4102609923604691

Maha Marathon : ORGANIC
ORGANIC CHEMISTRY
Shilpi Kaushik
NIT Jalandhar
ORGANIC CHEMISTRY
CBSE -2023
Maha Marathon : ORGANIC CHEMISTRY
Complete Theory
+
NCERT Intext Q
+
PYQs
+
Case Based Q
CBSE
Chapter Wise Weightage of chemistry CBSE Class 12

Haloalkanes & Haloarenes

Classification of Halogen Compounds

Classification based on the number of halogen atoms
Monohalogen Dihalogen Polyhalogen

Compound Compound Compound
Contain 1 halogen atom 2 halogen atoms are Contain 3 halogen atoms

attached
C2H5X CH2X CH2X
|
Monohaloalkane | CHX
CH2X |
CH2X
Dihaloalkane Trihaloalkane
Classification based on the number of halogen atoms
Monohalogen Polyhalogen
Dihalogen Compound
Compound Compound
Contain 1 halogen atom 2 halogen atoms are Contain 3 halogen

attached atoms
X X
X X
X
X
Monohaloarene Dihaloarene Trihaloarene
Monohalogen Compound
Halogen attached with Halogen attached with

sp3 Carbon sp2 Carbon
Alkyl Allylic Benzylic

Halide Halide Halide
CH3— X CH2X
Allylic carbon

Monohalogen
Compound
Halogen attached with Halogen attached with

sp3 Carbon sp2 Carbon
Monohalogen Compound
Nomenclature of Halogen Compounds
Nomenclature of alkyl halide
Common Name IUPAC Name
The common names of alkyl halides Alkyl halides are named as halo
are derived by naming the alkyl substituted hydrocarbons in the
group followed by the halide. IUPAC system of nomenclature.
Alkyl halide Haloalkane



● The dihaloalkanes having the same type of halogen atoms
are named as alkylidene halide or alkylene dihalides.
Common name: Ethylidene chloride Ethylene dichloride

(gem - dihalide) (vic-dihalide)
IUPAC Name: 1, 1-dichloroethane 1, 2-dichloroethane
Nomenclature of aryl halides
● Haloarenes are the common as well as IUPAC names of

aryl halides.
● For dihalogen derivatives, the prefixes o-, m-, p- are used
in common system but in IUPAC system, the numerals 1,2;
1,3 and 1,4 respectively are used.

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Solution
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Nature of C-X Bond

Halogen is denoted by symbol ‘X’
Nature of C-X Bond
Various features of a C-X bond

● As the size of halogens increases from fluorine to astatine, the C-X bond
length increases and bond dissociation strength decreases
Nature of C-X Bond
Various features of a C-X bond
● EN ↓ down the group, hence dipole moment which depends on the

difference in EN of C and halogen also ↓ down the group.
● The only exception in group 17 is that the dipole moment of the C-Cl
bond is more than C-F, everything else follows the normal trend.
Nature of C-X Bond
Dipole
Bond C-X Bond
Bond moment/Deby
length/pm enthalpies/kJmol−1
e
CH3−F 139 452 1,847
CH3−Cl 178 351 1,860
CH3−Br 193 293 1,830
CH3−I 214 234 1,636
Preparation of Haloalkanes
❏ From Alcohols:
❏ From Alcohols:
● Reactivity order of halogen acids : HI > HBr > HCl

● ZnCl2 is required with 1o and 2o alcohols but not with 3o alcohols.
❏ From Alcohols:
❏ From Alkenes:
From Alkenes
Peroxide Absent Peroxide Present
2-Bromopropane 1-Bromopropane
Mark. Anti Mark.
Addition Addition
❏ Addition of halogens:
● Addition of Br2 in CCl4 to an alkene resulting in discharge of

reddish brown colour of Br2 constitutes an important method
for the detection of double bond in a molecule.
❏ Free Radical Halogenation of Alkanes
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Solution
❏ Finkelstein Reaction: Alkyl Iodides are generally prepared

by this method
❏ Swarts Reaction: Alkyl Fluorides are generally prepared

by this method.
Preparation of Haloarenes
❏ From hydrocarbons by electrophilic substitution
● The ortho and para isomers can be easily separated due to

large difference in their melting points.
● Reactions with iodine are reversible in nature and required
the presence of an oxidising agent (HNO3, HIO4)
● Fluoro compounds are not prepared by this method due to
high reactivity of fluorine.
Preparation of Haloarenes
❏ From amines by Sandmeyer’s reaction
Replacement of the diazonium group by iodine does not

require the presence of cuprous halide and is done simply
by shaking the diazonium salt with potassium iodide.
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Solution
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Physical Properties
Physical properties of any compound depend largely on
It’s mass The type of intermolecular

and intramolecular forces of
attraction
❏ Colour & Physical state:

❏ Boiling Point:
● Boiling points of Chlorides, Bromides and Iodides are considerably

higher than those of the hydrocarbons of comparable molecular
mass.
● For isomeric Haloalkanes :

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❏ Boiling Point:
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❏ Density:
● The density of Halogen containing Compounds increases
with increase in number of C-atoms, X-atoms and atomic
mass of the X-atoms
❏ Solubility
● The haloalkanes are very slightly soluble in water.
● However, haloalkanes tend to dissolve in organic solvents

because the new intermolecular attractions between
haloalkanes and solvent molecules have much the same
strength as the ones being broken in the separate
haloalkane and solvent molecules.
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1. Reaction with Metals
Preparation of Grignard Reagent (RMgX)
In the Grignard reagent, the carbon-magnesium bond is covalent but

highly polar, with carbon pulling electrons from electropositive
magnesium; the magnesium halogen bond is essentially ionic.
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𝛿− 𝛿+ 𝛿−
R - Mg X
● Grignard reagents are highly reactive and react with any source of
proton to give hydrocarbons. Even water, alcohols, amines are
sufficiently acidic to convert them to corresponding hydrocarbons.
RMgX + H2O RH + Mg(OH)X
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Wurtz Reaction
● Alkyl halides on treatment with Sodium metal in dry ether

(free from moisture) solution give higher Alkanes.
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Wurtz Reaction
● Number of C-atoms in alkane is twice of the number of

C-atoms in Alkyl Halide.
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Wurtz Reaction
● Holds good for the formation of Alkane with even number
of C atoms.
● Not preferred for the formation of Alkane with odd number

of C atoms.
Example :
● Mixture of alkanes is formed.

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2. Nucleophilic Substitution Reactions

In this reaction, a nucleophile reacts with a haloalkane and a
substitution reaction takes place and halogen atom (leaving group)
departs as halide ion.
Nucleophilic Substitution Reaction
SN2 Reaction SN1 Reaction

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Retention, Inversion and Racemisation

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Ambident Nucleophile
● Nucleophiles that possess two nucleophilic centres and
are called ambident nucleophiles
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Solution
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Mechanism of SN2 Reaction

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● As the reaction progresses and the bond between the incoming Nu and the
‘C’ atom start forming, the bond between carbon atom and LG weakens.
● The attack only takes place from the backside of the Leaving Group.
● In case of halides, Iodide ion is a better leaving group than Fluoride ion.
● Polar aprotic solvent generally favour SN2 reactions such as

acetone,DMSO etc.
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Title
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Substitution Nucleophilic Unimolecular (SN1)
● Follows 1st order Kinetics

● Rate of reaction only depends upon substrate i.e
Haloalkanes
Rate of reaction ∝ [Substrate]
● This reaction is carried out in polar protic solvents
such as water, alcohol, acetic acid etc.
● Reaction follows 2 step mechanism.
● Formation of Transition state is the slowest step or
rate determining step.
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Substitution Nucleophilic Unimolecular (SN1)
● Order of reactivity of alkyl halide :

1° Alkyl halide < 2° Alkyl halide < 3° Alkyl halide
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Comparing SN1 and SN2 Reaction

Related Concepts SN1 Reaction SN2 Reaction
Rate law Unimolecular Bimolecular
Haloalkane 3o > 2o > 1o 3o < 2o < 1o

reactivity
Solvent Polar solvent Polar aprotic

(protic solvent) solvent
Stereochemistry Racemic mixture Inversion
Nucleophile Weak Strong

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Solution
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Solution
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3. Elimination Reaction
Introduction
● It involves removal of the two groups, generally one being a
proton and other being leaving group to form an unsaturated
compound.
● Leaving group X⊝ = I⊝, Br⊝, Cl⊝, ⊝OTs etc.
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Elimination Reaction
Introduction
● The removal usually takes place due to the action of acids and bases
or action of metals.
● It can also happen through the process of heating at high
temperatures.
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β-elimination:
● When haloalkane with β-hydrogen atom is heated with
ethanolic potassium hydroxide, there is elimination of hydrogen
atom from β-carbon atom and a halogen atom from 𝛼-carbon
atom. As a result, an alkene is formed.
● Since β-hydrogen atom is involved in elimination, it is often
called β-elimination reaction.
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For Example:
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Saytzeff Rule
If there is possibility of formation of more than one alkene due

to the availability of more than one β-hydrogen atoms, usually
one alkene is formed as the major product.
According to this rule in dehydrohalogenation reactions, the
preferred product is that alkene which has the greater number
of alkyl groups attached to the double bonded carbon atoms.
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Saytzeff Rule
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Elimination Vs Substitution
● An alkyl halide with β-hydrogen atoms when reacted with a
base or a nucleophile has two competing routes
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Which route will be taken up depends upon
Nature of alkyl Strength and Reaction conditions

halide size of
base/nucleophile
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● A bulkier Nucleophile will prefer to act as a base and

abstracts a proton rather than approach a tetravalent ‘C’
atom (steric reasons) and vice versa.
● A primary alkyl halide will prefer a SN2 reaction, a

secondary halide- SN2 or elimination depending upon the
strength of base/nucleophile.
● A tertiary halide- SN1 or elimination depending upon the

stability of carbocation or the more substituted alkene.
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Reactions of Haloarenes
Reactions of Haloarenes
Nucleophilic Electrophilic Reactions with

Nu Substitution Substitution Metals
Replacement of Halogenation Wurtz-Fittig

halogen by -OH Reaction
Nitration Fittig
Group
Sulphonation Reaction
Friedel Craft Alkylation

Friedel Craft Acylation
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1. Aromatic Nucleophilic Substitution
● Haloarenes are extremely less reactive towards Nucleophilic

substitution because:
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Aromatic Nucleophilic Substitution
● Haloarenes are extremely less reactive towards

Nucleophilic substitution because:
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● Haloarenes are extremely less reactive towards

Nucleophilic substitution because:
3. Instability of Phenyl Cation
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4. Repulsion
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Replacement of Halogen by hydroxyl group
❏ Dow’s Process
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In the presence of e- withdrawing group (NO2)
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In the presence of e- withdrawing group (NO2)
● The presence of an electron withdrawing group (-NO2 ) at

ortho- and para-positions increases the reactivity of
haloarenes.However,no effect is observed in reactivity when
electron withdrawing group is at meta position.
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2. Electrophilic Substitution Reactions of Haloarenes
Electrophilic aromatic substitution : Reaction in which an

atom that is attached to an aromatic system (usually
hydrogen) is replaced by an electrophile.
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Electrophilic Substitution Reactions of Haloarenes
● Due to resonance, the electron density increases more at

ortho-and para-positions than at meta-positions(o.p directing)
● Further, the halogen atom because of its -I effect has some
tendency to withdraw electrons from the benzene ring.
● As a result, the ring gets somewhat deactivated as compared to
benzene and hence the electrophilic substitution reactions in
haloarenes occur slowly and require more drastic conditions as
compared to those in benzene.
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Electrophilic Substitution Reactions of Haloarenes
● Haloarenes undergo the usual electrophilic reactions of

the benzene ring such as :
Halogenation
Nitration
Sulphonation
Friedel - Crafts reactions

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Halogenation Reaction
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Nitration Reaction
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Sulphonation Reaction
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Friedel Craft Alkylation

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Friedel Craft Acylation

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Reaction with metals

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Dichloromethane (Methylene chloride)
1. Solvent as a paint remover, 1) Harms the human central

propellant in aerosols nervous system
2. Solvent in the manufacture of 2) Can lead to slightly impaired
drugs hearing and vision.
3. Metal cleaning and finishing 3) Direct contact with the eyes
solvent can burn the cornea.
USE Drawback
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Trichloromethane (Chloroform)
1. Today - production of the freon 1) Depresses the central nervous

refrigerant R-22. system
2. Once used- general anaesthetic 2) Breathing short time - dizziness,
in surgery (replaced by-Ether) fatigue, and headache.
3. Metal cleaning and finishing 3) damage to the liver( CCl4 to
solvent Phosgene.
USE Drawback
Oxidised by air in the presence of light to an extremely poisonous gas - phosgene.

Stored in closed dark coloured bottles completely filled so that air is kept out.
USE
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Triiodomethane (Iodoform)
It was used earlier as an antiseptic but the antiseptic properties are due to the
liberation of free iodine and not due to iodoform itself
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Tetrachloromethane (Carbon tetrachloride)
● Use in the manufacture of refrigerants and propellants for aerosol cans and
feedstock
● mid 1960s - widely used as a cleaning fluid, both in industry, as a degreasing
agent, and in the home, as a spot remover and as fire extinguisher.
● Liver cancer in humans

● Permanent damage to nerve cells
● Depletes the ozone layer
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Freons
● Extremely stable, unreactive, non-toxic, non-corrosive and easily liquefiable gases

● Produced for aerosol propellants, refrigeration and air conditioning purposes
● In stratosphere, freon is able to initiate radical chain reactions that can upset the
natural ozone balance
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p,p’-Dichlorodiphenyltrichloroethane(DDT)
1. first chlorinated organic 1) insects developed resistance to DDT

insecticides 2) DDT is not metabolised very rapidly by
2. World War II - against the animals; instead, it is deposited and
mosquito that spreads malaria stored in the fatty tissues
USE Drawback
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PYQs-Haloalkanes and Haloarenes

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Solution:
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Solution:
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Solution:
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Solution:
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Solution:
Alcohols, Phenols, Ethers

Classification of Alcohol
Primary Alcohols: Hydroxyl group is attached to primary (1o) carbon atom.
R–CH2–OH
Secondary Alcohols: Hydroxyl group is attached to secondary (2o) carbon atom.
Isopropyl alcohol
Tertiary Alcohols: Hydroxyl group is attached with tertiary (3o) carbon atom.
Nomenclature of Alcohol
Common Name: Write alkyl group and adding the word alcohol in it
Example:
IUPAC: Substituting ‘e’ of alkane with the suffix ‘ol’
Example:
Physical Properties of Alcohol
● Alcohols are colourless liquids with specific smell. They are

soluble in water due to H-bonding. These are partially soluble
in organic solvents.
● They are liquid in nature up to 12-carbon.
● Boiling point ∝ molecular mass
● Boiling point of alcohols are higher than equivalent ethers. It is

due to intermolecular H-bonding.
Preparation of alcohol
From Alkenes
(i) By acid catalysed hydration
From Alkenes
● Mechanism
Step 1: Protonation of alkene to form carbocation by electrophilic

attack of H3O+
Step 2: Nucleophilic attack of water on carbocation

From Alkenes
● Mechanism
Step 3 : Deprotonation to form an alcohol.

From Alkenes
(ii) Oxymercuration-Demercuration
Addition-accordance with Markovnikov's rule without any

rearrangement
From Alkenes
(iii) Hydroboration - Oxidation of alkenes
❖ From Alkyl halide

From Reactions involving Grignard reagent
❖ Reaction with methanal
In this reaction, methanal gives primary alcohol, while any other

aldehyde gives secondary alcohol.
❖ Reaction with other aldehyde
❖ Reaction with ketone
In this reaction, ketones form tertiary alcohols.

❖ From Carbonyl Compounds
● By reduction of aldehydes and ketones

○ Aldehyde gives primary alcohols and ketone gives
secondary alcohols
Catalyst used for reduction - (1) finally divided Ni, Pt and Pd
(2) NaBH4 - it reduces only carbonyl group and has no effect on

other reducing group.
(3) LiAlH4 it is a strong, unselective reducing agent it will reduce

aldehydes, ketones, esters, carboxylic acid chlorides, carboxylic
acids and even carboxylate salts to alcohols.
LiAlH4 is an expensive reagent. Commercially, acids are reduced

to alcohols by converting them to the esters followed by their
reduction using hydrogen in the presence of catalyst
Preparations of Diols:- (Cold , dil alkaline KMnO4 , Baeyer’s Reagent)
From Alkenes
Preparations of Diols:- (Cold , dil alkaline KMnO4 , Baeyer’s Reagent)
From Alkenes
Mechanism (Syn addition)

Preparations of Diols:- (OsO4, H2O2)
From Alkenes
Syn addition
Preparations of Diols:- (Peroxy Acid/H3O+)
From Alkenes
Anti addition
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Solution
Dehydration reaction
● Dehydration means removal of a molecule of water
● Formation of either alkenes or ethers.
● Dehydration can be carried out either with protonic acid such
as H2SO4, Al2O3 , P2O5.
● Primary alcohols when heated with conc. H2SO4 at 433 - 443 K,
they undergo intramolecular dehydration to form alkenes.

Secondary and tertiary alcohols undergo dehydration under milder

condition
Ease of dehydration of alcohols follows the order -

3o alcohol > 2o alcohol > 1o alcohol
Substitution reaction
In substitution reaction of alcohol, OH group of alcohol is replaced by

halogen of acid either by SN2 or SN1 reaction
1. Reaction with halogen acids
● Mechanism
● Primary alcohols - react by SN2 mechanism while secondary

and tertiary alcohol react by SN1 mechanism
● Order of reactivity of the halogen acids:

➢ HI > HBr > HCl
● Reactivity of alcohols:
● Tertiary > Secondary > Primary

2. Reaction with PCl3
● Primary and secondary alcohol, not work with tertiary alcohols
● Mechanism SN2 :
No carbocation rearrangement

4. Reaction with SOCl2 with pyridine

● It is the best reagent because the product (gaseous SO2 and
HCl) leave the reaction mixture.
● Mechanism SN2
Step -1
Oxidation of alcohol
Oxidation of alcohols involves the formation of a carbon oxygen

double bond with cleavage of an O-H and C-H bonds.
Bond Breaking
Note - Oxidation of alcohols depend upon oxidising agents

Alkaline KMnO4 Strong oxidising agent
Primary alcohol is oxidised to an aldehyde and then to an acid both

containing the same number of carbon atoms.
CH3CH2OH [O] CH3CHO [O] CH3COOH

Ethyl alcohol Acetaldehyde Acetic acid
(2C-atoms) (2C-atoms) (2C-atoms)
A secondary alcohol when oxidised gives a ketone.
A tertiary alcohol not oxidised by alkaline KMnO4

Acidic K2Cr2O7 Strong oxidising agent
Primary alcohol is easily, oxidised to an aldehyde and then to an acid
CH3CH2OH CH3CHO CH3COOH

[O] [O]
Ethyl alcohol Acetaldehyde Acetic acid
(2C-atoms) (2C-atoms) (2C-atoms)
A secondary alcohol when oxidised gives a ketone
A tertiary alcohol not oxidised by acidic K2Cr2O7

Jones reagent
● Jones reagent consists of chromium trioxide and sulfuric acid

dissolved in a mixture of acetone and water.
● Oxidation of primary and secondary alcohols to carboxylic

acids and ketones
CrO3 O
aq. H2SO4
R1 OH acetone
R1 OH
OH O
CrO3
aq. H2SO4
R1 R2 acetone
R1 R2
Introduction to Phenol
● In Phenols, the OH group is attached to sp2 hybridised carbon

of an aromatic ring.
● The carbon oxygen bond length in phenol is slightly less than
that in methanol. This is due to
○ partial double bond character because of the
conjugation of unshared electron pair of oxygen with the
aromatic ring
○ sp2 hybridised state of carbon to which oxygen with
attached.
Acidity of Phenol
Reaction which show acidic character of phenol
1. Reaction with metal (Na)
2. Reaction with sodium hydroxide

Acidity of Phenol
Resonance in phenol
● In phenol the sp2 hybridised carbon of benzene ring which acts

as an electron withdrawing group.
● In resonance structure of phenol, oxygen of -OH group will be

positive
Acidity of Phenol
Resonance in phenoxide ion
Phenoxide ion more stable due to resonance.

Acidity of Phenol
Acidic nature of Substituted Phenol
Electron Withdrawing group - (-NO2, -COOH, -CN)
● Enhances the acidic strength of phenol.
● This effect is more pronounced when such a group is present at

ortho and para positions.
Electron donating group - (-OH, -OR, -NH2)
● Decreases the acidic strength of phenol.

Preparation of Phenol
Dow’s Process
Mechanism through Benzyne intermediate

Cumene Process
● Cumene (isopropylbenzene) is oxidised in the presence of air

to cumene hydroperoxide which is converted to phenol and
acetone by treating with dilute acid
From diazonium salts
● A diazonium salt is formed by treating an aromatic primary

amine with nitrous acid (NaNO2 + HCl) at 273-278 K
● When benzene diazonium chloride solution is warmed with

warm water or dilute acids , phenol is formed with evolution of
nitrogen.
Reaction of phenol
1. Esterification
● Phenols react with carboxylic acids, acid chlorides and acid

anhydrides to form esters.
● The reaction with carboxylic acid and acid anhydride is carried

out in the presence of a small amount of concentrated
sulphuric acid.
● The reaction is reversible, and therefore, water is removed as

soon as it is formed.
Example
Reaction of phenol
● The reaction with acid chloride is carried out in the presence

of a base (pyridine) so as to neutralise HCl which is formed
during the reaction and shifts the equilibrium to the right
hand side.
Reaction of phenol
1. Esterification
The introduction of acetyl (CH3CO) group in alcohols or phenols is

known as acetylation
Reaction of phenol
Phenol reacts with PCl5 to give triphenyl phosphate as a major

product.
Reaction of phenol
3. Reaction with zinc
Phenol is converted to benzene on heating with zinc dust

Electrophilic Aromatic Substitution
Bromination
● The - OH group is ortho and para directing.
● Phenol activates the benzene nucleus towards

electrophilic substitution reactions at ortho and
para-positions.
● When the reaction is carried out in solvents of low polarity

such as CHCl3 or CS2 and at low temperature, monobromo
phenols are formed
Br2 in CS2
273 K
Minor
Major
Reaction of benzene ring
Nitration
● Phenol activates the benzene nucleus towards electrophilic

substitution reactions at ortho and para-positions.
● With dilute nitric acid at low temperature (298 K), yields a

mixture of ortho and para nitrophenols.
Dilute HNO3
o-Nitrophenol
p-Nitrophenol
Nitration
Ortho and para isomer can be separated by steam distillation
Nitration of phenol
O - Nitrophenol P - Nitrophenol
Intramolecular H - bonding Intermolecular H - bonding
less volatile
Steam volatile High boiling point
Low boiling point
Nitration
● Reaction with concentrated nitric acid.
● Phenol is converted to 2,4,6-trinitrophenol (picric acid)

Kolbe’s Reaction
Kolbe reaction
● Reaction of sodium phenoxide with carbon dioxide (weak

electrophile)
● At 130-140°C under pressure of (4-7) atmospheres followed by

acid hydrolysis, salicylic acid (o-Hydroxybenzoic acid) is
formed.
Reimer - Tiemann Reaction
Reimer - Tiemann reaction
● Reaction of phenol with chloroform in the presence of sodium

hydroxide.
● A –CHO group is introduced at ortho position of benzene ring.

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Solution
Introduction of ether
Organic compound having R—O—R' as functional group are called ethers.
Classification of Ethers
Simple or Symmetrical Mixed or Unsymmetrical
Alkyl or aryl groups attached to the Alkyl or aryl groups attached to the
oxygen atom are the same. oxygen atom are different.
C6H5 - O - CH3
CH3 - O -CH3
C2H5 - O - C2H5 CH3 - O - C2H5

Introduction of ether
Bond angle is slightly greater than the tetrahedral
angle due to repulsive interaction between two bulky
alkyl groups.
Alkanes and ethers of comparable molecular mass have similar

boiling point due to weak polarity of ether bonds.
Formulae CH3(CH2)3 CH3 C2H5OC2H5 CH3(CH2)3OH
Name n - pentane Ethoxyethane Butan - 1 - ol
B.P./K 309.1 307.6 390
The large difference in boiling points of alcohols and ethers is due to

the presence of hydrogen bonding in alcohols.
Preparation of ether
Dehydration of alcohol
Williamson synthesis
Williamson synthesis
● Alkyl halide should be primary and aIkoxide should be

secondary or tertiary.
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Solution
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Solution
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PYQ- ALCOHOLS
PHENOLS AND ETHERS
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Solution:
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Solution:
ALDEHYDES, KETONES AND

CARBOXYLIC ACIDS
Aldehydes and Ketones
In aldehydes, the carbonyl group is bonded to a carbon and

hydrogen while in the ketones, it is bonded to two carbon
atoms
Nomenclature and Structure of Carbonyl Group
Common names ;
IUPAC names ;
IUPAC names ;
Preparation of aldehyde & ketone

Etard reaction
Use of chromic oxide

Gatterman – Koch reaction

From nitriles
Ozonolysis of alkene
Oxidation of alkane & alkene
From Alkenes :
Reagents : alkaline / acidic KMnO4 and acidic K2Cr2O7

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Solution
Physical Properties
Boiling Point
The boiling points of aldehydes and ketones are higher than
hydrocarbons and ethers of comparable molecular masses. It is due to
weak molecular association in aldehydes and ketones arising out of the
dipole-dipole interactions. Also, their boiling points are lower than those
of alcohols of similar molecular masses due to absence of intermolecular
hydrogen bonding
Physical Properties
Solubility
The solubility of aldehydes and ketones decreases rapidly
on increasing the length of alkyl chain. All aldehydes and ketones are
fairly soluble in organic solvents like benzene, ether, methanol,
chloroform,
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Solution
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Reactions of aldehyde and ketone


Reduction reaction
Oxidation reaction
Tollen’s, Fehling and Benedict reagent
Tollen’s reagent
AgNO3 + 2NH4OH [Ag(NH3)2]+ + NO3- + 2H2O
Tollen’s reagent is selective, it does not attack olefinic bond.
Fehling’s reagent
Fehling’s Solution A : CuSO4.5H2O (Blue vitriol)

Fehling’s Solution B : Rochelle's salt (Sodium Potassium Tartrate)
𝞪 Substitution Reaction
Haloform
Alternative reagent : NaOX
★ Necessary condition for Haloform reaction is

presence of 3 ∝–H’s adjacent to carbonyl carbon
Aldol condensation
● Condition : Aldehydes and Ketones containing ∝–H’s
shows this reaction.
● Reagents used are : 10% NaOH, KOH, Ba(OH)2, K2CO3
etc.
Aldol condensation
Mechanism of Aldol Condensation
Step-1:In reverse order, The hydroxide ion deprotonates the
aldehyde.
Step-2:Here Enolate ion 1 adds to the unreacted aldehyde.

Aldol condensation
Step-3: Alkoxide ion 2 is protonated by water.
Step-4:A small amount of aldol is converted into enolate ion (4) by hydroxide
ion.
Aldol condensation
Step-5: Here Enolate Ion(4) loses a hydroxide ion.
Aldol condensation
Cross Aldol Condensation :
● On using two types of carbonyl compounds both having α-hydrogen
atoms we get a mixture of four condensed product.
Cannizzaro’s reaction
● Condition : It is the Characteristic reaction of a Carbonyl

compound which do not contain α–H.
● Reagent used : Conc. NaOH/ KOH OR 50% NaOH / KOH
Mechanism
Step 1
A nucleophile such as a hydroxide ion is used to attack the carbonyl group of the giv
aldehyde, causing a disproportionation reaction and giving rise to an anion carrying 2
negative charges.
Mechanism
Step 2
This resulting intermediate can now function as a hydride reducing agent. Due to its
unstable nature, the intermediate releases a hydride anion. This hydride anion
proceeds to attack another aldehyde molecule. Now, the doubly charged anion is
converted into a carboxylate anion and the aldehyde is converted into an alkoxide
anion.
Mechanism
Step 3
In this final step, water offers a proton to the alkoxide anion which gives rise to the
final alcohol product. The reaction can proceed since the alkoxide is more basic than
water. Now, the carboxylate ion gives rise to the final carboxylic acid product when
acid workup is used
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Solution
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Solution
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Solution
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Solution
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Solution
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Solution
Carboxylic acid
Preparation of carboxylic acid
Preparation of carboxylic acid

Preparation of Benzoic acid
Physical Properties
Boiling Point
Carboxylic acids are higher boiling liquids than aldehydes, ketones
and even alcohols of comparable molecular masses. This is due to
more extensive association of carboxylic acid molecules through
intermolecular hydrogen bonding. The hydrogen bonds are not
broken completely even in the vapour phase. In fact, most carboxylic
acids exist as dimer in the vapour phase or in the aprotic solvents.
Physical
Physical
Properties
Properties
of Carboxylic acid
Solubility
Aliphatic carboxylic acids having up to four carbon atoms are miscible in
water due to the formation of hydrogen bonds with water. The solubility
decreases with increasing number of carbon atoms
Reactions of carboxylic acid
Reduction reaction :
To Alkanes : Red P + HI
To Alcohols : (a) LiAlH4 , (b) B2H6 (selective)
Reduces –COOH group but does not affect other functional groups such
as ester, nitro, halo group etc

Decarboxylation reaction :
Decarboxylation reaction : Kolbe’s Electrolysis

An aqueous solution of sodium or potassium salts of carboxylic acids on
electrolysis gives alkane containing even no. of carbon atoms at anode.
Conversion to carboxylic acid derivative :
Conversion to carboxylic acid derivative :
Dehydrating agents: conc. H2SO4 or P4O10 / Δ

Esterification :
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PYQs-Aldehydes, Ketones and

Carboxylic Acids
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Solution:
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Solution:
Case Study
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Solution:
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Solution:
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Solution:
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Solution:
Amines
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Amines
Introduction
AMINES
Amines are derivatives of ammonia in which one
or more hydrogen atoms are replaced by alkyl
group(s).
Classification of Amines
Examples of Amines
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Structure of
amines
Structure of Amines
Pyramidal shape of trimethylamine

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Classiﬁcation
Classiﬁcation
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Preparation of
amines
Preparation of Amines
Reduction of Nitro Compounds
Nitrobenzene Aniline
Nitrobenzene Aniline
Hoffmann Ammonolysis of Alkyl Halides
This process of cleavage of the C–X bond by ammonia molecule is known

as ammonolysis.
❏ Mixture is
obtained
❏ 1o amine is obtained as a major product by
taking large excess of ammonia.
Reduction of Nitriles
H2/Ni Or LiAlH4
CH3-C≡N CH3CH2-NH2
Na/C2H5OH
Acetonitrile Ethylamine
Red with Na/C2H5OH is called

Mendius Reduction
Reduction of Amides
Amide Amine
Gabriel Phthalimide Synthesis

Hoffmann Bromamide Degradation

“To prepare 1° Amines”
Amide
1° Amine Sodium Carbonate Sodium Bromide

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Solution
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Solution
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Solution
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Physical
properties
Physical Properties
(a) H-bonding
❖ H-bonding (weaker as compared to H-O-H)
1o Amine 2o Amine
❖ In 3o amine (due to absence of H-atom) H-bonding is

not possible
Physical Properties
(b) Boiling Point
❖ Order of B.P:
1o amine > 2o amine > 3o amine
❖ Order of volatility:
Physical Properties
(c) Solubility
❖ Low molecular weight amines are soluble in
water.
❖ The water solubility of amines decreases with
increasing size of alkyl group.
Physical Properties
(c) Solubility
1o Amine 2o Amine 3o Amine
❖ Order of Solubility:
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Chemical
reactions of
amines
Chemical Reactions of Amines
Basic Character of Amines

Basic Character of Amines
In Terms of Kb & pKb values
Larger Kb value Smaller pKb value
Stronger Base
Order of Basic Strength
In Gaseous Phase
BASIC +I
STRENGTH ∝ Effect
In Aqueous Medium
∴ Experimentally determined order of basicity is
R ⇒ CH3 : 2° > 1° > 3° > NH3
R ⇒ C2H5 : 2° > 3° > 1° > NH3

“Aromatic Amine are less basic than

Aliphatic Amine”
“∵ Due to Resonance Lone Pair is

not easily available for protonation”
Acylation “Given by 1° & 2° Amines”
Ethanamine N-Ethylethanamide
(1° Amine)
Acylation
N-Ethylethanamine N,N-Diethylethanamide
(2° Amine)
Carbylamine Reaction:
“Given by 1o Aliphatic & Aromatic Amines”
Reaction with Nitrous Acid:
“For Aliphatic Amines”
Reaction with Nitrous Acid:

“For 1° Aromatic Amines”
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Heisenberg’s
test for
amines
To distinguish 1°, 2° & 3° Amines

Benzene Sulphonyl
chloride
1° R-NH2 2° R2-NH 3° R3-N
R R
R
N-Alkyl benzene
N,N-Dialkyl benzene
sulphonamide sulphonamide
Soluble in NaOH Insoluble in NaOH
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Electrophilic
substitution
reaction of Aniline
Bromination
Bromination
“ To form para product”

Nitration
Nitration
“ To form para product”

Sulphonation
Friedel Crafts Rxn
“Due to salt
formation
N becomes highly
deactivating”
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DIAZONIUM
SALTS
DIAZONIUM SALTS
N2+ group is called diazonium group

Method of Preparation of Diazoniun Salts
The conversion of primary aromatic amines into

diazonium salts is known as diazotisation.
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Chemical
Reactions
Friedel Crafts Rxn
Reactions involving displacement of nitrogen

Chemical Reactions
Reactions involving retention of diazo group coupling reactions

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Solution
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Solution
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PYQs-Amines
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Solution:
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Solution:
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Solution:
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Solution:
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Biomolecules
Biomolecules
Introduction to biomolecules
Biomolecules: A biomolecule is a chemical

compound found in living
organisms. These include chemicals
that are composed of mainly carbon,
hydrogen, oxygen, nitrogen, sulfur
and phosphorus. Biomolecules are
the building blocks of life and
perform important functions in
living organisms
Introduction to biomolecules
● Carbohydrates
The polyhydroxy carbonyl compounds are called
carbohydrates.
Biomolecules
● Classification of Carbohydrates
1. Based on number of units :
● Monosaccharides : Simplest units which cannot be simplified

further.
○ Example : Glucose , Manose , Fructose etc.
● Oligosaccharides : 2 to 10 units of monosaccharides.
○ Example of 2 units : Sucrose , Maltose , Lactose
● Polysaccharides : Greater than 10 units of monosaccharides

(very high units : sometimes 1000)
○ Example : Starch , cellulose etc
Classification of biomolecules
2. Based on water solubility :
Carbohydrates
Sugar Non-sugar
● Crystalline ● Non - Crystalline

● Water soluble ● Water insoluble
● Sweet in taste ● Tasteless
● Ex : Glucose , fructose , ● Ex : Starch ,
sucrose cellulose
Classification of biomolecules
3. Based on reducing property
Carbohydrates
Reducing Sugar Non-reducing sugar
● Those which can reduce ● Those which cannot
Tollen’s reagent and fehling’s reduce tollen’s reagent
reagent. and fehling’s reagent.
● Ex : glucose , fructose , lactose ● Ex : Starch , cellulose ,
, maltose Sucrose
● Tollen’s reagent and fehling’s reagent are mild oxidising agents.

Monosaccharides
Those simple carbohydrates which cannot be further simplified.
Monosaccharides
Aldoses Ketoses
● Monosaccharide that ● Monosaccharide that

contains an aldehyde group contains an group
(-CHO) and rest other -OH and rest other -OH
group group
Aldoses
● General representation : n ⟶ 1 to 7
Ketose
● General representation : n ⟶ 0 to 6
D/L configuration (relative configuration)
● Assigned for carbohydrates and amino acids only.
● Standard compound ⟶ Glyceraldehyde

D/L configuration (relative configuration)

Glucose
D- L-
Cyclic hemiacetal structure of glucose

Anomers
These carbohydrates which differ in configuration only at anomeric carbons

are known as anomers.
Epimers
These carbohydrates which differ in configuration only at one

carbon other than anomeric carbon are known as epimers.
Another examples for epimers

Haworth Structure of glucose

Haworth Structure of glucose

● Hemicyclic structure of glucose is present when
glucose is present in solid state.
● Free -CHO group is formed when a reagent
breaks the cyclic (hemicatela) structure is
broken into an open chain glucose structure.
● Weak reagent cannot break the cyclic
hemiacetal structure.
Mutarotation
The spontaneous change in the specific rotation value of an optically active
compound is known as mutarotation.
Fructose
● Structural formula
● Number of chiral centre = 3

● Number of stereoisomers = 23 = 8
● Number of stereoisomers for glucose
= 24 = 16
Fructose
● Stereochemical
formula
Fructose
● Stereochemical
formula
3-D , 4-L , 5-L

1,3,4,5,6-pentahydroxyhexan-2-one
L (+) Fructose
Cyclic hemiacetyl structure of fructose

Haworth structure of fructose
Inspired by furane , he made fructofuranose.
𝛂 - D ⊖ fructose
Cyclic hemiacetyl structure of fructose
Haworth structure of fructose
Inspired by furane , he made fructofuranose.
𝛂 - D ⊖ fructose
Sucrose
Sucrose, commonly known as “table sugar” or “cane sugar”, is a carbohydrate

formed from the combination of glucose and fructose.
Structure of Sucrose
Maltose (Malt sugar)
Maltose is a sweet disaccharide carbohydrate consisting of two

glucose units.
Structure of maltose
Maltose is a very rich source of glucose.
It is a reducing sugar.
Lactose
Lactose is a large sugar molecule that is made up of two

smaller sugar molecules, glucose and galactose.
Structure of lactose
It is also a reducing sugar.

Structure of lactose
● If main functional C are engaged in glycosidic linkage , and are

not free at any unit , then the sugar will be non-reducing.
● And if atleast one functional C is free, and not involved in
glycosidic linkage , then sugar will be reducing sugar.
Starch
It is the mixture of two polysaccharides
Amylose (15-20 %) Amylopectin (80-85 %)

Amylose
● Linear polymer of 𝛂-D⊕ glucose unit (100 -1000)
● (1, 4) 𝛂 glycosidic linkage
● Water soluble
Structure of Amylose
(1, 4) 𝛂 glycosidic linkage

Amylopectin
● Cross Linked polymer of 𝛂-D⊕ glucose
● (1, 4) 𝛂 glycosidic linkage, (1, 6) cross link
● Water insoluble
Structure of Amylopectin
(1, 6) glycosidic linkage (cross link)
(1, 4) 𝛂 glycosidic linkage

Cellulose
● It is a linear polymer of 𝛃 - ⊕ glucose.
● It has (1, 4) 𝛃 glycosidic linkage

Structure of Cellulose
Carbohydrates Reducing sugar Shows mutarotation
Glucose ✔ ✔
Fructose ✔ ✔
Mannose ✔ ✔
Sucrose ❌ ❌
Maltose ✔ ✔
Lactose ✔ ✔
Starch ❌ ❌
Cellulose ❌ ❌
Reaction of carbohydrate with Br2

Example
Reaction of carbohydrate with HNO3

● Example
Reaction of carbohydrate with HI

Reaction of carbohydrate with NH2OH

Reaction of carbohydrate with HCN

Reaction of carbohydrate with Ac2O

Osazone formation
Used for characterisation of sugars in carbohydrates

Glucose
glucosazone
Fructose
Osazone of fructose
Osazone formation
● Glucose and fructose have same C-3 , C-4 , C-5 configuration.

● Hence osazone of fructose is identical to glucosazone.
Amino acids
𝞪-Amino acids
If in a correct fischer formula , -NH2 is on right side , then it is D configuration and

if it is on left side , it is L configuration.
Amino acids
Amino acids are the building blocks for protein synthesis.

Types of amino acids
Neutral 𝞪-amino Acidic 𝞪-amino

Basic 𝞪-amino acids
acids acids
One -NH2 group and One -NH2 group and Two -NH2 group and
one -COOH group two -COOH group one -COOH group
Example :
S.N Neutral amino acids Name Symbol
1 Glycine gly
2 Alanine Ala
3 Valine Val
4 Leucine Leu
5 Phenylalanine Phe
Neutral 𝞪-amino acids
General formula :
Example :
S.N Neutral amino acids Name Symbol
1 Glycine gly
2 Alanine Ala
3 Valine Val
4 Leucine Leu
5 Phenylalanine Phe
General formula :
Example :
n Basic amino acids Name Symbol
n=3 Arginine Arg
n=4 Lysine Lys
Arginine is the strongest basic amino acid due to guanine group.

Zwitter ion
Isoelectric point (pI)
It is equal to the pH at which maximum concentration of amino acid remains in

the form of zwitter ion.
Characteristics
1. In zwitterionic form the intermolecular forces of attraction is maximum , so

mostly amino acids are present in solid state. That’s why they can be
separated from the important mixture.
2. Each amino acid has a specific pI value.
Calculation of pI value
Neutral 𝞪-amino acids

Acidic 𝞪-amino acids
If pKa < 7 ⟶ Acidic 𝞪 amino acid
If pKa > 7 ⟶ Basic 𝞪 amino acid


Peptides
These are those compounds which are formed by condensation of amino acids.
gly ala
IUPAC instructions
N-terminus ⟶ At LHS
C-terminus ⟶ At RHS
No of 𝞪 amino acids Peptides No of peptide linkages
2 Dipeptide 1
3 Tripeptide 2
4 Tetrapeptide 3
10 Decapeptide 9
n Based on it n-1
Peptides can form zwitter ion.

● Amino acids are the building block of proteins synthesis

because amino acids are used for the preparation of peptide
and polypeptides are basically proteins.
ORGANIC CHEMISTRY
PYQs-Biomolecules
The following questions are case-based questions. Read

the case carefully and answer the questions that follow.
Living systems are made up of various complex

biomolecules like carbohydrates, proteins, nucleic acids,
lipids, etc. Carbohydrates are optically active polyhydroxy
aldehydes or ketones or molecules which provide such units
on hydrolysis. They are broadly classified into three groups -
monosaccharides, oligosaccharides and polysaccharides.
Monosaccharides are held together by glycosidic linkages to
form disaccharides like sucrose, maltose or polysaccharides
like starch and cellulose.
Another biomolecule: proteins are polymers of α-amino acids

which are linked by peptide bonds. Ten amino acids are
called essential amino acids. Structure and shape of proteins
can be studied at four different levels i.e. primary, secondary,
tertiary and quaternary, each level being more complex than
the previous one.
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Solution:
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Solution:
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Solution:
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Solution:
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Solution:
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Maha Marathon : ORGANIC

Chapter Wise Weightage of chemistry CBSE Class 12

Haloalkanes & Haloarenes

Classification of Halogen Compounds

Monohalogen Dihalogen Polyhalogen

Contain 1 halogen atom 2 halogen atoms are Contain 3 halogen atoms

Classification based on the number of halogen atoms

Contain 1 halogen atom 2 halogen atoms are Contain 3 halogen

Halogen attached with Halogen attached with

Alkyl Allylic Benzylic

Classification of Halogen Compounds

Halogen attached with Halogen attached with

Classification of Halogen Compounds

Nomenclature of Halogen Compounds

Nomenclature of alkyl halide

Common Name IUPAC Name

Alkyl halide Haloalkane

Nomenclature of Halogen Compounds

Nomenclature of Halogen Compounds

Common name: Ethylidene chloride Ethylene dichloride

Nomenclature of aryl halides

● Haloarenes are the common as well as IUPAC names of

Nomenclature of Halogen Compounds

Nature of C-X Bond

Nature of C-X Bond

Various features of a C-X bond

Nature of C-X Bond

Various features of a C-X bond

● EN ↓ down the group, hence dipole moment which depends on the

Nature of C-X Bond

● Reactivity order of halogen acids : HI > HBr > HCl

Peroxide Absent Peroxide Present

● Addition of Br2 in CCl4 to an alkene resulting in discharge of

❏ Finkelstein Reaction: Alkyl Iodides are generally prepared

❏ Swarts Reaction: Alkyl Fluorides are generally prepared

❏ From hydrocarbons by electrophilic substitution

● The ortho and para isomers can be easily separated due to

❏ From amines by Sandmeyer’s reaction

Replacement of the diazonium group by iodine does not

Physical properties of any compound depend largely on

It’s mass The type of intermolecular

❏ Colour & Physical state:

● Boiling points of Chlorides, Bromides and Iodides are considerably

● For isomeric Haloalkanes :

● However, haloalkanes tend to dissolve in organic solvents

1. Reaction with Metals

Preparation of Grignard Reagent (RMgX)

In the Grignard reagent, the carbon-magnesium bond is covalent but

● Alkyl halides on treatment with Sodium metal in dry ether

● Number of C-atoms in alkane is twice of the number of

● Not preferred for the formation of Alkane with odd number

● Mixture of alkanes is formed.

2. Nucleophilic Substitution Reactions

Nucleophilic Substitution Reaction

SN2 Reaction SN1 Reaction

Retention, Inversion and Racemisation

Mechanism of SN2 Reaction

Mechanism of SN2 Reaction

● Polar aprotic solvent generally favour SN2 reactions such as

Mechanism of SN2 Reaction

Substitution Nucleophilic Unimolecular (SN1)

● Follows 1st order Kinetics