dichloromethane reaction

Discussion in 'Chemistry' started by ESSKAY, Jul 4, 2017.

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reaction product of hydration of dichloromethane

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  1. ESSKAY Registered Member

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    Can any one help me to solve this reaction that hydration of dichloromethane at high temperatures say more than 200 deg C.
     
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  3. exchemist Valued Senior Member

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    What you have written is not an English sentence, and your poll makes no sense, especially given that you seem to be asking something about organic chemistry, which, like inorganic chemistry, is part of chemistry.

    Can you clarify what it is you are enquiring about?
     
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  5. river Valued Senior Member

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    Can you not figure it out , exchemist ?
     
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  7. ESSKAY Registered Member

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    Thanks for your response Mr. Exchemist. I want to know what is the reaction scheme of hydration reaction of dichloromethane at high temperatures. Literatures proposed that HCl could be formed during the hydration reaction but when we look into the stoichiometry what else the other product, is that HClO (hypochlorous acid) ? Simply my question is CH2Cl2 + H2O gives 2HCl + HClO+H2 (g) is that correct?
     
  8. exchemist Valued Senior Member

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    5,875
    No. You have lost the carbon atom!

    The chloride ion, Cl- , is relatively stable due to the electronegativity of the chlorine atom. So just suppose Cl- gets knocked off CH2CL2. What is left, and how do you think it might react if it encounters a water molecule?
     
    Last edited: Jul 4, 2017
  9. exchemist Valued Senior Member

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    5,875
    I had the feeling this might have been homework, hence did not try to provide a complete answer straight away.

    Now that the homework has probably been handed in, I will try to close off the topic:

    It looks to me as if what happens is the carbocation picks up OH- from water, leading to ClCH2OH + H+ + Cl- , i.e. HCl. However the chlorinated methanol thus produced can itself quite easily lose a chloride ion and the proton from the hydroxyl group, generating another molecule of HCl and leading to an end product of O=CH2, i.e. formaldeyde. So that is my bet on what probably forms.
     
  10. ESSKAY Registered Member

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  11. ESSKAY Registered Member

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    Thanks Exchemist!! it looks very interesting and matches with my expectation. Because I could see some acidic effect on my compound when the reaction was conducted in HCl and DCM biphasic medium. Probably it might be produced during dissociation reaction, as you have derived.
     
  12. exchemist Valued Senior Member

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    5,875
    OK I should stress I do not know the answer to this. I am just thinking about what could happen. In the presence of surplus OH-, i.e. alkaline media, one might expect there could be an SN2 rather than SN1 first step. I don't think chloride is a brilliant leaving group.
     
  13. timojin Valued Senior Member

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    I would CH2Cl2 + 2H2O -----> CHOOH + 2HCl + H2

    Balanced for formic acid
     
    Last edited: Jul 6, 2017

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