6(e) For acid-catalysed hydrolysis of substituted benzoic esters (in 99.9% H2SO4) the rate-determining step follows protonation: H* ö-Et H O-Et RDS + H₂O + H₂O R R R When rates are measured and their logarithms are plotted against the Hammett substituent parameter ox, instead of the usual linear relationship, a rather unusual graph is observed. Comment on this graph, providing the mechanism of any relevant rate-determining steps. 3.5 3- 25- log(kx) 2 1.5- 11 0.5 0 -0.5 0 0.5 1.5 OH + EtOH (5)

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6(e)
For acid-catalysed hydrolysis of substituted benzoic esters (in 99.9% H2SO4) the
rate-determining step follows protonation:
H*
ö-Et
H
O-Et
RDS
+ H₂O
+ H₂O
R
R
R
When rates are measured and their logarithms are plotted against the Hammett
substituent parameter ox, instead of the usual linear relationship, a rather unusual
graph is observed. Comment on this graph, providing the mechanism of any
relevant rate-determining steps.
3.5
3-
25-
log(kx)
2
1.5-
11
0.5
0
-0.5
0
0.5
1.5
OH
+ EtOH
(5)
Transcribed Image Text:6(e) For acid-catalysed hydrolysis of substituted benzoic esters (in 99.9% H2SO4) the rate-determining step follows protonation: H* ö-Et H O-Et RDS + H₂O + H₂O R R R When rates are measured and their logarithms are plotted against the Hammett substituent parameter ox, instead of the usual linear relationship, a rather unusual graph is observed. Comment on this graph, providing the mechanism of any relevant rate-determining steps. 3.5 3- 25- log(kx) 2 1.5- 11 0.5 0 -0.5 0 0.5 1.5 OH + EtOH (5)
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