MadSci Network: Chemistry

Subject: the reaction of CH3COOH and Cl2

Date: Thu Oct 29 19:45:31 1998
Posted by Ben
Grade level: 10-12
School: Morristown High School
City: Morristown State/Province: NJ
Country: USA
Area of science: Chemistry
ID: 909711931.Ch

Dear expert,
I read in a book that the reaction between the carboxylic acid (acetic 
acid?) and chlorine gives

        H    O
        |    ||
   Cl - C -  C - OH     +       HCl

What I would have expected was:

        CH3 - C - OCl    +    HCl

Since the thing that makes an acid an acid is how easily it can lose 
an H+ and still remain as stable as possible (or at least that's what 
I learned at Organic Chem over the summer), I would have expected 
of all the H's to replaced by the Cl radical, it would be the H+ from 
the carboxylic acid.  Another reason why I would think this is that H 
is not the typical leaving group, and Cl is not the one who usually 
does the substitution in organic reactions (maybe this isn't an SN1 or 
SN2 or E1 or E2 reaction in the first place?)  Thanks!

Re: the reaction of CH3COOH and Cl2

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