“Fischer esterification and hydrolysis lab” Salicylic acid was mixed with methanol and H2SO4 (sulfuric acid). What are 2 purposes of using H2SO4 over another acid such as HCl or HOAc? “Fischer esterification and hydrolysis lab” Salicylic acid was mixed with methanol and H2SO4 (sulfuric acid). What are 2 purposes of using H2SO4 over another acid such as HCl or HOAc? Salicylic acid was mixed with methanol and H2SO4 (sulfuric acid). What are 2 purposes of using H2SO4 over another acid such as HCl or HOAc? Solution The esterification of salicylic acid (C 7 H 6 O 3 ) with methanol (CH 3 OH) is represented as C 7 H 6 O 3 + CH 3 OH <======> C 8 H 8 O 3 + H 2 O The Fischer esterification reaction is reversible in acid. Concentrated sulfuric acid is used as the acid catalyst in the reaction. The functions of concentration sulfuric acid (H 2 SO 4 ) are listed below. i) In the first step of the esterification reaction, the acid (salicylic acid) is protonated by conc. H 2 SO 4 . The protonated acid is the attacked by CH 3 OH to form the product (the reaction involves more than one step). Conc. H 2 SO 4 acts as the proton source in the reaction. ii) Dilute H 2 SO 4 or dilute HCl or acetic acid (CH 3 COOH) may also function as the proton source; however conc. H 2 SO 4 is preferably used because conc. H 2 SO 4 absorbs moisture. The equilibrium reaction proceeds to the right (product favored) when moisture (H 2 O) is removed from the system at equilibrium. Conc. H 2 SO 4 absorbs moisture from the system, thereby favoring the formation of methyl salicylate, C 8 H 8 O 3 . The other three acids cannot remove moisture from the system and hence, the yield of the product is low. .

1. “Fischer esterification and hydrolysis lab”
Salicylic acid was mixed with methanol and H2SO4 (sulfuric acid). What are 2 purposes of using
H2SO4 over another acid such as HCl or HOAc?
“Fischer esterification and hydrolysis lab”
Salicylic acid was mixed with methanol and H2SO4 (sulfuric acid). What are 2 purposes of using
H2SO4 over another acid such as HCl or HOAc?
Salicylic acid was mixed with methanol and H2SO4 (sulfuric acid). What are 2 purposes of using
H2SO4 over another acid such as HCl or HOAc?
Solution
The esterification of salicylic acid (C 7 H 6 O 3 ) with methanol (CH 3 OH) is represented as
C 7 H 6 O 3 + CH 3 OH <======> C 8 H 8 O 3 + H 2 O
The Fischer esterification reaction is reversible in acid. Concentrated sulfuric acid is used as the
acid catalyst in the reaction. The functions of concentration sulfuric acid (H 2 SO 4 ) are listed
below.
i) In the first step of the esterification reaction, the acid (salicylic acid) is protonated by conc. H 2
SO 4 . The protonated acid is the attacked by CH 3 OH to form the product (the reaction involves
more than one step). Conc. H 2 SO 4 acts as the proton source in the reaction.
ii) Dilute H 2 SO 4 or dilute HCl or acetic acid (CH 3 COOH) may also function as the proton
source; however conc. H 2 SO 4 is preferably used because conc. H 2 SO 4 absorbs moisture. The
equilibrium reaction proceeds to the right (product favored) when moisture (H 2 O) is removed
from the system at equilibrium. Conc. H 2 SO 4 absorbs moisture from the system, thereby
favoring the formation of methyl salicylate, C 8 H 8 O 3 . The other three acids cannot remove
moisture from the system and hence, the yield of the product is low.