t

(\
\

.q i e

5d 6G

i{ ]-\c
S\)

\\.sQ' s

\-

d;
E

.D

> : \
tl

>--

S-.s,
S J

:IG

Q-s: r) l<)-rt
6

.x. ov

C)

_s
uo

\FI b sE- / e4\a I tt I *\g

IJ

]s

&

\y=

E
i

v 59 + Fn -Y' n$ s +s/ J+1 $'l* Vt s> (Ja us X :-\ $x x iS

{-\ -:ri( \J
\)
(!,

.< -6.

.\\Q

{r

itr *"t' o q {.FS

ott
^l

t gT+

0*r

O-

ct

-(

$*Ter

+ Jr \J

o5 \./
o
I
rC)

e ,Fd
+,

"6d 3-6 r-s

-= ..> 15 1ni

= J

IE -ls^z of s I+

A lu ti
I

;
o r\,
<,

d)

s)
q') ,

tn
<=

t: L

E3
irC

J. C)<-

z.
:#

\l

a-

rd

\) rr^ Tta: o-{)- \)

I

oo { \/
f\)
rn

d/ +,) -n-

o'
L
ta

--!

El$u.

SP SE
S> dtA
>

e\hr

tj -E
-a al t-

-1"

dl 5 i!/ c. 6- s L-. d El 4. 5 5rG-- o

z r{l (J ,T5-C-e
,

ar:

\J

-L

T.
U
I

rf}

fMr,0qlt[q\ or t_ F y:nf.rfrrrr"r} O=U 3 -u-r- z K.&"orlH.su* .O T orr fq*lux T

I
I

)L)

.4

J z
for{ia,
-,

.11

(,)

oxidation

-1! npbtg

o'l-

^A /1
/

Ln

=-Zi Z
il

&r a,
(.-)

dr'-#

r) fo) I

rF ==E:fl-c X =

.S *le $ei --o. Stl=- =ti <s F ftl ;g*\ TFo,';i=

-,S 3i=

o *,

a J
o

e*s*{i+i!\

Tunku Abdul Rahman College School of pre-University Studies

Pr-epared by

Choong SH

10.6 Carboxylic Acids and Derivativerr"rfrLryl

Carboxylic Acids

Carboxylic Acids

AcylChlorides (A2)
Esters

. Benzoic acid: food preservatives . Ethanoic acid: vinegar . Long chain carboxylic acids: soaps . Hexane-1,6-dioic acid: monomer for nylon 6,6 . Methanoic acid: to coagulate latex

Some Uses of Carboxylic Acidi

lntroduction Functionalgroup: _c(o gatboxvl qroup

toH

Carbonyl group
.ztO

R-c( 'OH .

R = hydrogen, alkyl or aryl

Monocarboxylic acids:

%H.nO, At1y*t

Monocarboxylic

a-c'! toH
cttr-c (
'oH

,9

rnethanoic acid (formic

Otc

6c

.
acil)

Dicarborylic acids;

zfic(ncjic

i B o...
or)t

/sr >r ,"17".@-o

etnarealoic acit (oxalic acict)

(Practical exam:

Hrcro..2Hro)

"r."rrr-"(o "(:"

Prbput"tc ACKJ

;c-cHr-CHr_c( .OH HO

butane-l,4dioicacid

)"-"r,
benzoic acid

-"n,-cH2-cH2-c

,9 rnr.,lld-rru (:, nr t*

G*-"(;

\*@-"(" uo'

benzene-r,4{icarboxyricacid

'oH

^*

Sth

ctt4r

ty"t+'7hi/rc

'fftrf { A 2"7 f

d f*T

-WC a^Adt^* :lhr, L7. PrcparerJ byC..io91g.Sf . hf ,_P, xl)ubttftX, uly'U 0{+q cf)ovr,r r f\ftca,t sfa*c

/T

Exercise

g. ia(oalk >. ,..tF"ho I

+.atdthYott, (

the following acids:

fudnxgfnryoic ad&
H=EniHJoon
3-

1. Either liquids or solids under room conditions 2 M.p,and b.p. are higher than alcohols of similar
molecular mass. Compound Ethanoic acid, CH.COOH propanol, CH3CH2CH2OH Propanoic acirl, CH.CHTCOOH
M, B.p.
118

Physical Prop5rties

/'C

iZfoqa

60 60
74 74

puiug;a

qc; o(

97
141
117

(cy

cr@oo H, -{n cJlbro 2lbqci c

butanol, CH3CH2CH2CH2OH

Why the boiling point of carborylic acids are h(lher?

Each molecule of carboxylic acid can form more intermolecular hydrogen bonding Furthermore,- the intermolecular hydrogen bonds are stronger due to the more polar O-H bonds

Q: At a temperature just above the boiling point, gaseous ethanoic acid has an apparent M, of 2A instead of 60. Why?

\ _e-R .-H-O' R-C..tto' .O_H

___

O.r

ca) becr(rrj.r it i5 $ru,nE a oltwor (hylnge,o k ^d ?ro@"l* ) anr\ tntte.-fittt, +v* rn r ts dtu'blL
cHs CooH

H- o-'

"c-R
fnd)g.uU

dimerisation tr,rqr\r"S

+r0

*.R

hava

3.

-+hob'rc

'@
Oe
Ph"bic,1

6.$ miscible (soluble) with water at room

acit and butanoic acid are completely

conditions

Methanoic acid, ethanoic aciO, propanoic

Preparation of Carboxylic Acids

1.

Oxidation of 1" alcohol

.

&cnH si,itrc zffi

l^

Reagent: acidified KrCrrO, (or acidified KMnOo) Condition: heat or reflux

cH3cH2oH*21o1

ethanol
@-cH.oH
+

ff5
-H-.-.-

ethanoic acid

t
l-

2tol

o$wp
1hlt{C

phenylmethanol

benzoic acid

@
cru$F""",.H)

Turrku Abdul Rahman College School of Pre-University Studies

Prepared by Choong SH

1"

at;hot

_!E- auehyoe--Pl- Iiloryric acio

2. Oxidation of atdehyde - Reagent: acidified KrCrrO, - Condition: heat or reflux

(or acidified KMnOo)

w(

-RCOOH

r(f, "r,-

. tol

-#g.ll- . .n,-"(fn
ethanoic acid
acidi"edrqcr,oT

ethanal @-a(o +[o] - 'H

heat

e-.lo tOH

benzaldehyde

benzoic acid

3.

Hydrolysis of nitrile
Reagent dilute HrSOo (or dilute HCI)

ll

Carboxylic acids can also be obtained by refluxing nitriles with aqueous NaOH (alialine solution) followed by acidification to liberate the acid from its salt

CH3CN + H2O +

OH-

renux

CH3COO- + NH3
I

lH.
CH3CN + 2HzO + 11+

--I9!u

..-* CH3COOH + NH4.

cH3cooH

Exercise
Write the product when the fo[owing nitrile compounds are heated separately with dilute
acid.
t

. cH3-cH2-cN '1

CHs-

cFl

4'U

, t"a:-cN)cfl, - f{-':h cHg

o{,*
'

Chemical Reactions of Carboxylic Acids

1.

Formation of salts 2.1 Hydrolysis of esters

2. Formation of esters

Tunku Abdul Rahman College School ol Pre-Universitv Studies

Prepared by Choong SH

1.
-

Formation of Salts

Carboxylic acid reacts with bases, carbonates, hydrogen carbonates and metals to form salts
With bases. form salts and water

-With carbonates and hydrogen carbonates:

form salts, water and liberate COz(g)
3COOH + CaCOs

(CH3COO)2Ca + COz + HzO

wYita ac.dtirct

CH3CH2COOH+ NaHCO3

joort2r'raoH

9uoH

IgH*cH3CH2cooK+H2o

CH.CHzCOONa + COz + Hzo

- l*."r.
*

COO'Na*

2Hze or

2CH3COOH +

PbCO:-

(CH3COO)2Pb + COz + HzO

-With metal: form salts dnd liberate Hr(g)

Joo"+ar.rro11
Na2CzOa +2HzO
(CH3COO)2Mg + H2O

2CH3COOH + Mg - (CHTCOO)rMg + H, 2HCOOH + Zn (HCOO)ln

2CH.COOH + MgO

-rr-S

IEG,

c-L fi tat I c=o do4 <c*4

4 Bf

bera.$?
hr(t Heo.,

ff

. .

2.

Formation of Esters (Esterification)

CH3CH2COOH

Reagent: alcohol Condition: reflux with a litUe concenkated HrSOo as

act as catalyst

* HOCH.CH,Sn"

ffi',so'd{r -cfft'CI oclb4

+H,
ethyl propanoate

eqlm snift

.-

propanoic

acid ethanol
HH

'Ih'o rPdqcl nc9d1&

ei-f{

MY

carboxylic

: R'oH _;fr_qlacid alcohol--- reau .ethanol

*"**,*
ester

r,p

C-ff*

-''"-""+;-&-cH'

{"ro^J .*.-"{fr \_g .

ethanoic

cu.cr,o@se!=*o;r.-"(l^..
^.
ethyl sh3noa;ie

acid

'OCH2CH3 -

",o

G>-L-o-f -i-'H' -cHj + 4 c*4lt

=se

t-ra

Confirmatory Test for Carboxylic Acids

Add Na.CO, to the carboxylic acids -COrevolved (+vereaction) OX pq4*ol

caq+

fucqtse

oH +

ako a-tifltta H

Carboxylic Acids and its Derivatives

1.
Esters

2.
3.

Acy[acid chlorides (A2)

Amides (A2)

,rrq^*,\ ao{':l'*kue sr tn ) aULW 4b**t ), k-*NPLI

a(rc), J') -

rxtuzlltt

a-ciJ

)-\/at (dt
p cts

-2

Tunku Abdul Rahman Coltege School of pre-University Studies

Prepared by Choong SH

Some Uses of Esters 1. Artificial flavouring for food: fruity smell

physical properties
1Fruity smell
Methyl butanoate, CH3CH2CH2COOGH3: appte Pentyl ethanoate, CH3COOCH2CH2CFI3CH2CH3: banana

2. As perfumes 3. As solvents for paints and varnishes 4. To make polymer (eg, polyester)

Ethylmethanoate: raspbeny essence lmethylbutyl ethanoate: pear essence

2. 3. 4. .

Ethytbutanoate, CH3CH2CH2COOCTHT,ptneappte Ethyl methanoate, HCOOCTH.: rum

lnsoluble in water except methyl methanoate, HCOOCH3 Lower boiling point than carboxylic acids Cannot form hydrogen bonding

Neutral

NOTE!!

Exercise
Compound Memyl metnanoate Relative molecular mass Boiling

pointfc

. -

60 60

the same number of carbon atoms

acid): molecular formula: CrHoO,

Esters are isomeric with carboxylic acids with

HCOOCH3 (ester) and CH3COOH (carboxylic

Ethanoic

eid

32

Exptain rhedifierence in aoimg

pot,tiEGG#ffioi

t18

Is{:
olww z^ d'"

,/

y.

l:.ll-.1^1"-1.ic

aci<r is higher 6ecause motecutes of ethanoic

formula: C4HBO2

CH3COOCH2CH3 (ester) and CH3CH2CH,COOH (carboxylic acid): molecular

hy&ogen bonds berause there are no
bonded to

Jta,.i
oxygenhyaag* H_q _OCH3

f* AJ-

a"r, th"t'"r;
methyt

o
orce-sbe-h,veenrnolecuesof methanoaG are the weak van der Wads.

l1

*fj:11,"]1,:p]ytarf

Fcrerfication

Preparation of Ester

Reagent alcohol

lNrS.ascafidyst

9!rfm:

reflux with a titfle concentrated

GilI|tail+dcotrc{ *

Chemical Reaction of Ester

ester+ water

Tunku Abdul Rahman College School of Pre-University Studies

Prepared by Choong SH

(a) Acid hvdrolysis . Condition: heat or reflux wilh dilute .

1.

Hydrolysis
HrSOn (or

(b) Alkaline hvdrolvsis (saoonilication-makinq soao)

. . .

Condition:rcffi.
Product sodiumsaltofthecarboxylicacidandalcohol(or
potassium salt of the carboxylic acid and alcohol) The sodium salt formed is then added with acid (eg HCI (aq)) to liberate the carboxylic acid

dilute HCI) Products: carUolytic acid and alcohol it is a reversible reaction)

"*'"(l
ethyt

Ca&c1t'c

"","r.#/'qlsethanoate soo,u.nfunoate
-{-*

""{#"n.*dl
euranor

-Lr,o
ethyl ethanoate

#<.cH3cH2oH
ethanoic

acid

ethanol

ftry 61n"\a

A2 Syllabus . Formation of acyl chlorides . Acidity of carboxylic acids . Hydrolysis of acyl chlorides . Reaction of acylchlorides . Relative ease of hydrolysis of acyl chlorides,

. .

alkylchlorides and aryl chlorides

Formation of esters from acyl chlorides Formation of polyesters

-l-

rt .J'i
\)

2 ra
Alo
>

n,9
-1

s \-))\)

3.*.
\J

+o

a'.1

i.rJ

"-b
'1

r,
O ./\' <i'
'

.'i - -r

.;

?uit rO 9+ *5. -> UNt

l. Lto rtt
c'l

I t-

e-83+j uas,
- \--l

2.15\

.s-)

r>

-f+1 'U \,
^lV

*\)

\-)

l:t

L)

z.

\) /l d _9 \J

\r I
dt 6 *z\y
\

o\% ?

s\a n ,\ s E OtL'1. G

f,^tr\r,. . f:o7a[\rrr...
.

AdJyor '
oT d/
r

irt*'

^. rlua 4"+)r
..

o.o :r
\./ ()
I

ffi
_r-

T (J.l
'l|

T o ri

T,(
t)
14

rf)

-f rO:

oxiilahton

$j{-"
d'
s?

*ur# .\3 \ /.\i

. ().o\J.

"-g
I
f1l-r

q) -

r#
&u

o
+

-c.

*(o .Zy.\
{'

\\ ,/ U

5=')
:l

L)\

LJ\
tft

J_

E;
.) (-,

_o

-d

L) rfl

O d

T (-)

:r LJ

?1

-L,

t
o* \ .2"
-l(\

U 6r}

l'unku Abdtrl Rahrnan College Schotrl of Pre-Liniversitv Studies

Prepared by Choong SH

. f6tr84{ir
.

6r

lntroduction

10.8 Polymerisation
Addition polymerisation Condensation polymerisation (A2)

a large molecule made by linking iigHho r"ny sriatter ones, called The process or chemical reaction in which of joining many smaller molecules of the monomer react together to form the largg molecules of polyrnerio oelled Types of polymerisation.

ionoie

Addition polymerisation Condensation polymerisation (A2)

Characteristics

The monomers contain carbon-carbon double bonds

. Addition Polymerisation
It is a process of joining many monomers together to form a large

One type of func{ionat group

The empirical formula of the polymer is the same as the monomer

@lA-rs
molecule without any small molecule like water, HCI being eliminated-

rD Durinq polymerisation, there i5 the monomers are simply 'added'together to form the polymer (in other words, by-products are not forrned)

9@

- The M, of the polymer

is an exact muttiple of the

M.of the monomer

Monomer: unsaturated Polymer: saturated YIO

bon a\

Polymer: poly(ethene) Monomer. ethene One repeating unit:

-c-cII HH
^ ^oooi9

HH ll

f+,. /tl f1'il n c=c Srcc \H '

q'

tri ,i

N'r'"
HDPE

S^

bottles, cups, buckets

Trrnku Abdul Rahnran College School of pre-University Srudies

Production of plasti"
Agiant bubble of a
tough, transparent plastic film emerges from the die of an extruding machine. The film is used in packaging, consumer products, and food_ service operations

p-OrG

h'

C=C

/t

LJ

-c(

W iril @w ':"#e,1:
W V 'fu-.,.
:.4,.
i

Polymer: poly(chtoroethene) Monomer: chloroethene One repeating unit: lf

l':= gramophone records

sisffiuiia,slisii
=tr.i;t'atBriffe.

@U!Ig.rr*Cs.

rr:

poly(phenylethene) or polystyrene styrene

Exercise
Write the equation for the polymerisation of propene. (a)Give the name of the potymer

Repeating

unit: H H lt

@) h @O{=cfr,+

.A

polgpvoqa

LI

(blDraw one repeat unit

(c)Draw two repeat unit (d)What type of polymerisation does the polymer undergo?

f + +1" HG>

rn
Exercise
Give the equation for the polymerisation of

4i*,t,
eofylaifils
, ,.

Probtems of Disposat of

o
CH.-C-CH=CC|CH3
rl

Addition polymers haye no.reao*ive.eite

- They are noa&bd6gr84#$.,* - Remain without decomposing for a very long time - Leads to a shortage of land for landntt

):-1,,,*#t5-l
flnctrottr.t 1au

ourn wtth the formation of torlB@SS Obf pvq HCN from poty(propenenitrile) Possible solution or altematives:

"itu" -Plastic.wastes may be bumed but some plastacs

fro,

Develop and use biodegradable plastics or photodegradable plastics Recycle and re-use plastr-cs

Tunktr Abdul Rahman College School of pre-Universitv Studies

Prepared by Choong SH

A2 Sy[abus
Condensation polymerisation
-l

"

ai"' il Lenz ildl !Q,- f'^ .-_*I--*::****'-_-_\-*

qL

cLt-l.,A

ck

>iA,lFE) .
=

fhe'ryl

s1h6'u*L

" <>lfudt
2atba
vu1+^

J)HllLlhatant
,
tI^

bwor 'A offi, b.f a ?f . b"nn' +*'a4 'r'fco n,bor,l' c'l Cli;.q a* .-l' rty I { a\6
o 7r ,^,t 74 tafa '\)li/\ u ovvv'- 5 a e[LtaU. ;n. *f*:'*f ,-, nragnitl"k + ovt CA$llryt \e 2<rru'tt, ,,:, Iv1afwl4# T {+ (/'t catryt l darr, , "/,d -+l^rgz( "( ArzUcce'tbon 3*-/) ^t'|<LuA {yn 4 bartcl ' ;l+1, &

<>g&>'JWvwl+lM foa'> a *oijr. a'l

t I -f'l

'

A<ir <)^)lv -lt'\etr O^N ^'/bc"'t'?

Sl*O O"llOCrle

;;;rflf

) #*,r/-

,,:,:*;":;'# Ja1"rt' 10 1v
4!.r\L.tr
o

*cr?*,1qr. !+ 0r1 ,^tbvyl c 'k*uy,+ht. {+ u, caq'v' L

e'a,nlrn?.*r)
cieaTtre
'

',O
,

t1L,r prt5znq,/ hgoLncavt*nry*f *7* 1 ;" h,nd-(.r, +ta ^7y ati,t .a-Wol Cdai; Arnc/mn &

CZ.baaw,voy) . SN, tn:!fu?' u '

iHxjiu cHriclll ftlglcH *.i:L'i.

;?i

r-Prru nltbutantttial

grU,
-, u.

^ tr^,.t 1 ro<L' nru*hyl1 tuz ) < g,. r <) " < l'<*^r{l/,

-.t- , rn-ttt

..0

l,t Wryl ,ro-at4t+tl {..r*r1.tr(' . .., ,o^i,ou,'r). -l.ov:o,r.lr* n)1)):e"pt'fic aato?fin

cbtrocytrt,Z cr&r,o

u-i-rr
:'j.

r*Jnl

q- l--B

?. i"@rL-rt

'

ie*(tufrJ I

,pr*

usS paxl!

b@,-L:-e

u' cr"npa,e +W aaar'lin nrclt te d! .( Q'ftiu

be>g-6)e*
0)d rXn +,AA

Q.rx
3"
roarhue

reacttq {,

2B,cux@r )o
/" /'

/e"t{

,raoxf-

Nlagl a

re

4r : {p 4^bf
wj*d

c'

(><tt

c*tx <kcfl,A <4w JO

tu\dhyl

ro

vy11fl16il9n

aot,n

N,tdaopnrtr c

*t :;rY .f,t.'ffu,o"" Wty "# -r,ffkr*

aad.tfi"a

=1#b s tlox u- ,ftrn

<P'cx 3: Fo* ,,'!''

c

'ri nri'o'u

,t 4Atry,*

*',J

4 A chaia

*?

Clw o|'{'tg tct4f al"

+Lc

T ; i:o' +i ^lc{/ /'a-/ic(t t'xr*4+r:{e

a,rlcn,,.'u
)i*ffiu

"

o cH.,-- cHcH'gocHs

'@ 4- Pe,nu-

b.
Tunku Abdul Rahman College School of Pre-University Studies

crmn

oid

4o*, a4natfuy dmsiar

w url*,Sk7

Prepared by Choong SH

Chapter 9.1 The Periodic Tabte: Chemical Periodicity

The Modern periodic Table

lncreasing atornic (protoh) number, Z Horizontal row: period e, Vertical colurnn: group
s*
Bt

\
,LIIE
2 t.i i\ru![r.

frr.arur,,r t[urt:,*,,

{l --- ---- --I CI ilo rt,Cl ll:tliz. "nt K ai S. li:v r;, :).E a ltl' $ )' 7-r i Xh ltr 't'( r{ : f,fi pa-::q ; q.i , ,,

, ai

(ii $. Ini:ltr :tfe-i.ir & ik; tr lt :,\r

Br:lc:.re
'l.ru.Jrr.l.
rqBiJr
\19

::hE:
+-

t :t ::l.l,.,ti

: [r

,Is: (:t ll'

*c & :Ilr M lr t,, \d l\{ iB t \! t\

j. i r] : r{ {il

Variation ( or Periodicity) in the Physical Properties with Proton Numbers for the 3rd Feriod Elements
:

.,i.(\

ft ,*

tr\ IIn Lr l0 : Ut lr
(

vr$

{h tr

}.. tin }td \,

l.r

.,rI i:,il!{i

1. Atomic radius 2. lonic radius 3. lnlE 4. Electronegativity 5. Melting point, boiting point 6. Eleclricalconduclivity

;.1

ffiul f,-:
{----J

Prepared by Choong SH

l+is4.',$il

Tunku Abdul Rahman College School of Pre-Universify Studies

"\-@z''
Factors determining size of atom

t.
-

Nuclearcharge

{ qrofiD' no)

ln short

Depends ofnumber of Protons lf the number of protons T, the nuclear chargel' and the nucleus will attract the electron more strongly. Therefore the atomic size/ radius l.

;[f Srph3'6r,t&rdomic

radius

z. Screening effect (or shielding ettecg (inrtt r

mis
is ttre repulsion effeci between the electrons in the completed inner shells and the outer valence electrons lfthe number ofinner shells 1, the screening effect 1, the attraction of the positive nucleus for the negative electrons I therefore the atomic size/ radius

-lf sct '\h CL\tf

ic radius {

:
p:

S'za

r"t.*

1.
Graph

Atomic Radius

(a) Acroes a period, atomic:radius

because nuclear charqe t. but screening effect stav almost the same (reason: nuclear charge 1 because number of
Drotons

screening effect stay almost the same because number of eleclron Shells stays the same)6t9 #{ qf'fi4 So, atomic radius

tnars

I'e*4 - s'Qi 4

n.t nuc\oar 6ic^r!e t #adr'n

A*rn'^

(b)

Down the group, atomic radii

eg, Li

Na
t

Z=3 Z=11

I
2:1

2.
r; Graph 2.8.1

lonic Radius

because proton number t - Screening effect T, because more inner shells -However, screeninq effect outweigh the increase in the nuclear charge. -Hence. net nuclear charge decreases

-Nudear charge

So atomic radius

-, kt,lnic racJi.rs and

ro n;c

Y^diuS

4ft ) a,u.t! 6yt

deo{l.p'st.*

cr(W{

ftl

4
( iso e)ectotl'ic

,nud aar

*+
*,'"*'-;+'^J

dS t, (

*tt l

4,

nqde{
t=qofi tr"S

(il,ttr-r"aaD

iso'etochiini

lsoelecl,roatc

t(a
.8.

J.8.

J.e.3

frtn-^

pfiool

nttc\LtuY c,W

(stu 4 alav: "

t,

AoY

a-lrnoct

sg7tyl^.L

n*vu-bpr

4 6nntr 3f
)f

dactvon

t-

')-

l+
Nla

fr

ffi.@ilffir

No:..
Sub,iect:

Date:

%ehO

lErw
Edl^tn

tht

@amr*nrgr

www.cosrarionerv. com

Prepared by Choong SH

Tunku Abdul Rahman College School of Pre-University Studies

c A cation (eg Na.) igsmaller than its atom (eg

from Na*, Mgz+,

i

414+

to Si4*

ilHffiflI&,.
E

are isoel ectro n c (tffi"fit$..smn e ), btr{he*iitf8iBe'f*estffg.s'

Na) because a cation has one electron shell less'than an atom (eg Na*:2.8 (2 shells) but Na: 2.8.1 (3 shells)). An anion (eg, Cll is bioqer than the atom (eg, Cl) because the anion has more electron'(eg, Cl-: 2.8.8 (18e)) than the atom (eg Cl: 2.8.7 (17e)). Since the nuclear charge is the same (Cl- and Cl have 17p) the electron in the Cl- are less strongly attracted by the nucleus. 17p 17e CI CT 17p 18e

The i&id,&tffit&F#om P&, s2- to cl they are isoel ectron ic (ha4t:*r$p*m*mumrer ), blertu.-

.bffir

ln short: =

lonic radius of +ve ions are smaller than their coresponding atomic radius.

affi""= {61.z1Clt

foniL racliuS t radiqs--, htonic !w'e)'

3.

First lonisation Enerqy, IE

q@* W

- lonic radius of *ve ions are greater than

their corresponding atomic radius.

X(g)-X.(g)+e
X* (g)
X2* (g)

AH=1srlE.
aH

Same number of electrons (isoelectronic series), ionic radius as the atomic

- X'* (g) * " - X3'(g) + e

2nd lE
15

AH = lro

number I

(a) Across a period, first lE generally

Graph

Atomic radius J, nuclear charge f , screening effect stay almost the same = electrons are more tightly bound to nucleus energy need to remove the electron J

+lEf
lE of Mg > first lE of Al
1s2 2s2 2'p6 3s2 1s2 2s2 2p63s2
1

- First
Mgr

ti reasoni

Al:

3pl

e Al has a lower

remove a 3p electron in Al than 3s electron in Mg since the 3p electron is further away from the nucleus and less strongly attracted by it.

"t lE because less energy is requi red to

Prepared by Choong SH

Tunku Abdul Rahman College School of Pre-University Studies

--

First lE of P > first lE of S

reason:

ffiffi
r.

P: 1s2 2s2 2p6 3s2

3p3

S: 1s2 2s2 2p6 3s2 3pa

S has a lower 1 st IE because less energy is required to remove an electr$ trom pdred 3p eMorrs in S since fie decfan e<perisrce hner-pair repulsion

$**',{ffi W*wtt*# wrM ffilr'e',;:t.*.'

'\-

'
1.

4.'ElectronegativitY

1' -

tttrAgbr charge fbecause proton number 1 g-$eqt 1 because number of electron Brt

^,ffi'

""t shelts

However, screening effect ouiweigh the increase in the nuclear.charge Hence, net nuclear charge J Less energy is the atom First lE J

I "nip

Definition: A measure of the ability of the atom to attract the electrons in a covalent bond. (eleclron pulling'Power) Follow the same trend as lE.

neded to remove the electron from

2.

rbt
ei-ve

t | ffi Iffi

11 Iffi

ffi@*

lE1 E/-ve

rhird

Na-

Period
-Al

5. Melting Point, Boiling Point

3rd Period

n'%T'
- P,, S.

Ct

simple

Mg ffi - m.p l from Na to lm - Na,.Mg, Al: metallic bond (metall&

rnoleqrles,
- weak

covalent force

,s
l$l

rrdPfliod

Al

lH""lIi'", *"Mtg),P"{=
sbongpr metiallic

s,boruerthe mblallic bond ffi - eg, m.p of Mg>Na because Mg g has doiate 2e, Na donatele, MS

*"

VDw between molecrles l{0 - snall quantily energy is required to breakihe weak tm

lil

rm

(d)

P, S, Cl, Ar (P1, SB, Cl2, Ar) - m.p l.generally (due to

bond

m0

ffi

a!-Sii
- tlrp-

t stlarpU fom

Al to

Si

m
0

s _ weak m il VDW a0 - mp. S > P, because lhe 58 1-----rq-'{ molecules has more electrons I l-----r-)r+ H,T#"1"ki#l#:'arestron*er rr !2 t c t

SEiil*1ffi:i$:tr"fEft, is .Eded to break the

-a

unn$n

r?

t8

sfrolg coftfeil borids between Si

H dcrsgr .tflns

m-o- verv low m.p, very weak intermolearlar forces - Ar (monoatomic gas), mass of fu ia relatively lower than Cl2 gas

l.-iu-*",rr.ldirloTg
mo6arle) molEcule),

:*gffi

ho)n

T;'-{'f^-*

Prepared by Choong SH

Tunku Abdul Rahrnan College School of Pre-University Sh-rdies

6.
e Graph

Electrical ConductivitY

e,

Na, Mg, Al: are metal

-.Can conduct electricity :- Good electrical conductor - Al is the best conductor because Al

s Si: semi conductor

- Used in silicon chip

'

for computers,

calculators.

e P, S, Cl: nonconductor

'

./-delocalises-3 -ffil6iE-ifrio

?6tffihEsZ

the elestron cloud when it forms the metallic bond. Mg oT1fr

Because theY have no delocalised

Ectl6-n]frifi?ir-*
crystal structures (Po, s8, cl2)

(41 neactiohs of the elements (Na to S) with oxygen, chlorine and water
x,

Refer to the extra handouts

Chemical Reactions of the Elements in the 3rd Period

(B) Variation in Oxidation Number of

the Oxides and Chlorides

(C) Reactions of Oxides of Period 3 Elements with Water

E Refer to the extra handouts

Refer td the extra

andouts

"*r"f'

Ftsi*t

in"araSa.nlC 6ktrt'Prepared by Choong SH

(i) Reaction of oxides with water: (acid/base character of oxides)

NazO

e Al2O3(amphoteric) and SiO, (neutral or acidic a bit)

react vigorously in water

-do
c;

not dissolve in water

NarO (s) + HzO (l) sodium

oxide (basic)

2NaOH (aq) sodium hydroxide strong alkaline (pH = 13).

PaOro and SO,/SO.

MgO

SliqhUy soluble in water

(basic)

MgO (s) + HzO

(t)

fi/tg

(oH),

fiql

weak alkali (pH=9)

(aq) a aEidic sup"ffius acid SOg(g) + HzO 0 * H2SO4 (aq)

SOz (g) + HzO (t)

BlFtr. 6H2o(r) * aoclic-

4H.Poo(aq)
phosphoric (Vlacid

HrSO"

il6?liE

sutprfi?ii acid

-__ of lro,r, w*i,.4lanlf +

r Across Period
so2/so3).

fi

nrda"r 0xre\1 + Il-0 ->r,wt{a) l+ldnndl

A-D

ac'$
acidi Amphoteric oxide Reacts with both acid and alkali AlrO, (s) +0 HCt (aq)O2AlCt. (aq) + 3 HzO (t)

(ii) Reaction of oxides with NaOH and/or

3, the nature of the oxides

changes from basic (NarO, MgO) through amphoteric (Al2O3) to acidic (SiOr, poO.,o and
e NazO and MgO

A[O.(s] +2 NaOHtaql

ffih@irgq
SiO, (s)

EdH

+$Fffi

NaAt(OH)o (aq)

t,.,

Basic oxides

-Acidicoxides
2 NaOH (aq) N P.O,o 12 NaoH (aq) 19))t

lsodium aluminate 2 k*tta41f

r'^

Nar

:I

* 2NaCt(aq) + HzO o MSO (,S) (aq) 1(HCI - MsCt2 (aq) + H2O (t) , (9tlrd ) ff l:r,q'c g,d!. t dt',d) sali + Yl.rC
Naro (s) + zHCt (aq)

so,

-so

(g) + 2 NaoH (aq) (aq)

onosphate

.k

So. (s) + 2 NaoH

-{.

;'Am'rPhg+P{'i6

lflnrytnrtJ.ti

3te6\1d)

pf;.,f !a+@ft a.c''d ? s</{ + Fl" 0 + aho-liv,,g--r H,0 -) *al't (rr\J \1_c'0?+ caA+ Gg6.at1l"l[
.)( 6c,s\'c oxdt + alFqliru

J.i8:ffim - sodtum sulphate

+

-.*,too''*

f,

9al+ +H,

(D) Reactions of Chlorides of periodJ Elements with Water

h Refer.to the extra h andouts

PI

lY\la,( fl?{

thls ^sf 'i,* N^+ foa'tt*

r

d"e{

ts ij

n'-( a'?'-Q

w'etA
d?,v"-

rt

y,\otrYt

'rcT

;l

Tunku Abdul Rahman College

Prepared by Choong SH

Schoolof Pre-Universiry-St5dies

a+

frr0e
-Solrtion
addh(pH=3)

^erdqryzYb3*k'] foin
.SiCl4() + 2 HrO(l)
PCl.(l) + 3 H2O(l) PCIsO + 4 H2O(l)
2

of aluminium chloride in water is very

SiO2(s) + 4 HCt(aq)

lAluminium chloride is relatively small but highly charged

Al*ion

DErws eis away from its surounding water molecules, to give up H* ions (acidic)

+ H.POr(aq) + e HC(aq) + H.POo(aq) + 5 HCt(aq)

+
3S(s) + Sg,1sq) + 4 Hct(aq)

U* .r

)).1+ (aq)

-[Al(Hro).t3'(aq) l3ct- (aq)

S;CIO

2 HrQ(l)

+ tnr(Hro).1rr*)aq)

+ilq)

''*iol
4K r\6v\

srhur

Al2Cl6 (s) + 6 HrO (l)

Al(OH)r (ae) + 6 HCt (aq)

S*{

fury
"t
oxid

+lrcb+

vuater

) yl\ + ai,d

fr- t*t
6\ wq.il

(t1,0)uJai
*:T.6*.*:****:*:*..*,".,-

{aQ

q*nr *r1ry { *rd;j i,i.{ {qt (u*1sfttt)J't t"c1,) + H c*t }

*lrront

r C,l- + t -Y\^&rld{.

+(

cts(s) |i$'o (1")-> qi1H),

h

{qq,)

, Sna"t(

qqJ rvrf)ec{k

+ B Hcf(sq I ,)
uJ

!.V; 1" }ivc "p ' 111 tol,"^rd

tJta{

-+
(r@_
v

Nl

a'" S, CIJ

? Na*s*o;

@+ ,L\
IY" \4/

Na, 56

r
(rro11
Po

NaSO/ *D + No,SO:

0,-J

rt.,

s,#0

{'-t
Tunku Abdul Rahman Colle-$ School of Pre-UniversitY Studi

--\r

r',\

Na

Prepared bY Choong SH

^-*--/

and water (A) Reactions of the elements with oxygen' chlorine

neaction with oxYgen (Oz) r,,t\rrt * i,\r\1(c,b. + ruE{r\Sf Reaction with chlorine 2Na +Cl'z

Reu"tion with water (HzO).

Vt

yerooJc

fbe) F;; ionic oxide tv"\"Q-) i Jr{c-t rO.r i [LrO*

Ztittg+

Tarnish'es in arr Bums on heating

l-t'*

rd'?Mm

I L,dfua,
ZNa + 2HzO

-' i*tiI ai'r#ar

2NaCl
t,C+\ ct{rrrdl

---+

'v*11!t'ldgg&j 2NaOH +

Reacts on heating

(lfffiHr'

tY""* Forms ionic chlorid"@

iolent reaction at room temppraq#e,t&g\gfl rrr"trr g#s65EH

swfa"{w'ous'

x'

H2 evolved, alkaline NaOH

Oz-

2MgO

Mg +

Cb-

MgCh

trrfgr+

HrO(g)- MgO

+ H2

Layer of

#sb'
ffit-t

MgOffi Yft

Reacts on

heatingfu@@

Forms ionic

chloriaecffi;

:lu8*pry

Burns with brilliant

R"u"tionuu$iMk&.,
(g) H2 evolved

ionic oxide 84$i

4at+3Oz-2\lzOt
refu6a'

7et+

3Cl2---, AlzCia

2at+ 3Hzo(g) -+ A12o,r + of

chloride . Forms covalent Layer of AlzOr fWW (whrch'vrlT't-it 4ru {xl

Burns on heating Forms ionic oxide

Hz evolved

Si tllOz

+ SiOz
Forms

-- SiCIaU)60\ovrrl
Reacts on heating

si + HzO -+rtrtfir'ffibttbn
Irto,

No reaction at room tmpffature Brrns on heating

nesetbnulvitlr,'w&ea+*

Wffielffi{flg

Forms(ffi#H&

Tunku Abdul Rahman College School of Pre-University Studies

Prepared by Choong SH

P4 +15p2

P+Oro

Pr

+ 6Clz ---+

P+

Hzo=,{ffi#*ffi

urns on nealmg Forms covalent oxide

PCI^

-;.t^

ffi
Ug ") if
S+

\-E ut'1w. sott6/

-.|lliE

Burns withffiHiltBto give sulphur dioxide

Ss

Cl2.-ffi;
'

S + HzO

iS vud)a"u{.c

-{ffi16i6r

*mnMinUt*

No reaction with water

zffi
* U tDot4ld+ rta-* diutclttl ,t*4h # hgo* rdou q vYIAcl'
huo
ar^'/
Flame Tests for Metals

..\..Wideo\9. I The Peri Reactions with Oxygen

Wideo\9.1 The Periodic Table Sodium and Potassium in Water

Tunku Abdul Rahman College

School of pre-University Studies

Prepared by Choong SH

(B) Variation in Oxidation

Diasram __<_

Y tYda+w. nu{nbr4 "6 O q4da*oa ^ymfui I arF,rrde.'

r
Oxidation number of Na in Na2O: +1 Oxidation number of Na in Nabt: +i Oxidation number of S in SO2 +4 Oxidation number of S in SOI : +O Oxidation number of S in SCi: +i Oxidation number of S in SCl2:12
Oxidation number of p in p4}u:6; 4-g Oxidation number of p in poQl:"+5 Oxidation number of p in pcl;: +3-

Aicl,(s)

*[ rck 6t

.x2r )+ ft{Cf s

Oxiddionnumber of p in pCts:
Oxidation number of Si in

+i

SiO2:14

Oxidation number of Al in AICI, = 13

3:ffi'ti$::ffi#'i'lh*"'

Prepared by Choong SH

($)Reactions of Oxides of Period 3 Elements with Water

-Ulelting poi ts of oxides

wya

86, /SG
,rnnnnb0r.

Tunku Abdul Rahmancr@e School of Pre-University Stdies

Prepared by Choong SH

fit{l.l

tq-

)f80c=-

fi,c{e

cg)>$"

+lcrb G)

(D) Reactions of chlorides of Period 3 Eilements with water

Element Structure

NaCl

cirinnL;
High

MgClz
.

*Md#m,*,

composedof.oppositely

composed of'small discrete molecules held'

charged ions held together by

ffi'
Effect of water on

t#ffirr$os&*set*"

@, togetherbvffiffi

* SiGh,* |

.14619,

Strong ionic boirdS must be broken before melting can occur Dissolve readily

(memejalwap)

Mim&,

W W *tffi,,
tru
Sen^o,Ii4\

frB-

*tl[lJHtfirtion

: neutral

*lffih-* solution
qw@Uilil}E
Slightly acidic

Hydrolysetffitoform *idi#uffir*

dtffi

ffi

s+Urmr-

Tunku Abdul Rahman College School of Pre-Universiw Studies

Prepared by Choong SH

Some Uses of Group ll Compounds

. as refraclory lining material
-Very high melting point

I
,l

Chapter 9.2 Group ll Elements

-+.loMnducttr
. as a drying agent

as en antFinflammatory agenl

-lo teat

acid indigestion . as a conslituent in toolhpaste conslituenl

toolhpaste

. to make plaster (walls, setting.brok"n bones,

sculptures)

. blactooard chalk - used in concrete, cement, mortar and

ffi &! s%,- "g**' ff-. *lftl #trSs'ffi

X*:"Xf.ff.f;if;e:l;

. used in the blast furnace in iron extraclion (to react with acidic impurities to make a slag such
. to neulralise acidic soils

lntroduction
Be, Mg,

Beryllium
Magnesium

'ls2 2s2
1s2 2s2 2po 3s2 1s2 2s2 2p6 3s2 3p6 4s2

Ca,
Sr,

('liming

used in agriculture).

Calcium Strontium Ba,Barium

1s2 2s2 2p6 3s2 3p6 3d104s2

1s22s22p63s23p63d104s2
4P6 4cllo 5s2 sp9 6s2

. as'barium metal' in X-ray work, e.g. to detect

ca.YLo,*.u*,L

. Valence shell electronic configuration: nsz . s-block elements . Alkaline earth metals . Have oxidation number of +2 in their compound . Contain ion M2*(eg- Mg2*, 6"2*; in compounds

. Physical Properties of the Group ll Elements (Down the Group)

(1) Atomic Radius (lonic Radius) Down the Group ll, atomic radiusf (or ionic
radius)

-Proton number f , nuclear charge I -Screening effect f becadse more number of

electron shells -The increasing effect of electronic screening outweigh the increasing nuclear charge -So, net nuclear charge I -Atomic (or ionic) radius I

- r,,,lV

fo g
D

. t( r\'" -tJ{. -l'-r.a:1i+:& ', t . ,-,. 6\.'o'[,"T(; \ .s r^l ' tr lr(,,-* g

,^

- Ut\t.t\"'\*"'3-

th*'

*-tDtut't

at -{ , '-'/,ot'-'-.r' lt,,\o,.rrr\'

;lIrr"t '''

.'

ri (

I --

IAuSt

Lno"r

+"o tttr/tcl ureh t"'ytth & d ogl*n

Tunku Abdul Rahman College School of Pre-University Studies
Prepared by Choong SH

(2) lonisation Energy

Elemenl
l st lE/ kJ mol-r 2nd lEr kJ 3rd lBr kJ

(3) Electronegativity
Ba

Be 900
1

Mg

Ca 590
1

Sr 550 1060 4200

Down the Group ll, electronegativity

740
1450

500 970 3390

I
'

molj
molr

-Atomic size

800

150

14800

7700

4900

Down the Group ll, lE I - Atornic mdius t, net nudear cflarge l, attraction between nudeus and eledrms l, easierto remove

I because more number of electron sltells -Abitity to attract electron J

Shietding effect

4,w al6ltt e
4l^L
PJQ-'!"&

(4) Melting Point / Boiling Point

.
lattice structure . The way the particles are ananged in the solid.state

(5) Hardness Down the Group ll, hardness I mqtallic - Because r,.qt+,.,4 strength I

cantv't\ar&r-,i
9r-r^ AoJo@J

*' ):{l'L gi.r..^'yr

r^dat\tc\aOJ''

lonic strucfure, simple molecular structure, gianl molecular structure, metallic str0ntrrta

nfhcflrnrrnll

mn/hn

-)-fz

_ \

5t

,t

- lffi,

Attraction force between nucleus andJ&lscalisedelectron i strength of metallic bond 1

(1) Reaction of the Elements with Oxygen

.
Chemical Properties

1.

Formation of MO (s) Burn in oxyggn (air) when heated to produce white ffibxides;

2Mffi'+ oz ffi;'2Mo
2Mg (s) + Oz (g) 7 2Ca (s) + 02 (g) 7 2Sr (s) + 02 (g) 7' 2Ba (s) + 02 (g) 7

{#
(s)

Eg, 2Be (s) + Oz (g) 7 2BeO

2MsO (s) 2CaO (s) 2SrO (s) 2BaO (s)

ffffil
Schoo|of

o,i*^':l,,'#

;i:I' ;Y^;a
.

,,J^;;,:HIS, pre-unive^irr"si
(2) Reaction of the Elements with Water

urrcrar

-G-iaII4l
)a- \
Eement Reaction with water M (s) + 2 HrO (1, g)
Be

ffi,

gq'"1 1r?, $:
eper-e{:ry@cEH

*"r,Rl
rtgCo4}
.'

-*A
reaction with water) Be (s) +2 Hro (g)

w'll

%? L_!1 " -- -*- "-t{r'.,g bc

at high temp.) (no

-a{'coq;Pas

M(OHL (aq) + H, (g)

React*(ltsxfttffidt!(even

Down the Group ll, reactivity t

- Reducing

strength of metal

1 1 J

Cr,,rCE *Zf,t

wq -"ffiil3t) F<eacrWflflffiiltlp * t0{ O

Mg

ins8luw
+ H, (s)
.

Aag

elery'?fit

feetcttvt\1

Mg (s) + Hro {g) Mgo (s) + H, (g) Then MgO (s) + FLo

Art*'n
So

gmlg

ttc

g.t*fp
616-

Cai{,ob,[

* Reactffitvitr
Sr(s) +2 HrO
Ba (st + z H,o

React m'withlgf water . -Ms(oH)*{S) Ca (s) +2 H2O O CIa(oH), (aq) + H, (s)

af

r^xf,+r

g[d water

H,tti'l
.Ba

$0'.1

O-,{tfifffiIaq) +H, (g) ReactrIEffffifiUroF water

m a{ah,hr4f Wraat ls.*

e*wg'rtt t-

rrl-r*iro)

+ H- (o)

e4;
1,1

Gtoute

hut

%r-'ff
b an rA

Group ll metals must be stored under oil (liquid paraffin)

-.To protect the metal frorn'reaction with oxyEen.
and water vapour in the air
'

(3) Reaction of OxideS with Water

Dissolve in water to form hydroxides MO (s) +.HrQ (l),

M(OH), (aq)

tmilmipF .ffi

. ffirtitryffirfis
.

hgalroXrdr
MO (s) + H2O

,* a*1y.,)t$v *'auViiS trdorn *uP

(J
Reaction of the Elements with Acids
M (s)

O -

M(OH), (aq)

.
. .

MgO: slightly Mgo (s) + Hro

sohElg-

2 H* (aq)

l!t2+

(aq) + H, (g)

cao:

srisntry

CaO (s) + H2O

solu;e (l) :

(t)l-1lvts(ou)z (9 , _ P'H=g ^(?*li'*

Ca(OH), (Q) limewater

Sro: soluble Sro (s) + HrO O

BaO: soluble BaO (s) + HrO

Sr(OH)..(aq)

Be"hds no reaction temperature Ms (s) + 2H* (aq) Ca (s) + 2 H. (aq) Sr (s) + 2 H. (aq) Ba (s) + 2 H. (aq)

vr,iith

acid at room

+ - Mg2* (aq) + Hz (g) Ca2* (aq) Hz (g) - Sr2* (aq) ++H, (g) - Ba2* (aq) H, (s) l

Ba(OH)2 {aq) strong alkala like NaOH

Eg:

Mg (s) + 2 HCI (aq)

MgC$aq) + Hz (g)

ha9

+t-

lrlfittc

il^t)(W
t!

9D

n0 req$nn

Bsc

rtv,*fury t^ti* r*:'!)

t-s*Iilr.rL"h 5*r ftrJA <+\bi

c

1 t t {o recrst at,dattt'i oodlr high'c recs*aqA'tb PernonT+ ,h^,,Wj! pnra,i., u,tsal bh taa*Ofie Abdul Rahman College t t Tunku
Schoo I of Pre-University Stu$ieo!,^

Prepared by Choong SII

bt

.
,.

Thermal Decomposition of Nitrates

All Group ll nitrates decompose on heating

tvts(l'JQL (s) 7, MgO (s) + 2NO, (g) + %O2 magnesiw nitrogen

oxide

(g)

Easv to

o""6fiboeirl

diox

ide (broM gas)

Ca(NOJ, (s) 3 CaO (s) + 2NO, (S) + % Oz (S) Sr(NO.), (s) 7 Sro (s) + 2NO2 (g) + % Oz (g) Ba(NO.). (s) 3 BaO (s) + 2NO, (g) + %Oz(g).

r-rarato

Thermal decomposition decreases doum the group cationic size increases, therefore ils polarising power decreases.
the. shape of the

bJffiJ*"."
allo!
.

tlote: polarise: to pull electron and cfiange

polarisation: cation:ftigh;dEfge,
small ionic size anion: bigjonic size
'

*tq :*-.e# cl, (s) + l-l>u ) _> Be ge o Cs) +t+cl. 1' a,^a\Dtortcf -

ffiT*r. 2hHi#'i

r::;[] ;'*';:; ;;TJ,it * '1&i&! io' t ::?t i ffil : :#;jY, I i-i'il, \;;,1''41u" *.:-':: uilm; sr,"v4flwe*t
b6tslL I - - \ a ttt>t fna'l -+ r Q,cl. , (a,4,) + n>-\--lr
+r^{

o L*o(s)+Nadl 'i?oi (aau) ->Mgcl'(a# Lo.'*ll Drvra0 ( s) +) Hct ,, &'k@

^;L*$:ffi,.r; r''t'i'n);:ffit^+'\W
?'ou'' ,doarn
(

( 'p rwrct tT"^,fff1:r9;

fr

fiv*

' "rt,o*@;dTftN" fr-fnttl,), rs)-

lwu 6cdic la m/'r

--) ,r, + * o, (s) > ":r;.:' _ l*0, * t'lbr)-6 ; ca o(s) + ,,.r 4o ( rr(sY .* 'N::g.' ?i;tYl", Sr ( No*),er ' + r*o;'/,,){},,i'*?

e) + lo-

cs

4 *:Hi,: :'
\t\-/
<(
NU,

r^\ ffi-; 'fii JI

/{\ 'bo')
+
id,,r

^oG) <lnoto(dt'lh bP' bg,Y Cutrn t s*o '

::].:

ehrst^ u\ne

-f r^^T*" y:;;hb,,v'4niiNa-

I \l
Nb;

ah;rd furiocl eknoat

----rwttus racfiuS
aAG

Date:

,al *lrrr,k

l-1

hnr+

le

efucln o*lu

4 n4dofrr^wnbil S inYtlr S+nl

pwbn

Jt ydoo nuubor * nltd@r da rye

Dou>ft A

t nct

*ld
cln

x *raninl "{fA * nd iltd.oar

nucleqw

* atlactjn "utw aT,nu,chrs

,i.5k4

car

+
"F

atn

lt
-rVa

railiqs

Jt acass

*l

fnLq

,t
x.

gta
no.

nudOar

gpecio"( oesc

P,8,cl

1o-

8i

*l .
n

:,f

-B

)P

Tn

;F rwmber

* e- ih

,yt6)ecuU

j[

ehell

r+iu)

nu'n2fi| - ffraP h ( Wtaul' nelatlfto{ - dclocalitwl e' ifu .Q- cbuc!

&Eu

nude-nr

ak

qtas

"l

{t srr

ile
'*
zdtol.

flict
daar

odd

--

fi4 p>uf

IE

>tc { *t
3

?henical
E

fu"
'6ir

Axdos lPwcf,rn

^irth

0, lcl" /H"o

Elenertf urth H,C & (ondqg ultfl,- firA

Peact;rth C*
rnobt/non'r,Cb.l a

A, 2

ori:le

eler*at

& tO, +

s,4t

&,O*

Si-'r

@ s*d, +

sd-

CI, *<tal non't*ta/ +C/r) Ai tcl" + 4lz

notql chlod&
PC,ls

'nonqnota,/

eh/dtv

P'- c,l- s CL td excess PcL + cl,

Clz

B+

cJ,

4 J','C,l-+
hl'.A

) Nls
.Sl,.

uth
mOtol

>c)+

P+*[O4 X

x
x

H,O

-2

neta(axide

fHn

ll.O -+

lbo'

///

Rxn

O,

Q-)scl

t,fud^N/

L afilh aater
q,C

&.C ' ) ntf a -) HsF+

30,

Os

rv

naY

satuble s4qht

A'> H,8,
-

$SAs

non

4ll

n<-to.-l urde are sdltd Qece#

tl.A + 'nebl + flr0 + acl{

55>

ft|"&

rtonc di& + 1*rtc cxt& +

/,sve

dll- +
bil>lh rcicl

/bs<

+ Naorl ->

N"fiLl -->

N+ + H,

+ H-0

4"

cs) +

-F 4 alrt illqilq

l-4e Ndfz? mlle

,qU &q(

olarl&. 7t4p aunudl

,iafer , alg t'l.on nlla-x

to,

0 ) SrA,'(4

q Pds { H'D +
Scr, f9"'\,

-)

tl,

P& -rt fl-C,l

t'

HCl

q<

a
No.:

Cst slott
a-fb

,f

kA rxa

&^
Date:

flftnic'radiqg
iso4irn

-u_

Q;ide ^,tlh *, tYl}k) H.oC()+ tutcail)-U

- 8e O rs anphotoncr,oher

atQ

tfftnic,fu

-jQt &u *o

Bp

(insofu Ate

*MlW h aflai edi,at

M.nuderc
4pficrpttix en41o11is

g'tel4;tl

e" S,

@/i7h1{y s0+,olz) O (so/,bts ) &O ( so/ublz ) .:frtrq a/tq/l

A. ktisnfu 80qbu )

BpaciTon

M G) + 4t@)+ ek k lAo oa txn aillh acid a* nL

(L-,; <^i i -i -r r {t

itll

d-arl

l^/-

henlc*l
M @S
rfe glid 6xi4! (w rsrtO

O"

/t40 (b'

'

+,PtluN * Therwa! docaaoasifun ard Ther,rat

skrFrli{v
ic

{Ul@ +

H,jU,q)+

l4(or+) a rln

srs)q
nait
lnr. 'ude

)q a {CAl +,( co+-(ce)

_>

*I
'bcna,tes

T,

fu6t

a?

n ,n I

0'

4,

H"O frl ai"

,fi

Prated

it

tt
T.

dcu rlr ,.so I

aod @>
stabili

8e

becoqlP

tbQ

frnis h

)*

Polal1g,

a+irr: frractll . hbh chor5f

To Pur

0-

h s.qrga :

Tunku Abdul Rahman College School of Pre-University Studies

Prepared by Choong SH

lntroduction

Chapter 9.4 Group Vll Elements

F2 fluorine Cl, chlorine Br, bromine lz iodine . Valence shell electronic

.. pblock

configuration

ns? nps

elenaents

They are called halogens Non-metallic elements

,h2ili5 li rre iirl!5:ia: !5. or.:r.,ji.ma! iilc ih: x*id.il@ na;ir3J:5 siid B rh. listi. tvf,

Physical Properties

\
1
'{

Siii-r

ar{id:
h h.

*E+J*i:+. iri n$

&. ai is{ .i !ir5?9i.

i.,u.iiin

Colour & State at Room T

Colour & state at room temperature

.
Solubility
ln waler In sganic solvent (69

Colours darken down the group

,l

b.p/

cct.l
F2

All halogen dissolve slightly in water except

F2

Pale yellowgtrs.

WM-.,1

,"WA

188

CI, Yellow-green

Br, Dark rql liquid

ffi: W"%,t
t,

-35
58

qsdlfiir
sotuble

rryffi

soluble: yellow solution soluble:

slightly

12

Black

sdftd .#

ffi,I
183

solirl{e

orange
brown

- Cl. is moderately soluble

solutioil

clz (s) + H2o (l) + Cl-(aq)

in water; turns litmus paper to red and then bleaches it.

'$[#tl#soluble: purple solution

insolutl3

ffirH*(aq) \l!r**ry--l

\---\

--..- '-t+

Tunku Abdul Rahman College School of Pre-Universitv Studies

Prepared by Choong SH

VO I ati

itVq' , (

lrer-eruawapan)
Ease to change

Down the Group Vll, volatility

{-{tj{l_^
held

- They have simple molecular structures - They exists as diatomic covalent molecules, by VDW forces;Fr, Clr, Brr,li: - Size of molqcules 1

Number of electrons in the molecule -Strength of VdWf f

B.p-

t
J

-Volatilty

Physical state: gas

lkluid

(F},Cr) (Br,

solid
(lz)

(1

. All halogens are oxidising agents . Oxidising power decreases down the group Chemical Properties

r{rttHmry?s'oxtuisiiig

A$ei1r

lt

{,

Order of oxidising ability

FzrClrtBrrt
strong oxidising

l2 weak
oxidising

agent

agent

.f1\\ rt\\ telLt\ I

L,^

r!"'- , *

W\k +W'il' PflAar

-V*t{$t'-'ku'n -fr(

I=

,F' s0i

X, (aq) + 2s-

:
-

,x- ,, lDephcc.
rxn

Chlorine can displace (oxidise) bromide and

Bromine can only displace the iodide ions from its aqueous solution.
Br, (aq) + 2l- (aa)

@. lb-'
7'
ol-t-

ltD,-

iodide@frcim their aqueous solutions:

Cl, (gI + 2Br (aq)

lz (aq) +

2Br

(ag)

C[

+ 21- 16o1

Br, (aq) + ZCI- (aq) l, (aq) + 2CF (aq)

l{edog-6n c*ifi aixidise the hande to-n

{rq),6eb$rft.

lf the resulting solution is shaken with CCt4 (tetracfiloromethane) or any organic solvent, - the kofiine liberated rvill colour the oroanic laver o-dnge+.wr1

.ehilt ct uitl colow tPdte

-$^( "t?l. i'n(q:[,r. ,,.'tl
ex'rt'

v*

bdrle v/ill colour it violet.

thtt,nol dlr,urr,.t;lltcn

+1b;('-t1,

{o brAak filr

h^r(

tffil

t6ffi \w2
.

Tunku Abdul Rahman College School of Pre-Universify Studies

Prepared by Choong SH

All hatogens react with

*\ 's *' lJ s

ti,$l**,$-zrii<$ Hz + Fz * 2HF -' {t*il;,lFlutl?8 'hidrogen fluoride H2+Cl2'*2HCl (rQffirtfiiuil,' hydrogen chloride H, + Brj'* tfl$1 rrrffiffiniltFt)
Hz+lz#Hl - - "HF, HCl, HBr, Hl : hydrides

The covalent bond in the Fl'X mblecule is

llfw,sirgng.heating.

-, Hence,
.

trr e

needed, reaction is reversible)

*ffidde

depend on the H-X bond energy

Wffiil$.r&+;tJ$Uffi

$*fr

*,

& 1u^r!zk
Bond Bond Length/ nm Bond Energy/ kJ mol-l

ra,t{ilt

tbr -,^^( ttdfry

H-t
0.142
Covalent bond is long, weak and easy to break

{ -^thl
.
Down the group - Strength of the H-X bond
group)

H-Ct
0.1 28

H-Br
0.141

Covalent bond is short, strong and hard to break +430

+370

+30Q

@ -rot=s661q*
HF is a.weak acid because: . HF has the higlesi bond energy (H-F is very strong) nF motecuies make ionisation

(weaker down the

Down the group - Size of the halogen atoms 1 - H-X bonds becomeweaker - Thermal stability of Ft-X { - Thermal stability:

I:l:::,*:f$w

rnffim
*

ffi

QE[FliEbte

L\ Au-l, ^r& 4,\

The halide ions are F-: fluoride ion Cl-: chloride ion Br: bromide ion l': iodide ion Slver nitrate solution, AgNO. (aq) is used to test for tese ions

- turCl:

Astr(aq)+"',(ro)ffiffimft
ammonra soruuon, NH3 (aq) rororm a

rgG ilIn

tffi

tAs(NFUr. (aq) + ,mplex ion

(aq)

ltet

,d
C)

fu':-n',
y,(:T:^r,

rl

'. \(0,"T1,*l\1T,1'
WrT;.,r.,h

=.:

i,:

Prepared by Choong SH

1.
AgBr (s) + 2NHe (ae)

.-

\Iy'hen chlorides are heated with conc. H,SO,, ^ white fumes of HCI (g) are given off ' -"';4 NaCl +

tAg(NH3)i- (aq) +'Br (aq)

H.SO

t&I

ggu-1if

white

fumes sodiumfiydrogen

ir*E-EBH|F ^fr'.,.@nnmo|Ta. solution : nuc\QQr ah arfljaQ

-i{fle#rg6B{Xffiffi b"t HBr (white fumes) and Br, (orange brown :" rumes) are oiven off
2HBr + H2So4

u:-ry*
3.
Nat+

-i!-' i' 'i

lrrf,t
With
qg!=d

faAW

Flr5o4

+ Sa,

When iodides are_.,fteated with

2Hl+ H.560

Hzsor{fiffi;
-lFlffirr

(6) Reactions of Cl, with Alkali

and dituted NaOH (aq)

_1 0 (o)*LffiilUlF,iUlf
ox. num.:

(g) + 2ttaot-t

1aq1

lr"dtfrq) - traclr laql *sodium + Hp (t)

chlorate (t)

ox. nurn.: -1 0 Note: Clr: yellow-green gas Brr: brown liquid/ orange_brown vapour lr; black'solid/purple vapour

measn Cl, oxidised to NaCIO aod reduced to

N#i

'

withtgland-qgleeotrat$t NaoH (aq)

Uses
F, fluorine

- 9I9J: coolant, aerosot propeilants - PTFE: (feflon) non_sfck oans - Fluoride, Fin tooth paste
3ct(s) +6NaoH(aq)

il,-,.^.-1..--l-r * ru"[b,1aq)+3H,o l*s sNairiiqy

redued to NaCl at the same time.
lt is oxidised tc

Cl, chlorine
(t)

- PVC - Bleahing agent - Disinfectant in water - Organic sorvenl gC!!, Cfblr

Br, Bromine

ItEErg(EsusprtwluHl[tfr,.
NaClO" and

#S"**^1 t* C5J R^^ 'f

- F-,t et - t",.n + rc-dtct - br- rgd,^o H"So+ -lp s0. . lh Proalss, 9r^. -ox',tcliv4 't" *rL Za o xi oJist d' "(l z' rudqe r{rBo+

i^-tm6
+
das*
t<tW

- Pehol additive:,1,2-dibromoethane - Silver bromide, AgBr in photography - l-lame relardant

.r*ltlJ*e

Tunku Abdul Rahman College School of Pre-Universiw Studies

Prepared by Choong SH

lndustrial lmportance and Environmental Significances 1.

Bleaches for cleaning clothes, etc.
Chlorine is harmful to environment and health To make bleaches,

2. CFCs: chlorofluorocarbons

dttffifrra{dffia

-Jtgiltpt
babies

- A&Ddtxffi*ffi$fter and birth defects in

ln water: kills fishes and other animal life

_ Uses: - USeS: .,0. Refrigerants (refrigeiators,

. (b)*enrud6B@4i6f86flttic) . (c) volatile . (d){smffifi{tillfrfr.rt

Why are they used?

(a) unreactive or inert

'

air-conditioners)

Aerosol propellants (spray cans) Cleaning agent (solvent) for electronics Fire extinguisher '_rxetsxullgulSllet

Environmentalhazards
Deplete ozone (O.) layer in atmosphere

1g,6Ld.

;#wf

l":;X*"*,,

eye taracr

Damee tovegetdion food trops

F'Ozone depleti6fi'

'* crcl' +'

a

c!
#?

.
.

03 protects us from harmful UV light

CFCS destroy the ozone layer. - CFCS @nlaincl atoms - High in the atrnosphere, CFCS break dM to prcduclfree radils, Cl. - Cl. tree radicds breat< dowq1ftffi.

f,f,m.

c{'
c.la,

v?

-?

LIU'

*r

./-r

:flt+6#gi6to8+ o-

Steps to protect O.

-e1s",F&{UHfo"'

I 0

-+

(:f . +

o,

fay"t

Use LPG (liquid petroleum gas) in aerosol spray cans Use HFCS (hvdrofluorocarbons)

cl
I

-ffi

a*ora
'[

W)
Az

rCqF, 1 ,cl

.Cl +
+l
tr*
r.-l

,cl} + o
2-j*T

V U,(

+ 0, + Clo, -> 0, +.CI c\c

-+

C)n / JU*f

f"

[1n,

,lc*

{;t -;7 {'i{}. -' ,,. :7 {t"' {-t t.,

i,"i 'r.-'r

Proy

Tunku Abdul Rahman College School of pre-Universify Sfirdies

Prepared by Choong SH

Chapter 9,6 Nitrogen and Sulf :;ur

Nitrogen
t,

S$rfi^r

Ammonia, Ammonr iunpion

N{r
.
Very unreactive

The N=N triple bond is very strong and very hard to break

,,f-u /i,4*J
p

-^S^oreaction involving N, have a high activation

energy

ammonia, shape:

Note.: we have to use a catalyst to carry out the reaction or high temperatureirO n,gn irJr"rr"
3

Flr

NH" , I c'r"rd erl

bond angte:

1r]

I snape: i*^ *'ia' t j oono angte: tol,5

%','
lY"t)

amnronium ion, NH,*

ri'l
l'"

a(

Formation of Ammonium ion lh9

Ht ion
NH. motecute forms a dative bond with the

Reactions ot

.
J fl., *+

with bases t"g NaoHi-r

""4

LI

q *rl;iN?HJ fl r i
i,rhu,
brlNd

eg'

On heating, NH. gas is formed

NHo.!\+ NaQH.* Nact+ Hrc + Ng.

.,1/

fr'*r"{4 A:.Use.CaO (calcium oxide)

g'.To*-oo

*"'1,"",

w' $)

Eff#.&&r-,rte
.
lt will turn blue

Js a drying agent. acid wi&rcild--#-I$i**s,,

To test for NH, gas - Usea damp (lembap) red litmus paper
6

,{{

grr,+9s4(

Tunku Abdul Rahman Coilege School of Pre-University Studies

Prepared by Choong SH

The Haber ProcdssNz(s)

Operating condition s: N2 and H2 in 1:3 ratio

* enrGFlzNH.

v40 (s) asellffi

Prtnrqt
'

lndustrial importance of ammonia and its derivatives

Eg, (NHo)rSOo: ammonium sulphate (NH4)3POr: ammonium phosphate

1. 5.

v\de{ ch^fuliw

2. 3.

m
!--llw

Temperature:45O"C Pressure:250 atm Piomoters: K2O and AIiO.

NH.NO.: ammonium

nitrata

Principal involved: 1. High pressurc beca use the forward re action produce s less

2. NHs is used to make nitric acid, HNO. 3. Liquid NH.: refrigerant

. 2. 3.

gas Hioh temoerature io increase rate of reaction exothermic) Catalyst: to

moleculgs

udu^wdru rEdururr

,.";*rs

lore r E" to increase rate of reaction

5.

Aqueous NH.: washing and cleaning HNO.: nitric acid: to make explosives

NHt '- 7rdtN

# ru[a \ ll,$0+ *
*Jilr0orn&u{fo?

is*x

^ coag4orial .ry ,expar+el 4 lr?yid

fiW,

CNI{C, $o+

ad

awwOttu# s/ttt'
oNLY

Environmental consequences (kesan2) of fertilisers 1. Fertiliser: added to thg ioil to increase crop yield

Oxides of Nitrogen
NO: nitrogen monoxide NOr: nitrogen dioxide

2. Overuse of fertiliser: will cause eutrophication - Fertiliser will get into.rivers and lakes - lt will cause algae to grow rapidly - Algae will cover the surface and use up the orygen lr the water The concentration of O, in waterwill drop and other plants and fish will die

They are formed in car engines

- When alga'e die and decompose, they will also use up srt' _tt
-ce.Etr*r{rqr$6/lE:{

Nz (g) + O, (g) - 2NO (g) 2NO (g) + Oz (g) - 2NO2 (s) NOr: dissolves in rain water and causes acid rain So, cars use catalytic converters Diagram

Gatalytic removal of oxides of nitrogen from car engines

1-

Oxides of nitrogen as pollutants 1. They form acid rain when they dissolved in
rain water H20 (l) + 2NOz (g)

2-

xpars are fitted with catalytic converters

'(i) oxides of nitrogen are converted to N, and

o,

HNO3 (aq) + HNO2 (aq)

nitric

(b) CO is converted to CO,

acid

nitrous acid

Ehbtnr.
3-

G;

(g) + N, (g) Cars with catalytic converters must use

fi3i$96,

2. 3. 4.

- l-ead b deposited on the catalyst - The catalyst cannot function anymore Tl* catalyst b poisoned _
t

They *itt to so. in the car + Oz (S)tg 2SO. (gj 2SO, (g) They cause photochemical srnog (in polluted cities with many cars) They cause respiratory problems (eg, in people with asthma, old people and children).
'12

e$ffio,

4qArtrrL
J

fiYt / ruLi*e
I

tt

, h6ln, -&^*^"k ra-ic{ rr-i.t

&

I+hn'u"'r
sil-.1. lr

#f
,*

-$1^r\rrL' '4F

Tunku Abdul RahmaJeolbge* School of Pre-University Studies

{iutI 6(rr dN, i t - dn,fnr Arf-i; Fq \-attn{ ltso4 '{,0,., ,,--/

Lr
'9

-\

--'-\ *r,"-*--'

Prepared.by Choong SH

Sulphur
Mixtures and Compounds

XLI-I.

Sulphu/
1.
Fuels (coals, petrol), volcdnic activities

Effects of acid rain

Lakes and streams become more acidic harmful to fish a nd aquatic life

2.

contain S S burns in air to form SOr, sulphur dioxide

a.' Oz *

SOz

Consequences 1. Forms acid rain. When SO, dissolves in rain

2SO, (g) + O, \ + 2H2o (l)

Damage to vegetation (forests, food crops: Causes corrosion in metals (eg, Fe, Zn" see" in bridges and man-made structures like buildings -- destroy marble, limestone. nwa eg' CaCO, + HzSOa + CaSOo + QQ, + ;[$ Destroy paint work
11,c,1
I lectch*$ fl^]t'Lcra 5 " '''"';'-' :'q.,.\ req4t AJt{h m'rfior4.l rn srii t: '' Satt

2HzSOn (aq)

fo"tLt
_

Jia + O, ).so, t Ho_O J

There are 3 stages: (a) production of SO2 O sulphur is burnt in excess air

H,s%

- k ,. resukz $af

laqb

The Contact Process - to manufacture H2S04 1.

higher pressure is not used. YieH
atm.

"i"ril}|

{D)

oxirarbno@sr*7,

S+O,*SO,

2sor+or.-2SO3

'
AH=-192kJmoli

$6;:nof

stlhredifrtr,0&frillry

SO.+1116+H2S0a
reason: a lot of mist is formed

,::

catalyst vanadium (V) oxide, VrO, pGssure: 1 atm EnFerature: 450"C (increase rate of reaction) prd'JCion of HrSO, in concentrated H2SO4 to form oleum,

,lftgF*r*

tlt dr d * eYOeSS a*,

X l,'t{ na :'''l)(fLffe ts Jred e Pu4 r![r' C Srrrgct ird 1o rerrto* *P*!. ei ir , it dtl Po'sr +r\r :Jl:.i'g{
{Bs

SQ Ql + 6.50. (I) H2SzOz (l) err ts,.-5d with water, H2SO4 is formeci Gtf-E-=rr--) +UB sQP +) +rt8'

.\rffsrtt

S vr,ill aausc +he prcducno'' 4 .l E' H=So* nrjSt- 1W mlsl 5 errr66fr?*

{he rxn h*

86o

t1>O

,< i6rr r! :ffi"

tb 6nkfr I

.t

catalyst iS add when 'tsbaihm 5b- E0,

t'

''{H';igi'ib, "l(
& PbS

gs'rrot 99 G| ** S' B*;rnrn3 rnetd

(s) + 3C'

-''

J>c}

-> ;3J'r(!)

z'Ccs> '* (-s)

*l5"O

u''

b,,ltl',n O,

rf

-: ttl

Yr' -lt'

Vurih lnrch

Tunku Abdul Rahman College School of Pre-University Studies

Prepared by Choong SH

snlfuft "," 1- Fertilisers eg, (NHo)rSOo: ammonium srilphatc 2. Detergentandsoap,?'P fr*l ' 3. Faint and pigmenti (eg, BaSOo, efSOopD 4. Fibres (eg, rayon)ir]e Wk(,

ro manutacture

"Y;"i,#J:tffi

or4 '

rq'

v.

ac

id' H's oo
1. 3.

Use of SO, in food

SO, is used to preserve

2 Wine

Dried foods (eg, dry fruits)

Meats (eg,

sausages)

n#p,
aa. -

5. Paper 6. Dyestuffs 7. Drugs, pharmaceuticats#G **h 8. Car batteries (electrolytelg{I3 4$ 9. Cleaning metals before electroplating**)ryf{

SO, also prevents browni/ng of food

V u

aidaltrm Efi ofbur

air

m n7t

so it is added to fruit juices as an antibrowning agent SO. inhibits ftalang) enzvme activity

SOr$ a

rt"ductrng

^Xut

Ju lfu
dn
.naf

Salfur
l

far

Snlfrrr
"s^llur

&tr

$td fm,"

*wtlar

salftrr e,'l{ur
c,"l&rr
Julftar
sral"fu

sIA,fur gd+u/
,s*hrv

sul$^r

ad{"r
sulfu Sut$rr eIF{t^r

Su}|trr

.rdtu/

sul&r

t
ChP

fusc.

;f
(a

N"t

ekcrro$sa

, lM)
aa"r

rnHs rtns is

asF ta f,^tz fl" 4 '

Nrb

FPRTF
N"

) (Lr;w <tec{a;r"rO qt s-/e. / .^tia) \ +4. e1*A?* 4 '/n* 7'"a 4

t )e 4

)o,q - Gd + ll-$

,;+

H"

t /V'- //X

!.!. r

Nu '/x
,5
-,.

-i

ri
r. ll L1 rt6
rl /^ LHl)

ia,
g

T;

L::

jv
,}
C)

t,

e-1 i

r)

\,

SA;;$)O , * So' --) -ll'S+ S}Oi + 'l-f,..,*

ffi

- *i.'

'fitle't '"'1h
l.\

c''ta!fit

(aY

Fnn*

N, + ot --> N0

^tD

{C:*

N0>
e{O-' + &'

c{, + Dt -)
n'rt'r

t h'c 1 ftNdl + N0 Llt! {6a - N6"