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Why cannot aniline be prepared by Gabriel phthalimide synthesis?

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प्रश्न

Why cannot aniline be prepared by Gabriel phthalimide synthesis?

दीर्घउत्तर
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उत्तर

  1. Gabriel phthalimide synthesis is used for the preparation of aliphatic primary amines.
  2. It involves the nucleophilic substitution of alkyl halides by the anion formed by the phthalimide.
  3. But aryl halides do not undergo nucleophilic substitution with the anion formed by the phthalimide.
    Hence, aniline cannot be prepared by Gabriel phthalimide synthesis.
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अध्याय 13: Amines - Long answer questions

संबंधित प्रश्न

Write a short note on Hoffmann bromamide degradation.


Identify the compounds 'A' and 'B' in the following equation:


Write the chemical equation involved in the following reaction:

Hoffmann-bromamide degradation reaction


Give the structures of A, B and C in the following reactions :


Give the structures of A, B and C in the following reaction:

\[\ce{C6H5NO2 ->[Fe/HCl] A ->[HNO2][273 K] B ->[C6H5OH] C}\]


Why cannot aromatic primary amines be prepared by Gabriel phthalimide synthesis?


Give a plausible explanation for the following:

Why are amines less acidic than alcohols of comparable molecular masses?


Explain the mechanism of action of hydroiodic acid on 3-methylbutan-2-ol.


Arrange the following in the increasing order of their pKvalues:

C6H5NH2, C2H5NH2, C6H5NHCH3


Account for the following:
Gabriel phthalimide synthesis is not preferred for preparing aromatic primary amines.


Answer the following

Identify A and B in the following reactions.

\[\ce{C6H5CH2Br->[alco.][KCN]A ->[Na/ethanol]B.}\]


Answer the following

Explain Gabriel phthalimide synthesis.


Write reactions to prepare ethanamine from Acetonitrile.


Mendius reaction is used to convert _____________


Explain the following reaction with a suitable example.

Hofmann elimination reaction


Identify the product 'A' in the following reaction.

\[\ce{Aniline ->[(CH3CO)2O][Pyridine] A}\]


Identify the product obtained, when benzamide is treated with bromine and aqueous sodium hydroxide.


Identify the product obtained when benzyl chloride undergoes ammonolysis in presence of excess ammonia followed by the reaction with two moles of methyl iodide.


____________ can be prepared exclusively by Gabriel phthalimide synthesis.


Which of the following reactions is appropriate for converting benzamide to aniline?


Which of the following amines forms a clear solution when treated with benzene sulphonyl chloride and excess of potassium hydroxide?


Identify 'A' and 'B' in the following conversions.

\[\ce{CH3 - I ->[Alc. KCN][\Delta] A ->[Na/C2H5OH] B}\]


In aqueous phase the order of basic strength of alkylamine is ______.


Identify product B in the following reaction.

\[\ce{Aniline ->[NaNO2][HCl] A ->[KI] B}\]


Which of the following reagents would not be a good choice for reducing an aryl nitro compound to an amine?


The source of nitrogen in Gabriel synthesis of amines is ______.


The best reagent for converting 2–phenylpropanamide into 2-phenylpropanamine is ______.


Hoffmann Bromamide Degradation reaction is shown by ______.


Best method for preparing primary amines from alkyl halides without changing the number of carbon atoms in the chain is ______.


Which of the following compounds is the weakest Brönsted base?


Which of the following methods of preparation of amines will give same number of carbon atoms in the chain of amines as in the reactant?


Under which of the following reaction conditions, aniline gives p-nitro derivative as the major product?

(i) Acetyl chloride/pyridine followed by reaction with conc.\[\ce{H2SO4 }\] + conc. \[\ce{HNO3}\].

(ii) Acetic anyhdride/pyridine followed by conc.\[\ce{H2SO4}\] + conc.\[\ce{HNO3}\].

(iii) Dil. HCl followed by reaction with conc.\[\ce{H2SO4}\] + conc.\[\ce{HNO3}\].

(iv) Reaction with conc.\[\ce{HNO3}\] + conc.\[\ce{H2 SO4}\].


What is the product when \[\ce{C6H5CH2NH2}\] reacts with \[\ce{HNO2}\]?


How will you bring out the following conversion?


How will you carry out the following conversion?


How will you carry out the following conversions?


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

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


Describe Gabriel's phthalimide synthesis. (Give reaction)


The Gabriels' phthalimide synthesis is used in the synthesis of


Reduction of nitro alkanes yields which compound?


Acetamide and ethyl amide can be distinguished by reacting with.


Which of the following compound is expected to be most basic?


When primary amines are treated with HCl, the product obtained is which of the following?


A compound 'A' on reduction with iron scrap and hydrochloric acid gives compound 'B' with molecular formula C6H7N. Compound 'B' on reaction with CHCl3 and alcoholic KOH produces an obnoxious smell of carbylamine due to the formation of 'C'. Identify 'A', 'B' and 'C' and write the chemical reactions involved.


Which of the following reaction DOES NOT involve Hoffmann bromamide degradation?


Write the name of the product formed by the action of LiAlH4/ether on acetamide.


Write a short note on the following:

Ammonolysis


Write short note on the following:

Ammonolysis


Write a short note on Ammonolysis.


Write a short note on the following:

Ammonolysis


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