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CH3CONH2 on reaction with NaOH and Br2...

`CH_3CONH_2` on reaction with NaOH and
`Br_2` in alcoholic medium gives :

A

`CH_3 CH_2 NH_2`

B

`CH_3 CH_2 Br`

C

`CH_3 NH_2`

D

`CH_3 COONa`

Text Solution

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The correct Answer is:
To solve the question regarding the reaction of `CH3CONH2` (acetamide) with NaOH and `Br2` in an alcoholic medium, we can break it down into several steps: ### Step-by-Step Solution: 1. **Identify the Reactants**: The reactants in this reaction are acetamide (`CH3CONH2`), sodium hydroxide (NaOH), and bromine (Br2) in an alcoholic medium. 2. **Understand the Reaction Conditions**: The presence of NaOH indicates a basic medium, which is crucial for the reaction mechanism. The alcoholic medium is also important as it influences the solubility and reactivity of the reactants. 3. **Formation of the Intermediate**: In a basic medium, NaOH will deprotonate the amide nitrogen, forming a negatively charged nitrogen species. This intermediate can then react with bromine. 4. **Bromination Step**: The negatively charged nitrogen (from the deprotonation) attacks one of the bromine atoms in Br2, leading to the formation of a bromo-substituted amide. The product at this stage is `CH3CONBr`. 5. **Formation of Nitrene**: The bromo-substituted amide undergoes a rearrangement where the bromine leaves, creating a nitrogen species known as nitrene. This step is crucial as it leads to the formation of an electron-deficient nitrogen. 6. **Migration of Methyl Group**: The electron deficiency at the nitrogen allows for the migration of the methyl group (CH3) from the carbonyl carbon to the nitrogen, forming a new compound. 7. **Final Product Formation**: The final product after the rearrangement and migration is methyl isocyanate (`CH3N=C=O`). This compound can further undergo hydrolysis in the presence of water (H2O) to yield the final product, which is methylamine (`CH3NH2`) and carbon dioxide (CO2). ### Final Answer: The reaction of `CH3CONH2` with NaOH and `Br2` in an alcoholic medium gives methyl isocyanate, which upon hydrolysis yields methylamine.

To solve the question regarding the reaction of `CH3CONH2` (acetamide) with NaOH and `Br2` in an alcoholic medium, we can break it down into several steps: ### Step-by-Step Solution: 1. **Identify the Reactants**: The reactants in this reaction are acetamide (`CH3CONH2`), sodium hydroxide (NaOH), and bromine (Br2) in an alcoholic medium. 2. **Understand the Reaction Conditions**: ...
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Knowledge Check

  • (CH_(3))_(3)CoNa on reaction with CH_(3)Br will give

    A
    `(CH_(3))_(3)COC(CH_(3))_(3)`
    B
    `CH_(3)OCH_(3)`
    C
    `CH_(3)CH_(2)OCH_(2)CH_(3)`
    D
    `(CH_(3))_(3)COCH_(3)`
  • Assertion : CH_3-overset(Br)overset(|)(CH)-CH_2CH_3 on reaction with alcoholic KOH gives CH_3CH=CHCH_3 as a result of dehydrohalogenation. Reason : Elimination reaction takes place in accordance with Markovnikov's rule.

    A
    If both assertion and reason are true and reason Is the correct explanation of assertion.
    B
    If both assertion and reason are true but reason is not the correct explanation of assertion.
    C
    If assertion is true but reason is false.
    D
    If both assertion and reason are false.
  • Hydrocarbon (CH_3)_3CH undergoes reaction with Br_2 and CI_2 in the presence of sunlight, if the reaction with Cl is highly reactive and that with Br is highly selective so no.of possible products respectively is (are)

    A
    2,2
    B
    2,1
    C
    1,2
    D
    1,1