Sierah C.

asked • 10/03/18

A student completed the synthesis of salicyclic acid just as we did in our laboratory activity. They used 2.925 g of methyl salicylate, 3.5 mL of 6.0 M NaOH, an

A student completed the synthesis of salicyclic acid just as we did in our laboratory activity. They used 2.925 g of methyl salicylate, 3.5 mL of 6.0 M NaOH, and 4.1 mL of 6.0 M HCl. They obtained 0.886 g of product.
 
Wwas the methyl salicylate (MS) or the sodium hydroxide (SH) the limiting reagent for the first step?


                 was the limiting reagent



What is the theoretical yield of salicylic acid in this experiment?


                 g of salicylic acid



What is the percent yield on this experiment?


                 %

1 Expert Answer

By:

Ishwar S.

Hello J.R.S and Sierah
 
The 2 main reactants in this reaction are methyl salicylate and NaOH, therefore, you would only need to determine which of these 2 reactants is the limiting reagent. However, you can still confirm how much HCl is used in the reaction.
 
NaOH will hydrolyze methyl salicylate (an ester) into its corresponding carboxylate salt (sodium salicylate) and methanol (CH3OH). NaOH is generally used in excess in order to completely hydrolyze the ester, but this can be confirmed from the calculations.
 
To the carboxylate salt, HCl is added to convert sodium salicylate into salicylic acid. Excess HCl is added not only for the conversion process, but also to neutralize any excess NaOH.
 
The 2 reactions can be written as:
 
C8H8O3 + NaOH --> C7H5O3- Na+ + CH3OH
 
C7H5O3- Na+ + HCl --> C7H6O3 + NaCl + H2O
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10/03/18

J.R. S.

tutor
I was under the impression that both the phenolic OH and the methyl ester reacted with NaOH and that's why I put 2 NaOH in the equation.  Is that not the case?  Also, I mistakenly used H2SO4 instead of HCl, so I believe there should be 2 HCl in the equation. 
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10/03/18

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