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The reduction of a nitrile by LiAlH(...

The reduction of a nitrile by LiAlH_( 4 ) produes :

A

Primary amine

B

Secondary amine

C

Tetiary amine

D

Amide

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The correct Answer is:
To solve the question regarding the reduction of a nitrile by LiAlH4, we can break down the process into several steps. ### Step-by-Step Solution: 1. **Understanding the Reactants**: - A nitrile has the general formula \( R-C \equiv N \), where \( R \) is an alkyl or aryl group. - Lithium aluminum hydride (LiAlH4) is a strong reducing agent that provides hydride ions (H-) for reduction reactions. 2. **Mechanism of Reduction**: - When nitrile is treated with LiAlH4, the hydride ion from LiAlH4 acts as a nucleophile and attacks the electrophilic carbon atom of the nitrile. - This leads to the formation of a tetrahedral intermediate. 3. **Formation of Imine**: - The nucleophilic attack results in the formation of an intermediate that can rearrange to form an imine (R-C(=N)-H) and release a negative charge on nitrogen. 4. **Further Reduction**: - The imine can be further reduced by another equivalent of LiAlH4, leading to the formation of a primary amine (R-CH2-NH2). 5. **Final Product**: - Therefore, the overall reaction of nitrile with LiAlH4 results in the formation of a primary amine. ### Conclusion: The reduction of a nitrile by LiAlH4 produces a primary amine.
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Explore conceptually related problems

LiAlH_(4) is used as :

What are nitriles ?

Alkyl cyanides (CH_(3)CN) when treated with hydrogen in presence of Pt or with LiAlH_(4) produces same carbon number compound. What is the formula of that compound ?

A : Esters on reduction with LiAlH_(4) forms alcohols. R : Esters having at least two alpha -Hydrogen atoms undergo Claisen condensation.

Assertion : LiAlH_(4) is more reactive and less selctive than NaBH_(4) as a reducing agent. Reason : LiAlH_(4) reduces both aldehydic group and double bond in conjugate position while NaBH_(4) does not.

Stephen's reduction converts nitriles into:

Knowledge Check

  • The reaction of C_(6)H_(5)CH=CHCHO with LiAlH_(4) gives :

    A
    `C_(6)H_(5)CH_(2)CH_(2)CH_(2)OH`
    B
    `C_(6)H_(5)CH=CHCH_(2)OH`
    C
    `C_(6)H_(5)CH_(2)CH_(2)CHO`
    D
    `C_(6)H_(5)CH_(2)CHOHCH_(3)`
  • Carbon-oxygen double bond are easily reduced by NaBH_(4) or LiAlH_(4) . The actual reducing agent in these reduction is hydride ion (H^(-)) . The metal-hydrogen bond in LiAlH_(4) is more polar than metal-hydrogen bond in NaBH_(4) . As a result LiAlH_(4) is strong reducing agent than NaBH_(4) . Esters, carboxylic acids, amides cannot be reduced by NaBH_(4) . The carbonyl group of amide reduced to methylene group by LiAlH_(4) . , Identify X:

    A
    B
    C
    D
  • Carbon-oxygen double bond are easily reduced by NaBH_(4) or LiAlH_(4) . The actual reducing agent in these reduction is hydride ion (H^(-)) . The metal-hydrogen bond in LiAlH_(4) is more polar than metal-hydrogen bond in NaBH_(4) . As a result LiAlH_(4) is strong reducing agent than NaBH_(4) . Esters, carboxylic acids, amides cannot be reduced by NaBH_(4) . The carbonyl group of amide reduced to methylene group by LiAlH_(4) . Find the correct product of the following reaction :

    A
    B
    C
    D
    no reaction
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