HH

1 &
(
-

c -

c -
C =
C
-

C = - R OH
-
R -

Y
/

Hit
&

alkyne c-ynes alcohol (-oll nalogenoalkane/

alkene -ene nalvalkane
alkane c-and
chalo-1

19

M
G C C
Il Il Il H
,

H y
C C n -

y R

' ROH H
Ra
aldehyde -all Ketone (-one) carboxylic acid (-oizacidl eder -Oatel amine <-amine R- N
-

R3
G

C Il

R-CEN Il

nitrile 7-nitriles
a "i
[
! NHS
amide 1 -

amide)
acylchloride <-ylchloride

no. of carbon stem name

meth-

·
naming ester
eth-

Niger vic acid + oate / ser 0 - oate prop-

but -

ester : alky
I

vos
-
alcohol
rate

voc acid & oncona

acid
G
7

S
Pen
Oct-
↑
9

18 non I
 Terminology
hydrocarbon =
compound made up only Cand H atoms

homologousseries =
same functional group
=> same general formula + same chemical prop
.
saturated =
not contain c =
c or c = C

unsaturated = contain C = c //C =C

N
homolytic fission breaking a covalent bond in a way that each atom takes an e-from the bond
= to form 2 radicals
heterolytic fission breaking a covalent bond in a way that more EN atom takes both e-from the
: bond to form
negative ion
free radical =
species with one or more unpaired electrons and
leaving behind positive son
n vcleophile = electron-rich species that can donate a pair of -

electrophile= electron-deficient species that can accept a pair of e

electrophile

tes of reaction
& N
a
curly arrow =
movement of e-

addition two or more molecules combine to give begin at a bond

(Add) 1)
single
a product
=

or a lone pair
substitution=
Isub) 2)
replacing an atom or group of atoms by another of e-

(Eli) 3) elimination = small molecule (e g #20 , HCl) is removed from an organic

.
. molecule (nucleophiles
IHydl 4) hydrolysis =
compound acid/alkaline)
is broken by water (or dilute .

(Con) 5) condensation two organic molecules join together by eliminate a small molecules (e g. H20 , Hell
=
.

Oxidation Oxygen is added /1 e-removed/ Oxidation number CO) represent one atom of oxygen from oxidising agent
i &
=

reduction oxygen is removed//e-added // Oxidation number f

=
(H) represent one atom of hydrogen from reducing agent
hydrogen is added

Mesof
isomers

~
3 types
& structural isomers =
compounds that have the same molecular formula but different structural formula
1) chain isomerism -

same molecular formula but their longest hydrocarbon chain is not the same > caused
-

by branching
2) positional isomerism -

position of a functional group is different

3) functional group isomerism -

same molecular formula but have different functional group >

-

result in very different chem prop

② Stereoisomerism =
compounds that have the same molecular formula and same structural formula but a different arrangement
of atoms in space dre to presence of fl bonds
~
need 2 different atom or
1) geometrical (cis/transl isomerism -

restricted rotation around double-bond + group of atoms

atom in
have chiral centre which on each
2) optical isomerism bonded to 4 different atoms or
group of atoms =

7 -
-

two different optical isomers enationers (mirror image of each other(

-

enctioners non-superimposable
Ps I
-

are
-
.
vin --
/
AHCH
chiral centre = carbon atom that has I different atoms or
group of atoms attached bonded
A &
H
>
compound can have more than one chiral centre HyCCHz OOHC
r CHO
-

mirror
functionaa

Planar tanaries have all their atoms in the same plane => linear bent , trigonal planar and
, square planar is

sp3 hybridised carbon = planar

- · -
-

bond Ofa bond hybridization

type of covalent bond no of a no .

angle
g
single I Spe 109 50
.
tetrahedral
double 7 I
sp3 1288 rigonal planar
triple & 2 Sp
o =
2 Orbitals overlap end-to-end
# = 2 orbitals overlap sideways
Hanesare unsatured (contain c-cbonds (latrrated = contain a
c = cbd

· alkanes are hydrocarbon

#Hydrogenation
(Addition reactions
·
alkene >
-
allane (Addi
· or Ni catalyst +
He 19) + heat
I
finely divided to NCA ratey
,
&
He offe hydrogenation
HH
H HHH
Ha f

H-c-
Pt/Ni
-'c
c H

H= ↓
-
-

H + -

H -
I neat
(Xy 6088
)

· tracking alkene
·
Also y catalyst + heat (noo to prevent combustion (

CHy
+
Gotta >
CHig
-

combustion
1) complete combustion -

excess O allane +
oxygen >
-
carbon dioxide + water

2) incomplete combustion -
limited O alkane +
oxygen >
-
carbon monoxide + water

odourless
toxic gas
+ -
bind irreversibly to haemoglobin

Crude
Ol mixture of hydrocarbons : allanes cyboallanes and
,
are s
fractional distillation
separate by
 Unreactivity of Alkanes
is covalent bonds require lot of heat
·
C-C and C-H a
reactivity +
·
EN of (and H are almost the same
> > both atoms share the electrons in the covalent bond almost equally
4
. alkanes I do not react with
are non-polar polar reagents (
H
no electron-deficient area to attract aucleophiles
no electron-rich area to attract electrophiles H c -

C -

↓ H

catalyst arecoatedona
bt as

H
#of
alkenes H -

H2O
c =
C +

urterox
H H H
alkenes
.

D dids >
-

dicarboxylic acid (pale purple solution ->

colorless solution ( I 'H
cold dilute acd
KMnOy
·
.

& alkenes # de// lif further oxidise to

alden
Ketone carbon aldehyde aldehyde
dioxide ,
can carboxylic ac as
·
not dilute acd .

KMnOy
position of Cin C= C

2 H on C = C :
H- H (0)
C=C carbs on dioxide
>
20

I
-
+...

H H prediction
for large molecule
1 H On C C:

/r-c)
=
R R
-

C =
C
>
-

< +.. carboxylic acid

H H
O O
OH On C C :
=

P
> +, +
Pu
C= C
-
-
e See

me
-

My
 Test for Unsaturation (Bry cage test)
·

Brz lag) or bromine water is an

orange solution
·
Br , lage is used to test for unsaturation (c = c ( = C
,

Bry (ag) decolourises unsaturated compound

⑭
·
.

·
orange >
-

colorless = alkene present

selectrophilic) addition
reaction
 = mechanism + condition

Halogens
Compons ar more halogens
can be produced by :

1) free-radical substitution of allienes

electrophilicadditionoflease
1) free-radical substitution of alkanes calkanes +
-

haloalkane)

Up

CHzCHz +
(12 >
-

CHyCH2C) + HS)

ethane Chloroalkane

initiation
#

and is broken by energy from UV light to produce two radicals in a homolytic fission reaction

M
Cl
UV
-

C >
-
[Co

Propagationn of the substitution reaction in a chain type reacon

& &
CH3 CHz
o() + > ·
CH2CHy + HCl
-
-

~
·
CH2CHg
Cl- CL > +
CHyCHy() + /10
-

:
so on

Seminationinaction terminates are to two free radicals reacting together and

forming a
single unreactive mole e

-&
CHeCHy
·
- CCHyCHy
11> + ·
(chloroethane

-&
CH2CHz CHzCHyCHyCHy
·
+
o CHyCHz-
> (butanel

1 &
(2
·
+ o() >
-

Cl2 ichlorine

2) Electrophilic addition Calkene + naloalkanes (EIA)

·
Hydrogen in hydrogen halide acts as electrophile and accepts a pair of electrons from C-cbond in the alliene
> the product one in which halide is bonded to the most substituted carbon atom (Markornikov's rule)
mor
-
=

Alkene acts as nucleophile

it I
·

i to it
2 halogenoallane (X2 halides
H-
H c - c -C H -
:

roomtert
-

X
H

i (major product)
H
I
IH
H -

C -

C =
C

S
·

propene it H -

H
room
H
temp. -
H
I
> -
H
&

c -
H
10
C
I
-

H
%
H -
HHH
11
c -

C -

c -

H
i halogenoalkane
(minor product

H ↓
3)Substitution of alcohols(alcohol >
-

haloalkanes) (subl
ways : carboxylic acid >
-

acylchloride (subl
1 HX / kBr with conc .

H2SO4 or HzP04
H H
H -

C -
C -

OH + HX - H -

c -

c -

X + + 28
it it it it

Me4) +
ps() +

3 PC5 room temp .

HH
1
room temp.
#
OH P(z > H
HR
-C-C
H-c C + +
- -
- -

i H

4 SO(12

_
,
44
H c - -O
Cox
-
-x +x
So
+ +
-

↓ it

INSI

-
Nucleophilic substitution of Haloalkanes :
Haloalkanes are
very reactive due to large differences in EN

Ot

-c -18
S

I
-

carbon 1
has Iow EN nalogen has high EN
polarbond

>
-
in nucleophilic substitution : nucleophile attacks Catom which has of
>
-

atom with 5- replaced by the nucleophile

1) Haloalkane >
-
alconol INSI
~ by donating a pair of
-

to

·
NaOH (aq) + neat loti ion acts as nucleophiles the catom bonded to the halogen
halogen is replaced
by the
·
Or

CHzCHyBr +: OH
-

>
CHyCHyOH + :Br //CHyCHyBr + NaOH >
-

CHyCHyOH + NaBr

2) Haloalhane + alkanenitrile (NS)

·
ethanolic solution of KCN + heat under reflux (CN-ion acts as nucleophiles
CHzCHiCN
-

CHyCHyBr + :CN > + * Bri

IKCN) IkBr)

3) Halallane >
-

amine INSI

ethanolicsolution Of eeNhtheundersur
·
in sealed container (N acts as neola

clamines
>
-

it is important that
NHz is in excess as the product of NS Cethylamines can act as nucleophile and attack another bromoethane

to form 20 amine (diethylamine

 4) Halvalkane >
-
alcohol (NS followed
by Hydl · OH-

· ethanolic solution of
AgNOs@g + heat under reflux (Hjoin AgNos lag) acts as nucleophile
Her
C2HyBr +
Hy8 >
-

CHzOH +

H H
H
loA
I
5
-

(This is reaction "is" /

-

H -

c -

C
-

Br >
-
H-c-C- OH + Br

↓ Wh it h
-
reaction is is similar to 41 but 41 is clover reaction dre to HL involved

>
-

OH is better H,0 in terms of nucleophile because: Of formal negative charge

carries.
of +

199l
1H20 carry only 8I
· H
reaction
-

be used
=> 4) +
AgNo, can as a test to
identify halogens in Galvalkane
because haloalkanes have different rates of HL .

AgNo , become opaque :

Hy take place

Elimination reactions of haloalkanes :

-

Haloalkane >
-

alkene (Elil
·
ethanolic solution of NaOH + heat under reflux
-

causing -X bond to break

herolytically
NaBr
HH Hyd +

*
T
c
I I
H- c -

C -

Br + Nastcalcohol >
- c = + HBr + OH + Nat

↓ H H
ethene
Bromoethane

S'
-
Suz (NSI substitution'
=

N' =
nucleophilic
i rate of reaction crate
=
determining steps
-

Sul nucleophile attack" t

forming
"
: = donales a pair of e-to c atom a new bond
· for 30 nabalkane
· 2 steps reaction
1) C-X bond breaks heterolytically and the halogen leaves nalvalkane as an X-ion (slow and
rate-determining step
This forms a 3o carbocation <30 carbon atom with charges

2) Nucleophile attacks 30 carbocation

CHA 43 CH3
I
lot 8 slow
-

xX % OH
t - -

Br Br
Hy ) Br
Hz) C CH +

ins
+
Hz c >
-
-

-
- -
-

crate
determining
Step its its
· zonaloalkane undergo a mixture of Su1 and Suz depending on their structure
 Sp2 :
·
for 10 nalvalkane
· I step reaction
1) Nucleophile attacks 10 Catom
· C-X bond breaks
helerolytically and the halogen leaves halvalkane as an Xion

-
HH
Y
Ho
I
Ot
H-c- c -H H -

c
-

C -
H

dit it
Gar it
ethand
bromoethane

Carbocations

more stable
-
carbocation =
higher yield =
major product
because :

effect
*
·
greater positive inductive
4 due to more alkyl groups attached to the carbocation

reactivity of haloalkane
~

I
Bond energY
decrease
down
the group

test
AgNOz 1991
ppt .

↓
Paler
+ NS faster
+ more reactive
 #
Hydroxy Compounds
alcohols that contain at least one
·
are compounds hydroxy (-oH) group
general formula : CnHan +,

Electrophilic addition (EIA) of alkenes//Hydration of alkenes

Alkene >
-
alcohol LEIal
·
not steam (H20 (g) + conc .

HzPOy (phosphoric (VII acid) as a catalyst

↑
HH

c 2011
1
-
c= + H -C -

C -

OH
H H H
ethene steam ethano

Oxidation (Ox) of alkenes [O] =

no .
of oxygen provided by
Alkene -> did (compound with two
hydroxy groups (Ox)
an
oxidising agent
·
cold , dilute KMnO-oxidising agent (H) = no . of hydrogen provided by
H
HH a
reducing agent
-H
c = c +
H20 + (0) + Ho -C -
-

OH
H H it it
ethene ethane - 1 2-did ,

Reduction (Rel of
aldehydes & Ketones

Aldehyde + 10 alohol (Re)

%
Ketone >
-

2 alcohol (Rel
·
NaBHylag) or
LiAChy in dry ether
-

reducing agents
HH
# 11
H C C +
2CH) > H C OH

↓Y
-
- - -
-

H
ethanal ethanol (10 alcoholi

HH
, HOH H
11
H -

C -

C -

C -

H +
2(H] >
-
H -

C -

C -

C
-

i it it it h
%
propanone propan-2-o) (2 alcohol)

Re of carboxylic acids
carboxylic acid >
- 10 alcohol (Rel
·
NaBHylag) or
LiAChy in dry ether
-

reducing agents H HH
I o 1 I

H 4(H] - H c c OH +
Hy
-
C +
-
- -
-

OH ↓ h
ethanoic acid ethand
 Hydrolysis (Hyd) of ester
irreversible
ester ->
Carboxylic acid CHyd
heat with dilule acid//dilute alkali followed
·
by acidification
Hy
/H H H H

-I O
G +
1 Il
H
(aq) I 1

dilute acid : reversible H -

c - c o - -

H +
10 = H -

c -

C + H -

C -

C -

OH

it it
ES
IOH it i
ethylethanoate ethanoic acid ethano
acidificatn

-
&
H
dilule alkali: H

- o- - c
H S
I
Hy c
"
H
I
C
H Nam +
-

H c C
-

+ + +
- -
-
- -

on
↓ ↓ calkalitty) ↓ Nat it ↓ Oh

LESI
Esterification of alcohol//Condensation of alcohol esters have

carboxylic acid - ester CEst /1 Con1 Sweet , fruity smells

neat under reflux with
· conc .
H SO
, ,
or
HyPOp as catalyst

Combustion of alcohols
complete combustion of alcohols : alcohol + oxygen >
-
carbon dioxide + water
-

excess o

distillationsno distillation + further heat + excess Ox agents =

further
Ox of alcohols under reflux oxidise
- further ox . -to carboxylic
↑ alcohol aldehyde -
> carboxylic acids (0x) acid /

2 alcohol Ketone (8x/

130 alcohol do not undergo oxidations & Kz(r > Of is an orange oxidising agent
·
acidified K , Cr207 or acidified KMnO +
heat > for Kr Of to work as oxidising agent
-

① ② ,

S j
--
it needs It ions (which provided by acd Kz(r > Of
oxidising agents
.

potassium alcohol oxidises (ry0 + - : Orange ->

green
potassium reduce
dichromate (VI) Cr3t
mang anate Cr202-
IVIII

① KMno , oxidising agent

is a purple
> for KMnO to work as oxidising agent
-

it needs It ions (which provided by and . · KMnOy)

alcohol oxidises
Mo : purple >
-

reduce
colorless
Musi, Mn2 +
H H H O
1
H -

c -C OH + (0 - H -
i c -

10
it it ↑
ethanol (19 ethana

H H O H
III I
↓
-
-

H +
10) + H -
c -

c
-
c -

H +
Hy
↓ h it i
propan-2-ol (29
propane
 (Dehl

Dehydration of alcohols // Eli of alcohols

alcohol +
-
alkene (Deh//Eli)
alcoholigi /
hotcatalyst
vapour + of Ako powder corpieces of prmicite conc acid like conc Ho e
·

can be used as
=
catalyst

HH H

H -
1

C
-

C
-

OH >
-
&

c= ch + H 0
,

HH
it i
ethene
ethand

Alcohols with Na crystalline solid

-

while
,
alcohol + >
Na- Naalkoxide +
H219)

E E
HH

2
(H -
c
ii
-C -

2) + 2Na +
c(n #H -
-

- Na +
) + H
, (a)

ethand codium ethoxide hydrogen

Test for alcohols (Todoform test (

Tri-iodomethane //iodoform//CHI
,
forms a yellow ppt . with ketones
my
compoundsthat group

e .

g .

ethanasketones
testing step : 2 ,
NaoHag1 + heat
NaCH (9q)
R200 Nat
RCOCHy-
halogenation RCOC)y
>
-

hydrolysis
+
CHIs
Methylketone
①
-

②
codiumalt ↑ i-iodomethane

20 alcohol 20 alcohol with alkaline Is

The position of can be deduced by reacting
if the -OH is the Catom next to methyl group it will firstly get oxidised to CHzCH/OH) by the alkaline solution
>
-

on a
-

result in methyl betones

4 then iodoform-test can be tested
if no yellow ppt formed
·
= Co alcohol is not on a

H OH H carbon next to methyl

11 [O] It ~ methyl betone group .

H -
C -

C -

C -

H >
-
H -

C -

C -

C -

C
-

it h it i t it
butan-2-ol
butanone
129

Cyty-C-cla
G
O
72 NaOH 1991
step 0 : CHy CH ,
-
" -

CH
>
-
,

halogenation

CHyCHa-C
NaOH <agI
Step O : - CHyCHyCOONat +
CHIs
-

hydrolysis sodium
propanoate
 Alcohol Dissociation
alcohols haveal degree of dissociation
E > alcohol molecules do not dissociate to a great extent , when
dissolve in water

Rocag
+
ROH (aq) > =
+ H 199)

egb-lies much more alcohol molecules thanR5 and H + ions

LHS
, meaning that there are
-

H20((1 => OH 1ag) H+

+
1991

when water dissociates eab also lie LHS but there

. are more H + ions compared to dissociation of alcohols .

· alcohols are weaker acids than water

- -

Inductive effect in alcohol :

atom in the alloxide ion is bonded to an electron-donating akyl group.

Thisindusa active effect
in alonos the
oxygen
·

· this means there is more electron

density on the o'atom
·
the alkoxide ion is therefore more likely accept an A + ion and form the alcohol again
,
,

· When water dissociates the hydroxide ion

only has one other hydrogen atom
,

likely to accept an #
+
There is no extra electron density the oxygen which is less ion
·
on .

· water is stronger acid than alcohols

 more
& Ketones
Adehydes
Nucleophilic addition (NA)
aldehydes//ketones >
-

hydroxynitriles (NAI
· HCN//KCN (CN- acts as nucleophile) + heat

H32 Ao
-

I
Step 17 C
= 0
Hz) C =N
- -

nucleophilic
attack
H
j · CN-
H
reactive intermediate
etanal

-an OH
I
step z -
Hj) - I En
#y
-CEN
-

protonation H
2-hydroxypropanitrile
Coxygen reacts with agrees
H+ from HCN water or dilute acid /
,

Test for carbonyls (2 4-DNPH Test) , -

c =0 group Caldehyde , Ketone ,
- carboxylic acid ,
ester ,

2
,4-dinitrophenylhydrazine Jaka 2 4-DNPH) ,
is a
reagent which detects carbonyl compounds
amide acyl
,
halide
with [SDeCIScally
>
-

carbonyl compound undergo condensation reaction 2, 4-DAPH

aldehyde
>
deep-orange ppt. formed carbonyl present and
Ketone
-

can be
purified by recrystallization
> m
-

. p .
of formed ppt can be compared to
·
find out specific carbonyl compound

Test for
Fehling solution Tollen's reagent caka ammoniacal silver nitrate solution (
aldehyde test for aldehyde test for aldehyde
C2-oxidisinga
o ·

· contain copper (11) ions · contain Agt-oxidising agent

neat with Tollen's
heat with Fehling solution reagent
=-
aldehyde > carboxylic acid aldehyde -
Carboxylic acid
oxidise oxidise
-

(in alkaline solution

(02 + -

reduce
> Cut Agt -
> Ag carboxylic acid
reduce will become carboxylate
· clear blue -
redppt .
=
aldehyde present silver ion and form a salt)
mirror
·silver mirror =
aldehyde present
 -Carboxylic
acids

Hydrolysis (Hyl of nitrile

Mataifoudyacidvanecarboxea
nitrile >
-

carboxylic acid (Hyd) salt

· divitacid Om
a
-

result in
carboxylic acid
+ ammonium salt
acid hydrolysed
HH

10
H
1 ↑
dilite acid : H -

c -

C -
C=N + H() + 2H 0
,
H-c - -

C NHyl
↓ h OH
it
I alkali hydrolysed
dilute alkali : H-c-c

↓
-

C = N + NaOH +
120 >
-
H -c

Nat -

c -
C +
NH

H
↓ acidification

i a
H -

C -

C -

↓ H H

Acid-base reaction
in water)
·

carboxylic acids arereak acids (not completely dissociate

egb Iie LHS
.

-
CHy-c =>
↑
CHy
-y
t Ht
conc -
of H
is smaller than
CHy(OOH
#merisatio chain of molecule that is made up of many repeating
-
a
it

cmonomers
>
-
e .

g. polycethanes and
poly (chloroethanes aka PVC commonly used in making plastics
monomer monomer
Chloroethane
=

=
ethane

General formula addition polymerisation

① nat >
-

fim brace/f
f(x) (H)fn 1) n =
fit
① MHyc
=
(Hx + -

>
-

Chloroethane
poly (chloroethanes
(PVC)

·
polycalkeness are very large alkane
+ unreactive => do not undergo chem reaction
.
: non-biodegradable