Short Answer TypeChlorobenzene is extremely less reactive towards a nucleophilic substitution reaction. Give two reasons for the same?
1) Resonance effect: The electron pair on chlorine atom is in conjugation with the electrons of the benzene ring which results in the following resonance structures:
This results in delocalization of the electrons of C- Cl bond and a partial double bond character develop in the bond, which makes it difficult for the nucleophile to cleave the C- Cl bond.
2) The nucleophile suffers repulsion from the increased electron density on the benzene ring, as a result, the nucleophile is unable to make a close approach for the attack on the molecule.
Although chlorine is an electron withdrawing group, yet it is ortho-, Para-directing in electrophilic aromatic substitution reactions. Explain why it is so?
Long Answer TypeAnswer the following:
(i) Haloalkanes easily dissolve in organic solvents, why?
(ii) What is known as a racemic mixture? Give an example.
(iii) Of the two Bromo derivatives, C6H5CH(CH3)Br and C6H5CH(C6H5)Br, which one is more reactive in Sn1 substitution reaction and why?
Short Answer Type
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