CHEM 335 Final Exam Questions and Answers Latest Updated 2024/2025 (GRADED)

CHEM 335 Final Exam Questions and Answers Latest Updated 2024/2025 (GRADED) Write accurate structures for the following: a) a chiral allene b) 18-crown-6 c) the HOMO of 1,3,5-hexatriene d) benzyl isobutyl disulfide e) the hydrate of acetaldehyde 3. (15 points) Arrange the following in order with respect to the property indicated. Write MOST and LEAST under the compounds with the highest and lowest values, respectively. a) reactivity towards electrophilic substitution MIDDLE / / / LEAST / / / MOST 3/11 b) rate of HBr addition LEAST / / / MIDDLE / / / MOST c) polarity (amount of charge separation) of the bond LEAST / / / MIDDLE / / / MOST d) reactivity towards nucleophilic addition MOST / / / MIDDLE / / / LEAST e) rate of hydrolysis in aqueous acid MOST / / / MIDDLE / / / LEAST 4. (15 points) Complete each of the following reactions by writing the missing part: either the necessary reagents and conditions or the structure of the expected major product: a) b) 4/11 c) d) e) 5. (15 points) Complete each of the following reactions by writing the missing part: either the necessary reagents and conditions or the structure of the expected major product: a) b) c) d) 5/11 e) 6. (15 points) Write a complete mechanism for the reaction shown below. Show all steps, all resonance forms for intermediates, and all electron-pushing arrows. 7. (15 points) Write a complete mechanism for the reactions shown below. Show all steps and all resonance forms for intermediates. 6/11 8. (15 points) Write a complete mechanism for the acid-catalyzed hydrolysis shown below. Show all steps, all resonance forms for intermediates, and all electron-pushing arrows. Do NOT use H+ or -H+ ; use the appropriate acid or base. 9. (15 points) Complete the following synthetic sequence by adding the reagents and conditions necessary at each step. 7/11 10. (20 points) Show how to synthesize the following compounds. As the source of the carbons in the final product, you may begin with any alcohol having four or fewer carbons and benzene. a) 8/11 b) 9/11 11. (20 points) The chiral epoxide below adds methanol to form two different regioisomers, depending on the conditions used