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Haloalkanes , Haloarenes & Phenols - Reasoning questions & Answers

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1.) Why do haloalkenes under go nucleophillic substitution whereas haloarenes
under go electophillic substitution .
Ans. Due to more electro negative nature of halide atom in haloalkanes carbon atom
becomes slightly positive and is easily attacked by nucleophillic reagents.
While in haloarenes due to resonance, carbon atom becomes slightly
negative and attacked by electrophillic reagents.
reagents.
2.) When an alkyl halide is treated with ethanolic solution of KCN, the major
product is alkyl cyanide where as if alkyl halide is treated with AgCN,the
major product is alkyl isocyanide.
Ans. KCN is ionic they can attach through C or N but C-C bond is strong than C-N
bond. So alkyl cyanide is the major product but AgCN is covalent so more
electronegative N can attach to C and forms isocyanides.
3.) How do primary , secondary & tertiary alcohols differ in terms of dehydrogenation?

Ans.
4.) Why are the reaction of alcohol /phenol with acid chloride in the presence of
pyridine ?
Ans. Because esterification reaction is reversible and presence of base (pyridine )
nuetralises HCl produced during reaction thus promoting forward reaction .
5.) Explain why o-nitrophenol is more acidic than o-methoxy phenol ?
Ans. -NO2 group is electron with - drawing group, e-density on O decreases and loss

of H+ is easy whereas –OCH3 group is electron releasing group , which increases e-
density on O , which makes difficult to the loss of H+, hence are less acidic .
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