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Summer CHE 322 Final Exam August 14, 2020

This is a 150 point exam.

1. Which reactions / reaction sequences will give the same major product? (5 points)

A. 1 and 2 F. 3 and 4

B. 1 and 3 G. 1, 2, and 3

C. 1 and 4 H. 1, 2, and 4

D. 2 and 3 I. 1, 3, and 4

E. 2 and 4 J. 2, 3, and 4

2. Kiliani-Fischer synthesis of the following aldotetrose gives two possible aldopentoses. Select the aldopentose product from the first reaction that would give an achiral aldaric acid upon oxidation with HNO3. (5 points)

Summer CHE 322 Final Exam August 14, 2020

3. Classify the following mechanistic step. (5 points)

A. ligand association

B. ligand dissociation

C. oxidative addition

D. reductive elimination

E. ligand insertion

F. ligand deinsertion

4. Arrange the following carbocations in order of increasing stability by typing in the numbers underneath them. For example, an answer of 1234 would indicate that you think 1 is least stable and 4 is most stable (with 4 being more stable than 3 and so forth). (5 points)

5. Choose the major product of the following isomerization reaction that begins with a retro- aldol, followed by an aldol condensation. The carbonyl carbon of the reactant is radiolabeled with the C-14 isotope, denoted by an asterisk. (5 points)

Summer CHE 322 Final Exam August 14, 2020

Use the following chart to answer the next two problems.

6. Give the specific name of the following structure. (5 points)

7. Choose the correct statements concerning the disaccharide shown below. (5 points)

1. The disaccharide contains a -1,4 glycosidic bond.

2. The name of the enzyme that can hydrolyze this disaccharide is -glucosidase.

3. Hydrolysis of this disaccharide gives D-allose and D-glucose.

4. The disaccharide is a reducing sugar.

A. 1 and 2 F. 3 and 4

B. 1 and 3 G. 1, 2, and 3

C. 1 and 4 H. 1, 2, and 4

D. 2 and 3 I. 1, 3, and 4

E. 2 and 4 J. 2, 3, and 4

Summer CHE 322 Final Exam August 14, 2020

8. Which of the following is(are) aromatic? (5 points)

A. 1 only B. 2 only C. 3 only D. 1 and 2 E. 1 and 3 F. 2 and 3 G. 1, 2 and 3

9. Choose the major product of the following Diels-Alder reaction which produces a racemic

mixture. Each choice shows just one enantiomer of the racemic mixture. (5 points)

Summer CHE 322 Final Exam August 14, 2020

10. Which of the following intermediate structures is(are) not expected to form during the following hydrolysis reaction? Type the letter of the structure or structures that are not expected to form. For example, if you think structures A and B are not expected to form, then type: AB (5 points)

11. The following cycloaddition reaction is analogous to the Diels-Alder reaction. Choose the

two  molecular orbitals that will interact during the reaction. Type in the two letters. For example, if you think orbitals A and B interact, then type AB. (5 points)

12. Choose the correct Fischer projection of the open chain form of the following monosaccharide. (5 points)

Summer CHE 322 Final Exam August 14, 2020

13. Draw the major product of the following intramolecular reaction. (5 points)

14. Draw the major product of the following Hoffman elimination. (5 points)

15. Draw the thermodynamic product of the following reaction that utilizes deuterium labeled hydrochloric acid. (5 points)

16. Draw the major product of the following reaction sequence. (5 points)

Summer CHE 322 Final Exam August 14, 2020

17. Draw the major product of the following reaction. (5 points)

18. Draw the structure of the reactant of the following reaction. (5 points)

19. Determine and draw the reactant of the following reaction sequence. (5 points)

20. Determine and draw the structure of compound A only. (5 points)

Summer CHE 322 Final Exam August 14, 2020

21. Determine and draw the structures of compounds B and C. (10 points)

22. Determine and draw the structures of compounds D and E. (10 points)

23. Propose a curved arrow mechanism for the following reaction. (10 points)

24. Propose a curved arrow mechanism of the following isomerization reaction. (10 points)

Summer CHE 322 Final Exam August 14, 2020

25. Complete the following synthesis by selecting from the list of 10 reagents below. Each reagent (or set of reagents) is labeled as a letter. In the answer box, simply place the order of reagents used as uppercase letters. For example, if your synthesis involves using reagent A followed by B and then C, and then D, your answer would be: ABCD. (10 points)