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The reaction of RCN with R'MgX, followed...

The reaction of RCN with R'MgX, followed by hydrolysis gives

A

an aldehyde

B

a ketone

C

`2^@` alcohol

D

`3^@` alcohol

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem of what compound is formed when RCN reacts with R'MgX followed by hydrolysis, we can break down the process step by step. ### Step-by-Step Solution: 1. **Identify the Reactants**: - We have RCN, which is a nitrile (where R is an organic group and C is bonded to a nitrogen atom with a triple bond). - We also have R'MgX, which is a Grignard reagent (where R' is another organic group, Mg is magnesium, and X is a halogen). 2. **Reaction of Nitrile with Grignard Reagent**: - When RCN reacts with R'MgX, the nucleophilic carbon (C) in the nitrile reacts with the electrophilic carbon (C) in the Grignard reagent. - The reaction can be represented as: \[ RCN + R'MgX \rightarrow R-C(=N)R' + MgX \] - Here, the carbon of the nitrile (C≡N) becomes a carbon bonded to R' and has a double bond with nitrogen (C=N). 3. **Formation of an Imine**: - The product from the above reaction is an imine (or an intermediate compound) where the nitrogen is still attached to the carbon. - The structure can be represented as: \[ R-C(=N)R' \] 4. **Hydrolysis of the Imine**: - The next step involves hydrolysis, where the imine reacts with water (H2O) in the presence of an acid. - During hydrolysis, the imine bond (C=N) is broken, and the nitrogen is protonated, while the carbon gets an oxygen from water. - This reaction can be summarized as: \[ R-C(=N)R' + H2O \rightarrow R-C(=O)R' + NH3 \] - The product of this hydrolysis is a ketone (R-C(=O)R') and ammonia (NH3). 5. **Final Product**: - The final compound obtained from this reaction sequence is a ketone, specifically R-C(=O)R'. ### Conclusion: The compound formed from the reaction of RCN with R'MgX followed by hydrolysis is a **ketone**.
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Knowledge Check

  • The reaction of RCN with RMgX following by hydrolysis gives

    A
    an aldehydes
    B
    an ketones
    C
    `2^(0)` alcohols
    D
    `3^(0)` alcohols
  • Reaction of with RMgX followed by hydrolysis produces

    A
    `RCHOHR`
    B
    `R CHOHCH_(3)`
    C
    `R_(2)CHCH_(2)OH`
    D
    `RCH_(2)CH_(2)OH`
  • Methyl oxirane on reaction with CH_3 MgBr , followed by hydrolysis, gives alcohol. By which of the following mechanisms does the reaction proceed ?

    A
    `SN^1`
    B
    `SN^2`
    C
    `SN^i`
    D
    `SE`
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