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Best method for preparing primary amines...

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

A

Hofmann bromamide reaction

B

Gabriel phthalimide

C

Sandmeyer reaction

D

reaction with `Nnh_(3)`

Text Solution

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The correct Answer is:
To prepare primary amines from alkyl halides without changing the number of carbon atoms in the chain, we can use the Gabriel phthalimide synthesis method. Here’s a step-by-step breakdown of the process: ### Step 1: Understanding the Reactants - **Phthalimide**: This is the starting material, which has the structure of a benzene ring with two carbonyl groups (C=O) at the ortho positions and an amine group (NH). - **Alkyl Halide (RX)**: This is the alkyl halide that we will react with phthalimide. Here, R represents an alkyl group and X represents a halogen (like Cl, Br, or I). ### Step 2: Formation of Potassium Phthalimide - When phthalimide is treated with alcoholic KOH, it undergoes deprotonation to form potassium phthalimide. - This involves the removal of a hydrogen atom from the nitrogen atom of phthalimide, resulting in a negatively charged nitrogen. ### Step 3: Nucleophilic Attack - The negatively charged nitrogen in potassium phthalimide acts as a nucleophile and attacks the alkyl halide (RX). - The halogen (X) is displaced, leading to the formation of an N-alkyl phthalimide. ### Step 4: Hydrolysis of N-alkyl Phthalimide - The N-alkyl phthalimide is then hydrolyzed to produce the primary amine and phthalic acid. - Hydrolysis can be performed either in acidic or basic conditions. In both cases, heating is often required. - The hydrolysis reaction breaks the bond between the nitrogen and the phthalimide ring, resulting in the release of the primary amine (RNH2) and phthalic acid. ### Step 5: Final Products - The final products of the reaction are the primary amine (RNH2) and phthalic acid. - Importantly, the number of carbon atoms in the primary amine remains the same as that in the original alkyl halide, fulfilling the requirement of the question. ### Conclusion Therefore, the best method for preparing primary amines from alkyl halides without changing the number of carbon atoms in the chain is **Gabriel phthalimide synthesis**. ---

To prepare primary amines from alkyl halides without changing the number of carbon atoms in the chain, we can use the Gabriel phthalimide synthesis method. Here’s a step-by-step breakdown of the process: ### Step 1: Understanding the Reactants - **Phthalimide**: This is the starting material, which has the structure of a benzene ring with two carbonyl groups (C=O) at the ortho positions and an amine group (NH). - **Alkyl Halide (RX)**: This is the alkyl halide that we will react with phthalimide. Here, R represents an alkyl group and X represents a halogen (like Cl, Br, or I). ### Step 2: Formation of Potassium Phthalimide - When phthalimide is treated with alcoholic KOH, it undergoes deprotonation to form potassium phthalimide. ...
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Knowledge Check

  • In which of the following compounds is the numbering of carbon atoms in the chain correct?

    A
    `overset(4)CH_3 - underset(C_2 H_5) underset(|) overset(3) CH - overset(2)CH = overset(1) CH_2`
    B
    `overset(1)CH_3 - underset(CH_3)underset(|)overset(CH_3)overset(2|)(C )- overset(3)CH_2 - overset(CH_3) overset(|)(""^4CH)- overset(5)CH_3`
    C
    `overset(1)CH_3 - overset(2)CH_2 - overset(OH) overset(|)(""^3 CH)- overset(4) CH_3`
    D
    `{:(overset(5)CH_3 - overset(4)CH_2 - overset(3)(CH)- overset(2)( C)-= overset(1)CH),(" "|),(" "CH_2 -CH_2 -CH_3):}`
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