SS14 E1 key - Exam answer key PDF

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Form 1

CHE 321 Summer Exam 1

June 4, 2014

The first 10 questions are multiple choice questions, worth 5 points each, and should be answered by filling in the appropriate bubble for each question. Questions 11-18 are short answer questions with points indicated on the question. These questions should be answered in the space provided on the front and back of the answer form.

Page 1

Form 1

CHE 321 Summer Exam 1

June 4, 2014

Multiple Choice Questions: 50 points 1. Choose the order that has the following contributing structures of N,N-dimethylformamide correctly arranged with respect to increasing importance (stability). (lecture 3, slide 4)

2. Choose the order that has the following compounds correctly arranged with respect to increasing solubility in water. (WS2 quiz, q5)

3. Choose the product formed from the following set of curved arrows. (lecture 1, slide 35).

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Form 1

CHE 321 Summer Exam 1

June 4, 2014

4. Select the structure that is not a contributing (resonance) structure of compound X. (lecture 2, slides 4 & 5)

Use the following structure of serotonin to solve the next two problems.

5. Select the correct molecular formula of serotonin. (lecture 1, slide 40) A. C9H12N2O

B. C10H12N2O

C. C9H13N2O

D. C10H14N2O

E. C9H15N2O

F. C10H16N2O

6. Choose the hybrid orbitals that are used to form the indicated bond on serotonin. (lecture 1, slide 63) A. Nsp-Csp3

B. Nsp2-Csp3

C. Nsp3-Csp3

D. Nsp-Csp2

E. Nsp2-Csp2

F. Nsp3-Csp2

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Form 1

CHE 321 Summer Exam 1

June 4, 2014

7. Select the acid-base reaction(s) that is(are) shown correctly, where the equilibrium lies to the right. (lecture 3, slide 46; WS3, q1-4)

A. I

B. II

C. III

D. I + II

E. I + III

F. II + III

8. Choose the order that has the following compounds correctly arranged with respect to increasing boiling point. (WS2 quiz, q6)

9. Select the molecule(s) that has(have) trigonal pyramidal geometry. (WS2 quiz, q2)

A. I

B. II

C. III

D. I + II

E. I + III

F. II + III

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Form 1

CHE 321 Summer Exam 1

June 4, 2014

10. Consider the following acid-base extraction procedure to separate compounds i, ii and iii. Select where compound ii would end up. (WS3 quiz, q10)

Short Answer Questions: 50 points 11. The following anion has several contributing (resonance) structures. Draw the best contributing structure of the following anion, showing all lone pairs and any formal charges. (WS1, q1) 5 pts

12. Draw the structure of the major product of the following acid-base reaction. (WS3 quiz, q7) 5 pts

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Form 1

CHE 321 Summer Exam 1

June 4, 2014

13. Draw the structure of the major product of the following deuterium isotope-exchange reaction. (WS3, q7; lecture 3 slide 51) 5 pts

14. Below is the hypothetical neutral structure of tyrosine, and a table with the pKa values of the -carboxylic acid, -amine, and side chain functional groups. Draw the most predominant structure of tyrosine in a solution with pH = 7.4, showing all lone pairs and any formal charges. (WS3, q5) 5 pts

-carboxylic acid (pKa)

-amino group (pKa)

Side chain (pKa)

2.2

9.1

10.1

15. Give the structure of one compound that meets all of the following criteria. (WS1, q4) 5 pts a. Has a molecular formula of C5H8O. b. Has exactly 4 sp3 hybridized carbon atoms and 1 sp2 hybridized carbon atom. c. Has a carbonyl (C=O) group.

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Form 1

CHE 321 Summer Exam 1

June 4, 2014

16. There are four amines with the formula C3H9N. Among these isomeric amines, draw the structure of the amine does not exhibit intermolecular hydrogen bonding. (WS2 quiz, q9 + 10) 5 pts

17. Using the curved arrow formalism, show the bond breaking and bond making steps of the following reaction. (WS3, q6) 10 pts

18. Using the library of synthetic reactions on the cover page, propose a synthesis of the following compound from compounds containing four carbon atoms or less. (WS2, e) 10 pts

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