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Published on: 18/09/2019
Organic Compounds Containing Nitrogen
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Questions + Answers key
Take MCQ Chemistry Test

1.
Explain the following reactions:
(i) Gabriel phthalimide reaction
(ii) Coupling reaction
2.
What is Baker Mulliken's test? Discuss its chemistry.
3.
Predict the product of reaction of aniline with bromine in non-polar solvent such as CS2.
4.
What is the role of pyridine in the acylation reaction of amines?
5.
Why is NH2 group of aniline acetylated before carrying out nitration?
6.
What is the rol of HNO3 in the nitrating mixture used for nitration of benzene?
7.
How can you convert p-toluidine to 2-bromo-4-methylaniline?
8.
Draw the structures of different isomers corresponding to the molecular formula, C3H9N. Write the IUPAC names of the isomers which will liberate nitrogen gas on treatment with nitrous acid.
1.
(i) Gabriel's phthalimide synthesis: Phthalimide when treated with alcoholic potassium hydroxide is easily converted into potassium phthalimide which on treatment with alkyl halide followed by hydrolysis with acid or alkali yields phthalic acid and a primary amine.
(ii) Coupling reaction: It involves the reaction of benzene diazonium salts with phenols or aryl amines. Coupling of phenol takes place in mild alkaline solution while with aromatic 10 amines in mild, acidic medium.
2.
Both aliphatic and aromatic nitro compounds on reduction in neutral medium, i.e., Zn dust and NH4Cl solution, give the corresponding hydroxylamines.
\({ C }_{ 6 }{ H }_{ 5 }{ NO }_{ 2 }\quad \quad \overset { Zn/{ NH }_{ 4 }Cl,{ H }_{ 2 }O }{ \underset { \Delta }{ \longrightarrow } } \quad \quad { C }_{ 6 }{ H }_{ 5 }NHOH\\ Nitrobenzene\quad \quad \quad \quad \quad phenylhydroxylamine\\ \)
These hydroxylamines, when warmed with Tollens' reagent, are easily oxidized to the corresponding nitroso compounds and thus reduce Tollens' reagent to metallic silver
\({ C }_{ 6 }{ H }_{ 5 }NHOH+2{ \left[ Ag{ \left( { NH }_{ 3 } \right) }_{ 2 } \right] }^{ + }+2{ OH }^{ - }\longrightarrow { C }_{ 6 }{ H }_{ 5 }N=O+2Ag\downarrow +4{ NH }_{ 3 }+2{ H }_{ 2 }O\)
This reaction is called Baker Mulliken's test and is used as a test for detection of nitro group in organic compounds.
3.

4.
Pyridine and other bases are used to remove the side product(HCI) from the reaction mixture.
5.
It is because it will get oxidised with nitric acid if it is not acetylated.
6.
HNO acts as a base in the nitrating mixture (conc.HNO3+conc.H2SO4). H2SO4 acts on HNO3 to generate the electrophile, \({ NO }_{ 2 }^{ + }\) (nitronium ion)
7.

8.
Four structural isomers are possible.

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