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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

How is ethyl amine prepared from methyl iodide?


How are propan-1-amine and propan-2-amine prepared from oxime?


Write the chemical equation involved in the following reaction:

Hoffmann-bromamide degradation reaction


Illustrate the following reaction giving suitable example in each case:Gabriel phthalimide synthesis


Accomplish the following conversion:

Nitrobenzene to benzoic acid


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

\[\ce{CH3CH2Br ->[KCN] A ->[LiAlH4] B ->[HNO2][0^\circ C] C}\]


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

\[\ce{C6H5NO2 ->[Fe/HCl] A ->[NaNO2 + HCl][273 K] B ->[H2O/H+][\Delta] C}\]


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

\[\ce{CH3COOH ->[NH3][\Delta] A ->[NaOBr] B ->[NaNO2/HCl] C}\]


Arrange the following in the increasing order of their pKvalues:

C6H5NH2, C2H5NH2, C6H5NHCH3


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


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


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

Identify A and B in the following reactions.

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


Answer the following

Write a reaction to convert acetic acid into methylamine.


Answer the following

Explain Gabriel phthalimide synthesis.


Write reactions to bring about the following conversions.

Acetamide to methylamine


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


Alkyl cyanides on reduction by sodium and ethanol give primary amines. This reaction is called as ____________.


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


Which of the following amines exhibits maximum degree of intermolecular hydrogen bonding?


Identify the major product (B).


What is the molar mass of the amine formed when acetamide undergoes Hofmann bromamide degradation?


The reduction of alkyl cyanide with sodium and ethanol to give primary amines is, ____________.


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


Which of the following compounds is obtained when quaternary ammonium hydroxide is strongly heated?


Given below are two statements labelled as Assertion (A) and Reason (R).

Assertion (A): Alkyl halides are insoluble in water.

Reason (R): Alkyl halides have halogen attached to sp3 hybrid carbon.

Select the most appropriate answer from the options given below:


Amongst the following, the strongest base in aqueous medium is ______.


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


Amongst the given set of reactants, the most appropriate for preparing 2° amine is ______.


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


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


Hoffmann Bromamide Degradation reaction is shown by ______.


Which of the following compounds is the weakest Brönsted base?


Among the following amines, the strongest Brönsted base is:


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

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

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

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

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


Which of the following reactions are correct?

(i)

(ii)

(iii)

(iv)


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


Suggest a route by which the following conversion can be accomplished.


How will you bring out the following conversion?


How will you carry out the following conversion?


Assertion: Only a small amount of \[\ce{HCl}\] is required in the reduction of nitro compounds with iron scrap and \[\ce{HCl}\] in the presence of steam.

Reason: \[\ce{FeCl2}\] formed gets hydrolysed to release \[\ce{HCl}\] during the reaction.


The compound X is which of the following?

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


In the given reaction what is the X?

\[\begin{array}{cc}
\ce{O}\phantom{.......................}\\
||\phantom{.......................}\\
\phantom{}\ce{R - C - OH <-[H3O] Χ ->[H] RCH2NH2}
\end{array}\]


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


Which of the following CANNOT be prepared by ammonolysis of alkyl halide?


Give reasons for the following:

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


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


Identify the product ‘C’ in the following reaction.

\[\ce{Aniline ->[(CH3CH)2O][Pyridine] A ->[Br2][CH3COOH] B ->[H^+ or OH^-] C}\]


Write short note on the following:

Ammonolysis


Assertion: Amimonolysis of alkyl halides involves the reaction between alkyl halides and alcoholic ammonia.

Reason: Ammonolysis of alkyl halides produces secondary amines only.


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