Write the mechanism for the acid catalyzed hydrolysis of methyl benzoate
1 answer:
Hydrolysis of Methyl Benzoate yields Benzoic Acid and Methanol. This reaction is also called as Tranesterification (reverse of esterification). Acid in this reaction protonates the carbonyl oxygen, resulting in increasing electrophillic character of carbonyl carbon. Water acts as a nucleophile and methoxide leaves as a good leaving group. Mechanism is shown below,
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Explanation:
According to the Henderson-Hasselbalch equation, the relation between pH and is as follows.
pH =
where, pH = 7.4 and = 7.21
As here, we can use the nearest to the desired pH.
So, 7.4 = 7.21 +
0.19 =
= 1.55
1 mM phosphate buffer means +
= 1 mM
Therefore, the two equations will be as follows.
= 1.55 ............. (1)
+
= 1 mM ........... (2)
Now, putting the value of from equation (1) into equation (2) as follows.
1.55 = 1 mM
2.55 = 1 mM
= 0.392 mM
Putting the value of in equation (1) we get the following.
0.392 mM + = 1 mM
= (1 - 0.392) mM
= 0.608 mM
Thus, we can conclude that concentration of the acid must be 0.608 mM.