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Why cannot aniline be prepared by Gabriel phthalimide synthesis? - Chemistry

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प्रश्न

Why cannot aniline be prepared by Gabriel phthalimide synthesis?

दीर्घउत्तर

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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पाठ 13: Amines - Long answer questions

संबंधित प्रश्‍न

An aromatic compound 'A' of molecular formula C7H7ON undergoes a series of reactions as shown below. Write the structures of A, B, C, D and E in the following reactions :


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


Accomplish the following conversions Nitrobenzene to benzoic acid


Accomplish the following conversions: Benzamide to toluene


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


Give plausible explanation for each of the following :

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


Choose the most correct option.

Which of the following compounds will dissolve in aqueous NaOH after undergoing reaction with Hinsberg reagent?


Answer in one sentence.

Which amide does produce ethanamine by Hofmann bromamide degradation reaction?


Answer the following

Explain Gabriel phthalimide synthesis.


Mendius reaction is used to convert _____________


Write reactions to bring about the following conversions.

Acetamide to methylamine


Write reactions for the preparation of ethanamine using Gabriel phthalimide synthesis.


Identify compound 'B' in following series of reactions?

\[\ce{Acetonitrile ->[Na/alcohol] A ->[NaNO2/dil.HCI] B}\]


The end product C of the following reaction is

\[\ce{C2H5NH2 ->[HNO2] A ->[PCl5] B ->[NH3][Alcohol] C}\]


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


Identify the major product (B).


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

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


Which of the following amines cannot be prepared by Gabriel phthalimide synthesis?


Identify product B in the following reaction.

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


Which of the following does NOT give carbylamine test?


Nitro compounds are reduced by iron scrap and hydrochloric acid to yield one of the following compounds:


Quaternary ammonium salt is formed:


In order to prepare a 1° amine from an alkyl halide with simultaneous addition of one \[\ce{CH2}\] group in the carbon chain, the reagent used as source of nitrogen is ______.


The best reagent for converting, 2-phenylpropanamide into 1- phenylethanamine is ______.


Reduction of aromatic nitro compounds using \[\ce{Fe}\] and \[\ce{HCl}\] gives ______.


Among the following amines, the strongest Brönsted base is:


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?


Reduction of nitrobenzene by which of the following reagent gives aniline?

(i) \[\ce{Sn/HCl}\]

(ii) \[\ce{Fe/HCl}\]

(iii) \[\ce{H2 - Pd}\]

(iv) \[\ce{Sn/NH4OH}\]


What is the best reagent to convert nitrile to primary amine?


Write following conversions:

acetanilide `->` p-nitroaniline


Match the reactions given in Column I with the statements given in Column II.

  Column I   Column II
(i) Ammonolysis (a) Amine with lesser number of carbon atoms
(ii) Gabriel phthalimide synthesis (b) Detection test for primary amines.
(iii) Hoffmann Bromamide reaction (c) Reaction of phthalimide with \[\ce{KOH}\] and \[\ce{R-X}\]
(iv) Carbylamine reaction (d) Reaction of alkylhalides with \[\ce{NH3}\]

Assertion: Hoffmann’s bromamide reaction is given by primary amines.

Reason: Primary amines are more basic than secondary amines.


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

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


The Gabriels' phthalimide synthesis is used in the synthesis of


The compound X is which of the following?

\[\ce{CH3CN ->[Na + C2H5OH] x}\]


Ethylamine can be prepared by the action of bromine and caustic potash on which compound?


Reduction of nitro alkanes yields which compound?


Acetamide and ethyl amide can be distinguished by reacting with.


Give reasons for the following:

Ammonolysis of alkyl halides is not a good method to prepare pure primary amines.


Which of the following compound gives pink colour on reaction with phthalic anhydride in cone. H2SO4 followed by treatment with NaOH?


Which of the following amines can be prepared by Gabriel phthalimide reaction?


The amine 'A' when treated with nitrous acid gives yellow oily substance. The amine A is ______.


Which of the following would not be a good choice for reducing nitrobenzene to aniline?


Amides can be converted into amines by the reaction named ______.


Write short note on the following:

Ammonolysis


Write short note on the following:

Ammonolysis


Write short notes on the following:

Ammonolysis 


Write a short note on the following:

Ammonolysis


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