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Acetoisonitrile on reaction with C2 H5 M...

Acetoisonitrile on reaction with `C_2 H_5 MgBr` followed by hydrolysis, gives compound `(A)`, which one further hydrolysis gives `(B)` and `( C)`.
`(B)` and `( C)` are :

A

`MeNH_2` and `EtCHO`

B

`EtNH_2` and `MeCHO`

C

`MeNH_2` and `EtCOOH`

D

`EtNH_2` and `MeCOOH`

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The correct Answer is:
To solve the problem, we will follow the steps of the reaction of acetoisonitrile with ethyl magnesium bromide (C2H5MgBr) and the subsequent hydrolysis. ### Step-by-Step Solution: 1. **Identify the Reactants**: Acetoisonitrile is CH3C≡N (where the isonitrile group is attached to the carbon of the carbonyl). The Grignard reagent is C2H5MgBr. 2. **Formation of the Intermediate**: When acetoisonitrile reacts with C2H5MgBr, the nucleophilic ethyl group (C2H5-) attacks the carbon atom of the isonitrile group. This results in the formation of an intermediate compound: \[ CH3C≡N + C2H5MgBr \rightarrow CH3C(C2H5)N^(-)MgBr^(+) \] Here, the nitrogen atom carries a negative charge. 3. **Hydrolysis of the Intermediate**: Upon hydrolysis (in acidic medium), the magnesium bromide (MgBr) will react with water, leading to the protonation of the nitrogen atom and the formation of a carbonyl compound: \[ CH3C(C2H5)N^(-)MgBr^(+)\ + H2O \rightarrow CH3C(C2H5)OH + NH3 \] The product formed here is an alcohol (compound A): \[ A: CH3C(C2H5)OH \] 4. **Further Hydrolysis**: The next step involves further hydrolysis of compound A. The alcohol group can undergo dehydration (loss of water) to form a carbonyl compound: \[ CH3C(C2H5)OH \rightarrow CH3C(C2H5)O + H2O \rightarrow CH3C(C2H5)O \] This leads to the formation of compound B (an amide) and compound C (an aldehyde): \[ B: CH3C(C2H5)O \quad (Methanamide) \] \[ C: CH3C(C2H5)O \quad (Ethyl aldehyde) \] 5. **Final Products**: After the complete hydrolysis, the final products are: - Compound B: Methanamide (CH3NH2) - Compound C: Propanal (C2H5CHO) ### Conclusion: Thus, the final compounds formed after the reactions are: - Compound B: Methanamide (CH3NH2) - Compound C: Propanal (C2H5CHO)
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CENGAGE CHEMISTRY ENGLISH-GRIGNARD REAGENTS AND ORGANOMETALLIC REAGENTS-Exercises (Single Correct)
  1. Methyl oxirane on reaction with CH3 MgBr, followed by hydrolysis, give...

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  2. Benzonitrile on reaction with C2 H5 MgBr, followed by hydrolysis, give...

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  3. Acetoisonitrile on reaction with C2 H5 MgBr followed by hydrolysis, gi...

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  4. .

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  5. Propane dithioic acid is prepared by the reaction of the following, fo...

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  6. Propylsulphinic acid is prepared by the reaction of the following, fol...

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  7. .

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  8. Ethanoic propanoic anhydride on reaction with excess of MeMgBr gives t...

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  9. Reactivity of MeMgBr with the following in the decreasing order is : ...

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  10. Product. The major product is :

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  11. Reactivity of with the following G.R in the decreasing order is : (...

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  12. .

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  13. Reactivity of EtMgBr with the following in the decreasing order is : ...

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  14. Reactivity of PhMgBr with the following in the decreasing order is : ...

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  15. Reactivity of PhMgBr with the following in the decreasing order is : ...

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  16. Reactivity of HCHO with the following G.R in the decreasing order is :...

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  17. Which of the following 3^@ alcohols does propyl ester give during reac...

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  18. Ethyl ester reacts with PrMgBr to give 2^@ alcohol. The alcohol is :

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  19. Methyl ester reacts with EtMgBr to give 3^@ alcohol The ester is :

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  20. Propyl ester reacts with isopropyl magnesium bromide to give 2^@ alcoh...

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