Magical Chemistry @ FTA ,+2 HSS/VHSS - Alcoholes Phenoles ,Ethers

HALO ALKANES AND HALO ARENES

+2 ORGANIC CHEMISTRY CHAPTER 1

Halo alkanes or Alkyl halides are having general formulae R-X Example CH3 Cl , C2H5Cl
Halo arenes or aryl halides having general formulae Ar X Example C6H5Cl
HALO ALKANES
On the Basis of Number of Halogen Atoms , Haloalkanes and haloarenes may be classified as follows:

They are further classified as primary, secondary or tertiary , according to the nature of carbon to
which halogen is attached. If halogen is attached to a primary carbon atom in an alkyl halide, the alkyl
halide is called primary alkyl halide or 1° alkyl halide. Similarly, if halogen is attached to secondary or
tertiary carbon atom, the alkyl halide is called secondary alkyl halide (2°) and tertiary (3°) alkyl halide,
respectively.

I . Methods of Preparation of Halo alkanes

a. From Alcohols ( R-OH )
Here the hydroxyl group of an alcohol is replaced by halogen .Many reactions are there
1. For the preparation of halo alkanes especially alkyl chloride thionyl chloride is preferred because in
this reaction alkyl halide is formed along with gases SO 2 and HCl which are in gaseous state and are
escapable, hence, the reaction gives pure alkyl halides.
R-OH + SOCl2 R-Cl + SO2 + HCl
2.For the preparation of alkyl bromide Constant boiling with HBr (48%) is used
R-OH +HBr (48%) R-Br + H2O
3.Good yields of RI may be obtained by heating alcohols with sodium or potassium iodide in 95%
ortho phosphoric acid.
95% H3PO4
R-OH +NaI / KI R-I + NaOH /KOH
/KOH
4. The reactions of primary and secondary alcohols with HCl require the presence of a catalyst, ZnCl 2 .
With tertiary alcohols, the reaction is conducted by simply shaking the alcohol with concentrated HCl at
room temperature.
R-OH(10 or 20alcohol)
alcohol) + HCl an. ZnCl2
R-Cl+ H2O
0
R-OH (3 alcohol ) + HCl R-Cl+ H2O
The order of reactivity of alcohols with a given halo acid is 3°>2°>1°.

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5.Other methods of preparations are

red P+ Br 2
R-OH R-Br + PBr3
red P+ I 2
R-OH R-I + PI3

3R-OH + PCl3 3 R-Cl + H3PO3

R-OH + PCl5 R-Cl + POCl3 + HCl

3R-OH + NaBr + H2SO4 R-Br + NaHSO4 +H2O

b.From Hydrocarbons
(I) From alkanes by free radical halogenation
Free radical chlorination or bromination of alkanes gives a complex mixture of isomeric mono-
and polyhalo alkanes

(II) From alkenes

(i) Addition of hydrogen halides: An alkene is converted to corresponding alkyl halide by reaction with
hydrogen chloride, hydrogen bromide or hydrogen iodide.

Propene yields two products, however only one

predominates as per Markovnikov’s rule.
( Halogen atom goes to that carbon atom which carries lesser number of H atom )

(ii) Addition of halogens:( Test for unsaturation)

In the laboratory, addition of bromine in CCl4 to an alkene
resulting in discharge of reddish brown colour of bromine .
It is an important method for the detection of double bond in a molecule. Because addition of Bromine
takes place across double bond and colour disappears .The addition results in the synthesis of vic-
dibromides, which are colourless

b. Halogen Exchange Reactions

a) Finkelstein reaction:
Alkyl chlorides or bromides when treated with NaI in dry acetone, alkyl iodides are formed. This
reaction is known as Finkelstein reaction.
R-X + NaI R-I + NaX (where X = Cl, Br)
b) Swarts reaction:
Alkyl chloride or bromide when treated with a metallic fluoride like silver fluoride (AgF ) or
Mercurous fluoride (Hg2F2) or cobalt fluoride (CoF 2) or Antimony fluoride (SbF3), alkyl fluoride is
formed. This reaction is known as Swarts reaction.
R-X + AgF R-F + AgX (where X = Cl or Br)

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II . Reactions of Halo alkanes

The reactions of halo alkanes may be divided into the following categories:
1. Nucleophilic substitution 2. Elimination reactions 3. Reaction with metals.
(1) Nucleophilic substitution reactions
Nucleophiles are electron rich species. Therefore, they attack on electron deficient centre of
substrate molecules(+ve centre) . The reaction in which a nucleophile replaces already existing
nucleophile in a molecule is called nucleophilic substitution reaction.
In this type of reaction, a nucleophile reacts with halo alkane (the substrate) having a
partial positive charge on the carbon atom bonded to halogen. A substitution reaction takes place
and halogen atom, called leaving group departs as halide ion. Since the substitution reaction is
initiated by a nucleophile, it is called nucleophilic substitution reaction.

Some Nucleophilic Substitution of Alkyl Halides (R–X) are

1. Reaction with aqueous alkali: Halo alkanes react with aq. NaOH or KOH to form alcohols.
R-X + KOH(aq) R-OH + KX
E.g.: CH 3 -CH 2 -Br + KOH(aq) CH 3 -CH 2 -OH + KBr
2. Reaction with water: Haloalkanes react with water to form alcohols.
R-X + H 2 O R-OH + HX
3. Reaction with Sodium alkoxide (R-ONa) [ Williamson’s ether synthesis] : Haloalkanes react with
sodium alkoxide to give ethers (R-O-R).
R-X + R-ONa R-O-R +NaX
e.g.: CH 3 -Br + CH 3 -CH 2 -ONa CH 3 -O-CH 2 -CH 3 + NaBr
4. Reaction with Sodium iodide (NaI): Alkyl halides (Chlorides or Bromides) react with sodium
iodide to form alkyl iodides.
R-X + NaI R-I + NaX [X = Cl or Br]
5. Reaction with ammonia: Alkyl halides react with alcoholic ammonia to give a mixture of 1 0 , 2
0 0

and 3 0 amines and quaternary ammonium salt.

0

R-X + NH 3 R-NH 2 + R 2 NH + R 3 N + R 4 N + X -
+ -

If ammonia is in excess, only primary amine is formed.

6. Reaction with KCN: Alkyl halides react with alcoholic KCN to give alkyl cyanides (R-CN).
R-X + KCN R-CN+ KX

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7. Reaction with Silver cyanide (AgCN): Alkyl halides react with AgCN to give alkyl isocyanides or
carbyl amines (R-NC). R-X + AgCN R-NC + AgX
8. Reaction with Potassium nitrite (KNO 2 ): Alkyl halides react with KNO 2 to give alkyl nitrite
(R-ONO). R-X + KNO 2 R-ONO + KX
9. Reaction with Silver nitrite (AgNO 2 ) : Alkyl halides react with AgNO 2 to give nitro alkane
(R-NO 2 ) R-X + AgNO 2 R-NO 2 + AgX
10. Reaction with Silver salts of carboxylic acid : Alkyl halides react with silver salts of carboxylic
acid (R-COOAg) to give esters (R-COOR). R-X + R-COOAg R-COOR + AgX
11. Reduction with LiAlH 4 : Alkyl halides when reduced with lithium aluminium hydride (LiAlH 4 ) to
give alkane. R-X + LiAlH 4 R-H + HX
Mechanism: This reaction has been found to proceed by two different mechanism which are
described below:
1. Substitution Nucleophilic bimolecular (SN 2) and 2.Substitution Nucleophilic unimolecular (SN1)
2 1

(a) Substitution nucleophilic bimolecular (S N 2)

2

SN2 reaction occurs in one steps. Here the incoming nucleophile OH interacts with alkyl
2

halide R-X causing the carbon-halogen bond to break while forming a new carbon-OH bond. These
two processes take place simultaneously in a single step and no intermediate is formed. But a highly
unstable transition state is formed. This mechanism proceeds through inversion of configuration, in
the same way as an umbrella is turned inside out when caught in a strong wind.
The reaction between methyl chloride CH 3Cl and hydroxide ion OH- to yield methanol
CH3OH and chloride ion Cl- follows a second order kinetics, i.e., the rate depends upon the
concentration of both the reactants.

The order of reactivity of alkyl halides towards SN 2 reaction is:

2

Primary halide > Secondary halide > Tertiary halide.

Tertiary halide due to three bulky group shows greater sterric hindrance

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Note:- Ambident nucleophiles.

Certain nucleophiles possess two nucleophilic centres and are called ambident nucleophiles.
Example :- Groups like cyanides and nitrites
Actually cyanide group is a hybrid of two contributing structures and therefore can act as a
nucleophile in two different ways [ (-)C≡N ↔ :C=N (-) ],
(-) (-)

i.e., linking through carbon atom resulting in alkyl cyanides and through nitrogen atom
leading to isocyanides.
Similarly nitrite ion also represents an ambident nucleophile with two different points of
linkage [ – O— N =O and NO2 ].
The linkage through oxygen results in alkyl nitrites while through nitrogen atom, it leads to
nitro alkanes.
2. Substitution nucleophilic unimolecular (SN 1):
1

SN1 reaction occurs in two steps. In the first step, the C—X bond undergoes slow cleavage to
produce a carbo cation and a halide ion. In the second step, the carbo cation is attacked by the
nucleophile to form the product. Here first step is the slowest and reversible. So it is the rate
determining step. Since this step contains only one reactant, it follows first order kinetics.
The reaction between tert- butyl bromide and hydroxide ion yields tert-butyl alcohol and
follows the first order kinetics, i.e., the rate of reaction depends upon the concentration of only one
reactant, which is tert- butyl bromide ( 2-bromo-2-methyl propane )

It occurs in two steps. In step I, the polarised C—Br bond undergoes slow cleavage to
produce a carbo cation and a bromide ion. The carbo cation thus formed is then attacked by
nucleophile in step II to complete the substitution reaction

step 1

step 2

Step I is the slowest and reversible. Since the rate of reaction depends upon the slowest
step, the rate of reaction depends only on the concentration of alkyl halide and not on the

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concentration of hydroxide ion. Further, greater the stability of carbo cation, greater will be its
ease of formation from alkyl halide and faster will be the rate of reaction.
In case of alkyl halides, 3 0 alkyl halides undergo SN 1 reaction very faster because of the high
0 1

stability of 3 0 carbo cations. The order of reactivity of alkyl halides towards S N1 and SN 2 reactions
0 1 2

as follows:
For a given alkyl group, the reactivity of the halide,
R–I> R–Br>R–Cl>>R–F.

Differences between SN1 and SN2 reactions

1.SN1 reaction proceeds in two step where as SN 2 reaction proceeds in a single step.
1 2

2.An intermediate (carbo cation) is formed in S N 1 reaction where as no intermediate is

1

formed in SN2 reaction.

3.Order is 1 for SN1 reaction where as 2 for SN 2 reactions
1 2

4.For optically active compounds,SN 1 reaction proceeds through retention of configuration.

1

For optically active compoundsSN2 reaction proceeds through inversion of configuration.

2

5.For SN1 the order of reactivity of alkyl halide is 3 0 > 2 0 > 1 0 .For SN 2 the order of reactivity
1 0 0 0 2

of alkyl halide is 1 0 > 2 0 > 3 0

0 0 0

Stereo chemical aspects of SN1 and SN2 reaction

(i) Optical activity:
When ordinary light is passed through nicol prism plane polarised light is obtained. When plane
polarised light is passed through optically active compounds it rotates the plane polarised light either to
the right, (, clockwise direction,) it is called dextrorotatory or the d-form and is indicated by placing a
positive (+) sign before the degree of rotation or towards left (anticlockwise direction), the compound is
said to be laevo-rotatory or the l-form and a negative (–) sign is placed before the degree of rotation.
Such (+) and (–) isomers of a compound are called optical isomers and the phenomenon is termed as
optical isomerism.

(ii )Assymetric carbon

Acarbon is said to be assymetric if four group attached to it are
different .
For such compounds the object is non-super imposable on its mirror images .

( iii) Chiral molecule The objects which are non-super imposable on their mirror image ( like a pair of
hands) are said to be chiral and this property is known as chirality.
chirality. Chiral molecules are optically

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active, .In chiral molecules object rotate plane polarised light to right direction , dextro rotatory d
(+ )while mirror image rotate plane polarised light to left direction , leavo rotatory l (- ) and vice versa
Example Butan-2-ol

E is mirror image of D; E is rotated by 180 o to get F and F is non super imposable on its mirror image D.
(iv) Achiral molecule:- The objects, which are, super imposable on their mirror images are called
achiral. These molecules are optically inactive. Butan-2-ol has four different groups attached to the
tetrahedral carbon and as
expected is chiral.
Example:- Propan-2-ol

B is mirror image of A; B is rotated by 180 o and C is obtained; C is superimposable on A.

( v) Enantiomers:-The
Enantiomers:-The stereo isomers related to each other as an object and non- super imposable mirror
images are called enantiomers. Enantiomers possess identical physical properties namely, melting point,
boiling point, refractive index, etc. They only differ with respect to the rotation of plane polarised light. If
one of the enantiomer is dextro rotatory, the other will be laevo rotatory.
Example butan -2-ol

(vi) Racemic mixture:- A mixture containing two enantiomers in equal proportions will have zero optical
rotation, as the rotation due to one isomer will be cancelled by the rotation due to the other
isomer( internal compensation). Such a mixture is known as racemic mixture or racemic modification.
modification. A
racemic mixture is represented by prefixing dl or (±) before the name, for example (±) butan-2-ol. The
process of conversion of enantiomer into a racemic mixture is known as racemisation.
Example:- (+)Tert.butyl chloride undergo SN1 reaction mechanism to give a dl mixture or
Racemic mixture. Therefore resultant product will be optically inactive because of internal compensation.
(vii) Retention: Retention of configuration is the preservation of the spatial arrangement of bonds to an
asymmetric centre during a chemical reaction .During a reaction, if no bond to the stereocentre is broken,
the product will have the same general configuration of groups around the stereocentre as that of
reactant. Such a reaction is said to proceed with retention of the configuration.

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( viii) Inversion:- if nucleophilic substitution taking place by SN 2 mechanism inversion in configuration

taking place. Here nucleophile attack from the opposite side of leaving group resulting in inversion in
configuration as shown in the example (+) Methyl chloride undergo SN2 mechanism to give (-)Methyl
alcohol.
2. Elimination reactions
When halo alkane is treated with alco KOH dehydrohalogenation taking place .Here
haloalkane with β-hydrogen atom is heated with alcoholic solution of potassium hydroxide,
elimination of hydrogen atom from β-carbon and a halogen atom from the α-carbon atom taking
place. As a result, an alkene is formed as a product. Since β-hydrogen atom is involved in
elimination, it is often called β -elimination.

Zaitsev 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.It is explained by Zaitsev rule . According to Alexander Zaitsev rule“ in
dehydrohalogenation reactions, the preferred product is that alkene which has the greater number
of alkyl groups attached to the doubly bonded carbon atoms.”
Thus, 2-bromopentane gives pent-2-ene as the major product.

3. Reaction with metals

a) With Mg
Alkyl magnesium halide, RMgX, is referred to as Grignard Reagents. These reagents are
obtained by the reaction of halo alkanes with magnesium metal in dry ether.
RX + Mg RMgX
Grignard reagents are highly reactive and react with water to give corresponding
hydrocarbons.

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It is therefore necessary to avoid even traces of moisture from a Grignard reagent. That is
why reaction is carried out in dry ether. On the other hand, this could be considered as one of the
methods for converting halides to hydrocarbons.
b)With Na ( Wurtz reaction )
Alkyl halides react with sodium in dry ether to give hydrocarbons containing double the
number of carbon atoms present in the halide. This reaction is known as Wurtz reaction

HALO ARENES
I . Methods of Preparation of Halo arenes
(i) From hydrocarbons by electrophilic substitution
Aryl chlorides and bromides can be easily prepared by electrophilic substitution of arenes
with chlorine and bromine respectively in the presence of Lewis acid catalysts like iron or iron(III)
chloride.

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 require the presence of an oxidising agent
(HNO3 , HIO4 ) to oxidise the HI formed during iodination.
Fluoro compounds are not prepared by this method due to high reactivity of fluorine.
(ii) From amines by Sandmeyer’s reaction:
When an aromatic primary amine (like aniline) is treated with HCl and sodium nitrite
(NaNO2) at cold condition an aromatic diazonium salt is formed. This reaction is called
Diazotisation.

When this diazonium salt is treated with HX in presence of cuprous halide (Cu 2X2), we get a halo
benzene. This reaction is called Sandmeyer’s reaction.

For the preparation of iodo benzene,

the diazonium salt is treated with potassium iodide (KI)

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II . Reactions of Halo arenes

a. Nucleiophilic substitution reactions
Aryl halides are extremely less reactive towards nucleophilic substitution reactions due to the
following reasons:
(i) Resonance effect : In haloarenes, the electron pairs on halogen atom are in conjugation with π-
electrons of the ring and the following resonating
structures are
possible.C—Cl bond acquires a partial double bond
character due to resonance. As a result, the bond
cleavage in halo arene is difficult than haloalkane and
therefore, they are less reactive towards nucleophilic substitution reaction.

(ii)Due to greater s charecter of sp2 hybridised c atom:- The sp2 hybridised carbon atom in halo arenes
with greater s-character is more electronegative and can hold the electron pair of C—X bond more
tightly than sp 3 -hybridised carbon in haloalkane with less s-chararcter. Thus, C—Cl bond length in
haloalkane is 177pm while in haloarene is 169 pm. Since it is difficult to break a shorter bond than a
longer bond, therefore, halo arenes are less reactive than haloalkanes towards nucleophilic substitution
reaction.

(iii) Instability of phenyl cation: In case of halo arenes, the phenyl cation formed as a result of self-
ionisation will not be stabilised by resonance and therefore, S N 1 mechanism is ruled out.

(iv) Because of the possible repulsion, it is less likely for the electron rich nucleophile to approach
electron rich arenes.
As a result of above reason substitution reaction in haloarenes not taking place normally. And
can takeplace under drastic conditions:example:-
Replacement by hydroxyl group
Chlorobenzene can be converted into phenol by heating in aqueous sodium hydroxide solution at
a temperature of 623K and a pressure of 300 atmospheres.

The presence of an electron withdrawing group (-NO 2 ) at ortho- and para-positions increases the
reactivity of haloarenes.

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b. Electrophilic substitution reactions

Halo group in Halo arenes is an ortho-para directing group. So the incoming electrophile
enters at ortho and para positions. Haloarenes undergo the
usual electrophilic reactions of the
benzene ring such as halogenation, nitration, sulphonation
and
Friedel-Crafts reactions.The o, p-directing influence of halogen
atom can be easily understood if we consider the resonating
structures of halo benzene as shown:
Due to resonance, the electron density increases more at ortho- and para-positions than at
meta-positions. 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 halo arenes occur slowly and require
more drastic conditions as compared to those in benzene.
Important Electrophilic substitution reactions are
(i) Halogenation:-Halo
Halogenation:- alkanes react with chlorine
in presence of anhydrous ferric chloride to form
o-dichlorobenzene and p-dichlorobenzene.

(ii) Nitration:-On nitration using Conc. HNO3 and Conc.

H2so4 (nitrating mixture), chlorobenzene gives o-nitro chloro
benzene and p-nitro chlorobenzene .in which later is major
product

(iii) Sulphonation:-On
Sulphonation:- sulphonation using Conc. H2SO4,
chloro benzene gives ortho chloro benzene sulphonic acid and
para chloro benzene sulphonic ( major product).

(iv) Friedel-Crafts alkylation Chloro benzene when

treated with methyl chloride (CH3-Cl) in presence of
anhydrous AlCl3, we get p-chloro toluene as the major product.

( v) Friedel-Crafts acylation : -Chloro benzene when

treated
with acetyl chloride (CH3-CO-Cl) in presence of anhydrous
AlCl3, we get p-chloro acetophenone as the major product.

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c.Reaction with metals

Wurtz-Fittig reaction
A mixture of an alkyl halide and aryl halide gives an alkylarene when treated with sodium in dry ether and
is called Wurtz-Fittig reaction.

Fittig reaction
Aryl halides also give analogous compounds when treated with sodium in dry ether, in which two aryl
groups are joined together. It is called Fittig reaction.

Polyhalogen Compounds
Carbon compounds containing more than one halogen atom are usually referred to as polyhalogen
compounds. Many of these compounds are useful in industry and agriculture. Some polyhalogen compounds are
described in this section.
1. Dichloromethane (Methylene chloride)
Uses
• it is widely used as a solvent
• as a paint remover,
• as a propellant in aerosols,
• and as a process solvent in the manufacture of drugs.
• It is also used as a metal cleaning and finishing solvent.
• Harmful effect
• Methylene chloride harms the human central nervous system.
• Exposure to lower levels of methylene chloride in air can lead to slightly impaired hearing and vision.
• Higher levels of methylene chloride in air cause dizziness, nausea, tingling and numbness in the fingers
and toes.
• In humans, direct skin contact with methylene chloride causes intense burning and mild redness of the
skin.
• Direct contact with the eyes can burn the cornea.
2. Trichloromethane (Chloroform)
Uses
• Chemically, chloroform is employed as a solvent for fats, alkaloids,iodine and other substances.
• The major use of chloroform today is in the production of the freon refrigerant R-22.
• It was once used as a general anaesthetic in surgery but has been replaced by less toxic,safer anaesthetics,
such as ether.
Harmful effect
• As might be expected from its use as an anaesthetic, inhaling chloroform vapours depresses the central
nervous system.
• Breathing about 900 parts of chloroform per million parts of air (900 parts per million) for a short time can
cause dizziness,fatigue, and headache.
• Chronic chloroform exposure may cause damage to the liver (where chloroform is metabolised to
phosgene) and to the kidneys, and some people develop sores when the skin is immersed in chloroform.
Chloroform is slowly oxidised by air in the presence of light to an extremely poisonous gas, carbonyl
chloride, also known as phosgene. It is therefore stored in closed dark coloured bottles completely filled so
that air is kept out.

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3. 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.
4. Tetrachloromethane (Carbon tetrachloride)
Uses
• It is produced in large quantities for use in the manufacture of refrigerants and propellants for aerosol cans.
• It is also used as feed stock in the synthesis of chlorofluorocarbons and other chemicals, pharmaceutical
manufacturing, and general solvent use.
• It was also 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.
Harmful effect
• There is some evidence that exposure to carbon tetrachloride causes liver cancer in humans.
• The most common effects are dizziness, light headedness, nausea and vomiting, which can cause
permanent damage to nerve cells.
• In severe cases, these effects can lead rapidly to stupor, coma, unconsciousness or death.
• Exposure to CCl 4 can make the heart beat irregularly or stop.
• The chemical may irritate the eyes on contact.
• When carbon tetrachloride is released into the air, it rises to the atmosphere and depletes the ozone layer.
Depletion of the ozone layer is believed to increase human exposure to ultraviolet rays, leading to
increased skin cancer, eye diseases and disorders, and possible disruption of the immune system.
5. Freons
Uses
• The chlorofluorocarbon compounds of methane and ethane are collectively known as freons.
• They are extremely stable, unreactive, non-toxic, non- corrosive and easily liquefiable gases.
• Freon 12 (CCl 2 F 2 ) is one of the most common freons in industrial use.
• It is manufactured from tetrachloro methane by Swarts reaction.
• These are usually produced for aerosol propellants, refrigeration and air conditioning purposes.
• By 1974, total freon production in the world was about 2 billion pounds annually.
Harmful effect
• Most freon, even that used in refrigeration, eventually makes its way into the atmosphere where it diffuses
unchanged into the stratosphere. In stratosphere, freon is able to initiate radical chain reactions that can
upset the natural ozone balance
6.p,p’-Dichlorodiphenyltrichloroethane(DDT)
Uses
• DDT, the first chlorinated organic insecticides
• Paul Muller discovered the effectiveness of DDT as an insecticide. Paul Muller was awarded the Nobel
Prize in Medicine and Physiology in 1948 for this discovery.
• It is effective against the mosquito that spreads malaria and lice that carry typhus.
Harmful effect
• Extensive use of DDT cause many species like insects for developing resistance to DDT
• It was also discovered to have a high toxicity towards fish.
• DDT is not metabolised very rapidly by animals; instead, it is
• deposited and stored in the fatty tissues.
• The use of DDT was banned in the United States in 1973,
although it is still in use in some other parts of the world.

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