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By JAGRAN JOSH
OCT 17, 2016, 19:17 IST
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• Classification of haloalkanes
• Preparation of haloalkanes
• Reactions of Haloalkanes
• Stereoisomerism
• Reactions of haloarenes
Classification of Haloalkanes:
The halogen derivatives of hydrocarbons may be classified as fluoro, chloro, bromo or iodo
compounds according to the type of halogen present.
Depending upon the number of halogens present, the halogen derivatives can be classified as
mono, di, tri or polyhalo compounds.
On the basis of the nature of the carbon to which halogen atom is attached, halogen derivatives
are classified as 1o, 2o, 3o, allylic, benzylic, vinylic and aryl derivatives.
For example:
1o, 2o and 3o halides: halogen atom is bonded to primary, secondary or tertiary carbon atom of
an an alkyl group.
Allylic halides: Halogen atom is bonded to an sp3-hybridised carbon atom next to carbon-
carbon double bond (C=C) i.e. to an allylic carbon.
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X is more electronegative than carbon. So, the C-X bond is polarized with C having a partial
positive charge and X having a partial negative charge.
Chlorination or bromination of alkane usually gives a complete mixture of isomeric mono and
poly halo alkanes.
The hydroxyl group of an alcohol is replaced by halogen on reaction with concentrated halogen
acids, phosphorus halides or thionyl chloride to give the corresponding alkyl halide.
4. By halogen exchange:
Alkyl iodides can be prepared by the reaction of alkyl chlorides/ bromides with NaI in dry acetone.
Preparation of haloarenes
This involves the direct halogenation of benzene ring in the presence of Lewis acid catalysts like
iron or iron (III) chloride.
2. By Sandmeyer’s reaction:
Aniline is treated with sodium nitrite to give a diazonium salt which is then treated with cuprous
chloride or cuprous bromide to produce the corresponding aryl halide:
This involves the conversion of aryl amines to aryl fluorides via diazotisation and subsequent
thermal decomposition of the derived aromatic fluoborate to produce the corresponding aryl
fluoride.
Physical properties of haloderivatives are different than those of the simple hydrocarbons. These
are described below:
• Alkyl halides are colourless when pure but bromides and particularly iodides develop colour
when exposed to light.
• Halogen compounds have higher boiling points than the corresponding hydrocarbon. This is
because the greater polarity as well as higher molecular mass as compared to the parent
hydrocarbon causes the intermolecular forces of attraction (dipole-dipole and van der Waals) to
be stronger in the halogen derivatives.
• For monohalogen compounds, the boiling point increases with increasing molecular mass of
the halogen group with a fixed hydrocarbon group,
• All halogen derivatives of hydrocarbon are insoluble in water as they are incapable of forming
hydrogen bonds with water but alkyl halides are soluble in non-polar solvents, R‒F < R‒Cl < R‒Br
< R‒I
• The density increases with increasing number and the atomic mass of the halogen.
Reactions of Haloalkanes
The reactions of haloalkanes may be divided into the three main categories:
Nucleophilic substitution: A nucleophile attacks the haloalkane which is having a partial positive
charge on the carbon atom bonded to halogen. Halide ion separates following a substitution
reaction.
For the same alkyl group, as we move from F to I, strength of C−X bond decreases, therefore, the
reactivity order is: R− I > R−Br > R−Cl > R−F
The nucleophilic substitution reaction can proceed via SN1 mechanism or SN2mechanism.
place in two steps, first step being the rate determining step involves the formation of carbonium
ion.
The reactivity
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order of haloalkanes
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towards SN 1reaction is:
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1° R−X < 2° R−X < 3° R−X
place in one step. The incoming nucleophile interacts with alkyl halide causing the C−X bond
bond to break while forming a new C−OH bond.
Elimination reactions:
When a haloalkane with β-hydrogen atom is heated with alcoholic solution of potassium
hydroxide, there is elimination of hydrogen atom from β-carbon and a halogen atom from the α-
carbon atom resulting in the formation of an alkene. The reaction follows the Saytzeff rule which
states that “In dehydrohalogenation reactions, the preferred product is that alkene which has the
greater number of alkyl groups attached to the doubly bonded carbon atoms.”
Reaction with Magnesium: Alkyl halides react with magnesium in the presence of dry ether to
form corresponding alkyl magnesium halide which is also known as Grignard’s reagent.
2R‒X + 2 Na → R ‒ R + 2NaX
Stereoisomerism
Stereoisomerism is due to the different orientation of atoms or groups in space. There are two
types of stereoisomerism:
(i) Geometrical isomerism: It arises due to the presence of like groups on the same side of the
plane (cis) or on the opposite side of the plane (trans).
(ii) Optical isomerism: It arises due to the presence of non-superimposable mirror images.
Conditions for optical isomerism to take place are:
• Presence of chiral carbon or asymmetric carbon, i.e., The C attached to four different groups.
Chiral carbon is denoted as C*.
• Dextrorotatory (+): These rotate the plane polarised light in a clockwise direction
• Laevorotatory (–): These rotate the plane polarised light in an anticlockwise direction
Racemic mixture
A mixture containing two enantiomers in equal proportions is called racemic mixture. A recemic
mixture is optically inactive as the effect of one isomer gets cancelled by another isomer.
Racemisation
Reactions of Haloarenes
Nucleophilic substitution:
Aryl halides are almost unreactive towards nucleophilic substitution reaction. This is because of
double character of C – X bond due to resonance. Therefore, it is difficult to remove X from C – X
bond.
reactions:
Presence of an electron withdrawing group like NO2 group increases the reactivity of aryl halides
NO2 group increases the reactivity more when present at o- and p- position due to the increased
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