SS11 Final - Exam answer key PDF

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CHE 321 Summer 2011

Final Exam

Form 2

Multiple Choice Questions: 100 points 1. Choose the major product of the following reaction.

2. Choose the order that has the following conformers of ( S)-2,3-dimethylpentane correctly arranged with respect to increasing stability.

3. Select the major product of the following reaction.

CHE 321 Summer 2011

Final Exam

Form 2

4. Select the major product of the following reaction.

5. Choose the major products of the following reaction.

A. i + ii

B. i + iii

C. ii + iv

D. iii + iv

E. All of them

6. Choose the correct intermediate formed based on the following curved arrows.

CHE 321 Summer 2011

Final Exam

Form 2

7. Select the incorrect statement about Amoxicillin, an important antibiotic for the treatment of diseases such as pneumonia.

A. The atom marked (a) is an sp2 hybridized oxygen atom. B. The bond marked (b) is shorter than the bond marked (d). C. The nitrogen atom marked (c) contains one lone pair of electrons. D. Amoxicillin contains two amide functional groups. E. Amoxicillin contains five chirality centers.

8. Choose the structure that is not a resonance structure of X.

CHE 321 Summer 2011

Final Exam

Form 2

9. Select the most stable anion below.

10. Select the reaction that leads to the incorrect major product.

11. Choose the answer that best describes the molecular shape of ozone, O3. A. linear

B. bent

C. tetrahedral

D. trigonal pyramidal

E. trigonal planar

12. Choose the order that has the following correctly arranged with respect to increasing solubility in water.

CHE 321 Summer 2011

Final Exam

Form 2

13. Choose the major product formed from the following E2 reaction.

14. Select the method(s) that would give 3-methyl-3-hexanol as the major product.

A. i

B. ii

C. i + ii

D. i + iii

E. All of them

CHE 321 Summer 2011

Final Exam

Form 2

15. Select the incorrect statement concerning the two reactions shown below.

A. In both reactions, NaN3 acts as a nucleophile. B. If the solvent was changed to water, the rate of reaction (1) would decrease. C. The rate of reaction (1) is dependent on both the alkyl bromide and NaN3. D. The rate of reaction (1) is faster than the rate of reaction (2) because the alkyl bromide in reaction (1) is less stable than the alkyl bromide in reaction (2). E. If ethoxide was used instead of NaN3 in reaction (2), the major product would then be 2methylpropene.

16. Choose the correct relationship between the pair of structures shown below.

A. constitutional isomers

B. diastereomers

D. identical

17. Select the major product of the following reaction.

C. enantiomers

E. resonance structures

CHE 321 Summer 2011

Final Exam

Form 2

18. Choose the most stable conformation of the major product of the following reaction.

19. Choose the order that has the following compounds correctly arranged with respect to increasing acidity.

20. Select the correct structure for (R,E)-pent-3-en-2-ol.

CHE 321 Summer 2011

Final Exam

Form 2

Short Answer Questions: 80 points 21. Give the structure of the major product of the following reaction. Use wedged or dashed bonds if appropriate. 5 pts

22. Give the structure of the major product of the following reaction. Use wedged or dashed bonds if appropriate. 5 pts

23. Give the structure of the major product of the following reaction sequence. Use wedged or dashed bonds if appropriate. 8 pts

24. Using the curved arrow formalism, show all the bond making and bond breaking steps of this reaction. 10 pts

CHE 321 Summer 2011

Final Exam

Form 2

25. Propose a synthesis of dihydrotagetone, one of the primary odorants in the marigold plants, starting from any compound(s) containing four carbon atoms or less. 10 pts

26. Using the curved arrow formalism, show all the bond making and bond breaking steps of this reaction. Your mechanism must account for the stereochemistry of the product. 10 pts

27. Propose a synthesis of (Z)-hept-5-en-1-ol starting from 4-bromobutanal. You may use any other compound. 12 pts

CHE 321 Summer 2011

Final Exam

Form 2

28. Based on the information given below, determine and clearly draw the structures of compounds A, B, C, D, E and F. All six compounds are distinct. Compounds B and C are meso compounds. Compound F is a racemic mixture. Use wedged or dashed bonds on compounds where appropriate. For compound F, you only need to give one enantiomer. 20 pts...