Wilkes University Synthesis of Oil of Wintergreen Lab Report

Subject : Synthesis of Oil of Wintergreen.

I need full report see attached for lab manual and all Data Also, report form.

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1) Assess the effectiveness of the experiment and your technique by
A) reporting the yield of each step in grams and percent as well as the overall percent yield (What is “overall
percent yield”?). SHOW ALL CALCULATIONS!
B) Give a complete analysis of the identity and purity of your final product and any isolated intermediates.
2) What was the purpose of the addition of the 2M NaOH and the 6M HCl during the procedure for Part 1? As
part of your explanation, provide a chemical equation for each reaction.
3) Chemists sometimes add one reactant in excess relative to another limiting reactant to shift the equilibrium.
Recall Le Chatelier’s principle. What reactant was used in excess during the formation of salicylic acid
chloride, salicylic acid or thionyl chloride (transformation 2)? Show what happened to this excess reactant
by providing a balanced chemical reaction. Hint: The next reaction (transformation 3) involves the addition
of methanol and in addition to the desired methyl salicylate (oil of wintergreen) chloromethane (CH3Cl) is
also formed.
4) If methanol was not added to the salicylic acid chloride soon after its formation but instead the acid chloride
was allowed to sit for an indefinite period, a “dimerization” may occur. Draw the dimer and show
mechanistically how it forms.
5) The saponification (hydrolysis) of an ester results in the formation of a carboxylic acid and an alcohol. The
saponification of acetylsalicylic acid was carried out during this experiment. Draw the products of the
saponification reaction and circle the carboxylic acid and alcohol that were formed as a direct result of the
6) Draw the mechanism for the hydrolysis of Acetylsalicylic acid to Salicylic acid.
7) Provide the product of the follow reaction sequence:
H2O / NaOH

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