Q74 of 77 Page 192

Assertion : Acetanilide is less basic than aniline.

Reason : Acetylation of aniline results in decrease of electron density on nitrogen.


Note : In the following questions a statement of assertion followed by a statement of reason is given. Choose the correct answer out of the following choices.


Acetanilide is formed by the acetylation of aniline under the presence of a strong base like pyridine. The lone pair of electrons on nitrogen of acetanilide interacts with oxygen atom due to resonance, resulting in less availability of the electron pair on nitrogen for reaction.


This way, activating effect of –NHCOCH3 group is less than that of amino group and acetanilide is less basic than aniline.


In case of substituted aniline, electron releasing groups increase basic strength whereas electron withdrawing groups like decrease it.



The delocalization of electrons in the Acetanilide is show in below figure;


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72

Assertion : Only a small amount of HCl is required in the reduction of nitro compounds with iron scrap and HCl in the presence of steam.

Reason : FeCl2 formed gets hydrolysed to release HCl during the reaction.


Note : In the following questions a statement of assertion followed by a statement of reason is given. Choose the correct answer out of the following choices.


 73

Assertion : Aromatic 1° amines can be prepared by Gabriel Phthalimide Synthesis.

Reason : Aryl halides undergo nucleophilic substitution with anion formed by phthalimide.


Note : In the following questions a statement of assertion followed by a statement of reason is given. Choose the correct answer out of the following choices.


 75

A hydrocarbon ‘A’, (C4H8) on reaction with HCl gives a compound ‘B’, (C4H9Cl), which on reaction with 1 mol of NH3 gives compound ‘C’, (C4H11N). On reacting with NaNO2 and HCl followed by treatment with water, compound ‘C’ yields an optically active alcohol, ‘D’. Ozonolysis of ‘A’ gives 2 mols of acetaldehyde. Identify compounds ‘A’ to ‘D’. Explain the reactions involved.

 76

A colourless substance ‘A’ (C6H7N) is sparingly soluble in water and gives a water soluble compound ‘B’ on treating with mineral acid. On reacting with CHCl3 and alcoholic potash ‘A’ produces an obnoxious smell due to the formation of compound ‘C’. Reaction of ‘A’ with benzenesulphonyl chloride gives compound ‘D’ which is soluble in alkali. With NaNO2 and HCl, ‘A’ forms compound ‘E’ which reacts with phenol in alkaline medium to give an orange dye ‘F’. Identify compounds ‘A’ to ‘F’.