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Methyl oxirane on reaction with CH3 MgBr...

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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The correct Answer is:
To determine the mechanism by which methyl oxirane reacts with methyl magnesium bromide (CH₃MgBr) followed by hydrolysis to form an alcohol, we can follow these steps: ### Step 1: Identify the Reactants Methyl oxirane is an epoxide, which is a three-membered cyclic ether. The structure of methyl oxirane is as follows: ``` O / \ CH3 CH ``` ### Step 2: Reaction with Methyl Magnesium Bromide When methyl oxirane reacts with methyl magnesium bromide (a Grignard reagent), the nucleophilic carbon (from the Grignard reagent) attacks the less hindered carbon atom of the epoxide. This is a characteristic feature of an SN2 mechanism, where the nucleophile attacks the electrophile and simultaneously displaces the leaving group. ### Step 3: Mechanism of the Reaction 1. The nucleophilic carbon from CH₃MgBr attacks the carbon atom adjacent to the oxygen in the epoxide. 2. This results in the opening of the epoxide ring and the formation of a tetrahedral intermediate. 3. The oxygen atom becomes negatively charged, and the bond between the carbon and oxygen is broken. ### Step 4: Hydrolysis After the epoxide ring opens, hydrolysis occurs. The negatively charged oxygen will react with water (or H₃O⁺) to form an alcohol. The final product will be a secondary alcohol due to the formation of a new carbon-carbon bond. ### Step 5: Final Product The final product after hydrolysis is a secondary alcohol, which can be represented as follows: ``` OH / CH3-CH-CH3 ``` ### Conclusion The mechanism by which methyl oxirane reacts with CH₃MgBr followed by hydrolysis is an SN2 mechanism, resulting in the formation of a secondary alcohol.

To determine the mechanism by which methyl oxirane reacts with methyl magnesium bromide (CH₃MgBr) followed by hydrolysis to form an alcohol, we can follow these steps: ### Step 1: Identify the Reactants Methyl oxirane is an epoxide, which is a three-membered cyclic ether. The structure of methyl oxirane is as follows: ``` O / \ ...
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CENGAGE CHEMISTRY ENGLISH-GRIGNARD REAGENTS AND ORGANOMETALLIC REAGENTS-Exercises (Single Correct)
  1. .

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  2. Ethylmercaptan is prepared by the reaction of the following, followed ...

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  3. Methyl oxirane on reaction with CH3 MgBr, followed by hydrolysis, give...

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

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

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  6. .

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

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

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  9. .

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

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

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  12. Product. The major product is :

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

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  14. .

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

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

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

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

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

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

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