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    If phenyl ethanoate was hydrolysed by sodium hydroxide why isn't it broken down into phenoland an ethanoate ion but instead an ethanoate ion, water and this ion that consists of a benzene ring attatched to an oxygen atom? The example of alkaline hydrolysis in the book does not mention producing water but the answer it gives says that water is produced. Is this only with esters that contain a benzene ring?:confused:
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    It's because of the acidic nature of phenol...lets abbreviate the benzene ring as ''Ph''

    After hydrolysis: PhOH + OH- ----> PhO- + H2O

    i.e. an acid-base reaction
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    (Original post by EierVonSatan)
    It's because of the acidic nature of phenol...lets abbreviate the benzene ring as ''Ph''

    After hydrolysis: PhOH + OH- ----> PhO- + H2O

    i.e. an acid-base reaction
    I was stuck on this question too! Thanks! I asked my teacher and he just couldn't explain it to me . . .then he started gettin ragy cos I'm like really stupid . . . . . .anyway, just to clarify, do all esters that contain a benzene ring produce water on hydrolysis as well as the ions?
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    (Original post by kawaii_innocence)
    I was stuck on this question too! Thanks! I asked my teacher and he just couldn't explain it to me . . .then he started gettin ragy cos I'm like really stupid . . . . . .anyway, just to clarify, do all esters that contain a benzene ring produce water on hydrolysis as well as the ions?
    Hi there

    In basic hydrolysis the overall process (with for example NaOH) is:

    R'CO2R + NaOH ----> R'CO2Na + ROH

    R can be any carbon chain/ring

    IF ROH is acidic (such as phenol) then this can react further with more base to produce water...(as above in previous post)

    So this only works when you produce a phenol compound after hydrolysis.

    Another example: PhCO2CH3 (Ph = 'benzene ring')

    So this produces PhCO2Na (sodium salt of benzoic acid) and CH3OH (methanol) - but methanol is not acidic, and thus doesn't react further with base.

    So when an ester of the form R'CO2R has R = benzene ring then water can be produced with more base.

    Hope that makes sense :p:
 
 
 
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