Chemistry Question

PRINT NAME: Exam 3 Chem 231 Practice Spring 2024 1) Explain why an amide is much less reactive to hydrolysis than an acid chloride (5 points): 2) The structure of 2,4-pentanedione is shown below. It exists in equilibrium with about 80% of its enol form. i) Draw the enol form to the right of the equilibrium arrow: (3 points) ii) State two features of the enol form that stabilize it compared to the enol form of a simple ketone or ester: (4 points) iii) Draw a mechanism for the conversion of the keto tautomer to the enol form in acid: (3 points) 3) Rank the following carbonyl compounds in order of acidity (1 = most acidic, 4 = least acidic): (5 points) 4) i) Fill in the reagents to complete the synthetic sequence below, and draw the final product in the box: (10 points) 5) A student attempted to alkylate acetone with NaOH and n-Butyl bromide but none of the expected product formed: i) Explain why the reaction did not work, and suggest two other products that could form in this reaction mixture instead (hint: consider NaOH both as a base and as a nucleophile): (7 points) ii) Suggest how you would change the reaction so that the desired product would form: (3 points) 6) i) Draw a mechanism for the aldol condensation shown below: ii) (10 points) An attempted crossed aldol with cyclopentanone and acetaldehyde gave a very low yield of the product shown: Explain why this reaction did not work well: (3 points) Suggest a different aldehyde that would be successful in a crossed aldol with cyclohexanone: (2 points) 6) Name the following compounds: (10 points) 7) Draw a mechanism and give the major product of the following intramolecular Claisen condensation (hint: the product contains a 6-membered ring): (10 points) 8) Shown below are reagents for a Michael addition reaction: i) Draw the expected conjugate addition product to the right of the arrow. ii) (4 points) Explain why cyclohexene would not participate in this reaction with diethyl malonate: (3 points) iii) Draw another alkene, containing a different functional group from the example above, that would be a good electrophile in a Michael addition: (3 points) 9) Rank the following nitrogen compounds in order of basicity (1 = most basic, 4 = least basic) (5 points) 10) Fill in the expected organic products for the following reactions (2 points each):