Hydrolysis and Formation of EstersWinthrop University Organic Chemistry Lab IIDepartment of Chemistry CHEM 304Hydrolysis and Formation of EstersEsters, like most carboxylic acid derivatives, typically undergo acyl substitution reactionswhen treated with nucleophiles under acidic conditions. When water is the nucleophile,the reaction is called a hydrolysis. In this experiment, an ester (aspirin) will behydrolyzed to produce salicylic acid. This carboxylic acid will then be reacted with acidicmethanol to produce a methyl ester (methyl salicylate) via Fischer esterification. Thisester is used commercially as a flavoring and is known as oil of wintergreen.OOHOCH3OOHOHOOHOCH3OH2OH2SO4CH3OHH2SO4Safety:Sulfuric acid is a strong acid and can cause severe burns and damage to eyes.Dichloromethane is a suspected carcinogen.Procedure:Hydrolysis: Crush and weigh 3 tablets of aspirin. Place the aspirin in a 5 mL conical vialwith a spin vane. Add 2.5 mL of water and 0.3 mL of sulfuric acid to the flask. Attach acondenser and reflux the mixture with stirring for 20 minutes. Allow the flask to cool toroom temperature and transfer the mixture into a 30 mL beaker. Add 5 mL of cold waterand break up the solid mass into fine crystals. Collect the solid by vacuum filtration usinga Hirsch funnel. Wash the solid with 5 mL of cold water, and press them down with aspatula. Allow the vacuum to pull for at least 10 minutes to help dry the solid. It is crucialthat the solid be thoroughly dry before the next reaction. Determine the mass and meltingpoint of the solid hydrolysis product.Esterification: Place the hydrolysis product into a 5 mL conical vial with a spin vane. Add2.5 mL of methanol and 0.3 mL of sulfuric acid to the flask. Attach a condenser, andreflux the mixture with stirring for 1 hour. Allow the flask to cool and transfer thecontents to a small separatory funnel. Add 5 mL of saturated sodium bicarbonate andextract the mixture with two 5 mL portions of dichloromethane. Place the combinedlower organic layers back into the separatory funnel and wash with 5 mL of saturatedsodium bicarbonate. Drain the lower organic layer into a small Erlenmeyer flask and dryit for 5 minutes over a small amount of anhydrous sodium sulfate. Transfer the solution toa small pre-weighed beaker and evaporate the dichloromethane with gentle heating aidedWinthrop University Organic Chemistry Lab IIDepartment of Chemistry CHEM 304with a gentle air stream. Determine the mass of your product and obtain a 13C-NMRspectrum.Write-Up:Interpret your NMR spectrum and explain how you determined which peaks belonged towhich carbons. Calculate the percent yield for each reaction and an overall percent yieldfor the synthesis of methyl salicylate from aspirin (assume each tablet contained 325 mgof aspirin).Questions:1. From your data, calculate the percent of actual aspirin in an average aspirin tablet.2. Propose a “one pot” set of experimental conditions that will transform aspirin intomethyl salicylate (i.e. can be done in one flask all at once). 3. Design a synthesis of methyl salicylate starting from