The flavors and aromas of almost any fruit are primarily due to esters. In an experiment, an artificial fruit flavor is prepared using the Fischer esterification (reaction of an alcohol with a carboxylic acid in the presence of sulfuric acid catalyst). Why is sodium bicarbonate solution used in the workup of the reaction? What advantage does sodium bicarbonate have over sodium hydroxide solution?

Create balanced chemical reactions for the following reactions. Organic reactions should be written with the line-angle drawing of each structure. 1.  Reacting salicylic acid with acetic anhydride to form acetylsalicylic acid, with the use of sulfuric acid as a catalyst. 2. Water reacting with acetic anhydride to form acetic acid.

7. Draw a circle around the compound in each horizontal row with the greatest water solubility and draw a rectangle around the compound with the lowest solubility in water. 1-pentanol 1-hexanol 1-octanol methanol OH Но OH Но НО 8. Classify the alcohols below as 1° or 2º or 3º. OH HO HO OH

4. Assume that an esterification reaction is done using 0.10 moles of a carboxylic acid and 1.0 moles of an alcohol. What is the theoretical yield (in moles) for the reaction? (You can write a generic esterification reaction to help answer this question and recognize the limiting reagent.) 5. A student completes the reaction described in question 4 and obtains 5.3 g of the product (the product has a molecular mass of 74.0 g/mol). a) What is the actual yield (the moles of product obtained)? Show your calculation, including units. 5.3 g product X mol products b) Calculate the % yield for the reaction. Show your calculation, including units.

1. Esters can be formed by the condensation of a carboxylic acid with the hydroxyl group of an alcohol or phenol. a) Use structures to show the condensation of acetic acid (IUPAC: ethanoic acid) with the hydroxyl of cyclohexanol. b) Explain why 'condensation' is an appropriate name for this reaction. c) You'll synthesize the ester in aspirin by condensing the phenol group of salicylic acid not with acetic acid, but with acetic anhydride. Explain why the experiment calls for the use of an anhydride, rather than an acid.

1. The reactant (2-methyl-2-butanol) has a limited solubility in water at room temperature. 10.0 mL of 2-methyl-2-butanol will dissolve in ~ 80 mL of water. In this experiment, 10.0 mL of 2-methyl-2-butanol readily dissolved in 20 mL of 12 mol/L aqueous HCl. a. Why does this compound exhibit some solubility in water? Consider intermolecular forces and include a diagram to illustrate the relevant intermolecular forces. Why is it not completely miscible in water (in all proportions)?

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