Prepare Methyl Iodide Using SN2 Mechanism

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In summary, the conversation discusses a problem involving the preparation of methyl iodide using a methyl halide and an appropriate solvent. The person is confused about how to replace a halide with an iodide ion, but is reminded that iodide is the best leaving group and the solvent can make a difference. An example of a displacement reaction with methyl bromide and KI is provided, and it is suggested to use an aprotic solvent such as DMSO, DMF, or acetone.
  • #1
Mind_It
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Homework Statement


Hi folks! :)
I have a problem with the following problem.
Take any methyl halide and prepare methyl iodide.Choose the appropriate solvent.

Now what i know is here we are going by SN2 mech and replacing a halide by iodide ion.But the problem i am facing is how can i replace a other halide by a iodide ion because my book says iodide is the best leaving group among all halides.So i am confused how will this happen. ?
 
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  • #2
Yes, iodide is the best leaving group. But the solvent can make the difference. For example, the Kharasch addition in the presence of H2O2 breaks the Markonikov's rule. I'm sorry I don't have the details of this reaction, but will check into it.
 
  • #3
You can do a displacement reaction with methylbromide:

CH3Br + KI ----> CH3I + KBr

You might want to use an aprotic solvent such as DMSO, DMF or acetone.
 

1. How is methyl iodide prepared using SN2 mechanism?

The SN2 (substitution nucleophilic bimolecular) mechanism is a type of reaction used for preparing methyl iodide. In this mechanism, a nucleophile (such as hydroxide ion) attacks a primary alkyl halide (such as methyl chloride) to form a new carbon-nucleophile bond, while the leaving group (such as chloride ion) is expelled. This reaction is typically carried out in an aprotic solvent, such as acetone or acetonitrile, and in the presence of a strong base, such as sodium hydroxide. The resulting product is methyl iodide.

2. What is the purpose of using SN2 mechanism for preparing methyl iodide?

The SN2 mechanism is preferred for preparing methyl iodide because it offers a straightforward and efficient route. It allows for the direct substitution of a leaving group with an incoming nucleophile, resulting in the formation of a new carbon-nucleophile bond. This method also has a high yield and can be conducted under mild conditions, making it a convenient and practical choice for synthesizing methyl iodide.

3. What are the starting materials required for preparing methyl iodide using SN2 mechanism?

The starting materials required for preparing methyl iodide using SN2 mechanism are a primary alkyl halide (such as methyl chloride) and a strong base (such as sodium hydroxide). An aprotic solvent (such as acetone or acetonitrile) is also needed to facilitate the reaction. Additionally, methyl iodide can be prepared from methanol and hydroiodic acid in the presence of a dehydrating agent, such as sulfuric acid.

4. What are some precautions to take when preparing methyl iodide using SN2 mechanism?

When carrying out the SN2 reaction, it is important to use proper safety precautions as both the starting materials and the product can be hazardous. Methyl iodide is a highly toxic and corrosive compound, and should be handled with care. It is also important to conduct the reaction in a well-ventilated area to avoid exposure to toxic fumes. Protective gear, such as gloves, goggles, and a lab coat, should be worn at all times to ensure safety.

5. Can other alkyl iodides be prepared using the SN2 mechanism?

Yes, other alkyl iodides can be prepared using the SN2 mechanism. The reaction follows the same principle, where a primary alkyl halide is treated with a strong base and an aprotic solvent to produce the corresponding alkyl iodide. However, the reactivity and yield of the reaction may vary depending on the structure of the alkyl halide. For example, tertiary alkyl halides may undergo competing reactions, resulting in a lower yield of the desired product.

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