Question

an OH OH OH OH ОН Experiment Figure 2. Potential Alcohols and Carboxylic Acids You've recently begun internship at a company that makes fragrances for the food industry. The он OH date is April 1st, and you're nervous as Ethanol Propanol Allyl alcohol Isobutaol you are hoping that you can turn your internship into a job upon graduation! As soon as you arrive, you hear your OH name called out over the intercom with Propanoic Butyric Isobutyric the message to "quickly proceed to the 4-Pentenoic Acid Acid Acid Acid fragrance development lab, there's an emergency!" As soon as you arrive, your new manager exclaims she's glad you've arrived! Someone pulled an April Fools joke on her, and scrambled all of the labels on a bunch of the chemicals. She needs to know which is which so that they can be used as standards for QA (quality assurance) on the finished products. She then notices that the finished products are also missing! Your job is to take two of the unknowns, prepare the ester product, and then determine the identity so that your manager can begin using the compounds in QA. Prelab Questions 1) Fill in the reagent table in your notebook. NOTE: You will be unable to finish the table until you know the identity of your unknowns, so only fill in what you can before lab and then complete the table after Figure 3. Generic Scheme for Fischer Esterification lab. R-OH cat. H2SO4 Neat 120°C, 1.5h -он + R R OH

¹H NMR, ¹³C NMR, and GC-MS of Product between B + G:

Unknown B is a carboxylic acid, and Unknown G is an alcohol. The product of the two unknowns produced the ¹H NMR, ¹³C NMR, and GC-MS data shown. Of the carboxylic acids and alcohols shown in Figure 2, what are the identities of Unknowns B and G? What is the identity of the product formed by the two unknowns? Please explain how you found the answer.

Thank you!