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If one or more hydrogen atom is replaced in hydrocarbon by an equivalent number of halogen, the compounds formed are called halogen derivatives of hydrocarbons. Halogen derivatives are classified as aliphatic halogen compounds and aromatic halogen compounds. Aliphatic halogen compounds are formed by replacing one or more hydrogen of aliphatic hydrocarbons (alkanes, alkenes, and alkynes). Aliphatic halogen compounds are again divided as haloalkanes, haloalkenes and haloalkynes. Aromatic hydrocarbons are known as arenes. Halogen derivatives of arenes are termed as aromatic halogen compounds.

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When a hydrogen atom in an aromatic or aliphatic hydrocarbon is replaced with a halogen atom, haloalkanes and haloarenes are produced. Haloalkanes are generated when an H-atom is replaced in an aliphatic hydrocarbon, whereas Haloarenes are formed when the same H-atom is replaced in an aromatic hydrocarbon.

Question 44.

Haloalkanes undergo nucleophilic substitution whereas haloarenes undergo electrophilic substitution. Explain. (Comptt. Delhi 2012)

Answer:

Haloarenes (say chlorobenzene) is a resonance hybrid of the following five structures :


Resonance leads to lowering of energy and hence greater stability. On the other hand, no such resonance is possible in haloalkanes. Halogens directly attached to benzene ring are o, p-directing in electrophilic subsitution reactions. This is due to greater electron density at these positions in resonance.

Organohalogen compounds are organic compounds containing halogen atoms as part of their molecule. Haloalkanes (alkyl halides), haloarenes (aryl halides) and acid halides are some of the important classes of these compounds.

Organic compounds with halogen atoms in their molecules are known as organohalogen compounds. Haloalkanes (alkyl halides), haloarenes (aryl halides), and acid halides are examples of these compounds. A polar C-X functional group is present in their molecules, with X being a halogen atom such as F, Cl, Br, or I. The carbon atom has a partial positive charge, whereas the halogen atom, which is more electronegative than carbon, has a partial negative charge. Halogenated compounds are those that contain a halogen element, such as chlorine, bromine, fluorine, iodine, and so on.

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