Part 1. Using curved arrows show the mechanism for the following  reactions. Your mechanism must show the formation of all products provided in the reaction. (Answer to this must be submitted with the work scanned and sent to Dr. Metz after the exam) Part 2. Which mechanism, SN2, SN1, E1, or E2, does this reaction proceed through? (Answers to these questions must be provided in the space below in order to receive credit – this question must be answered to receive credit Part 1) a.   b.

Identify the stronger acid between each pair of organic molecules. Using the ARIO rules to provide a brief 1-2 sentence response that explains how you arrived at this answer. (Final answers to this question must be included in the space below to receive credit) a.     b.   c.     d.

Identify the absolute configuration (R/S) for all chiral centers below. (Answers to this question needs to be provided in the space below in order to receive credit) a.   b.

Refer to the E2 reaction below.   The following reaction provides all possible products; however, the expected major alkene product for the following is not generated for this reaction and the less substituted alkene product is the observed major organic product generated.   Part 1. Explain why the expected Ziatsev product is not observed. (Answers to these questions must be provided in the space below in order to receive credit)

Review the structure for Norethisterone, a progestin medication, prescribed for hormone therapy. Identify the hybridization, molecular geometry, and bond angle for each atom circled below. (Final answers to this question must be included in the space below to receive credit – Note you do not need to copy the table over when providing final answers, but make sure your answers are clearly associated with the correct atom/color combination). Atom     Oxygen – Green  Hybridization   Molecular geometry   Bond angle   Carbon – Red Hybridization   Molecular geometry   Bond angle   Carbon – Black Hybridization   Molecular geometry   Bond angle  

Part 1. Draw the chair conformations for cis-1,4-dimethylcyclohexane and trans-1,4-dimethylcyclohexane.( There should be 2 chair structures provided per cyclohexane ring). Note: You do not need to attempt to draw these structures on Canvas. Drawings of each chair conformation will need to provided in the work sent to Dr. Metz Part 2. Rank the chair conformation stability, 1 being the most stable and 4 being the least stable conformation, if there is a tie state which conformations are of equal stability. (Answers to this question will need to be provided with the structures sent to Dr. Metz after the exam) Part 3. Which isomer of 1,4-dimethylcyclohexane, cis or trans, is associated with the most stable conformation? (Answers to this question needs to be provided in the space below in order to receive credit)

a. Refer to Question 5b – Which solvent, polar protic or polar aprotic, would you expect to be used to facilitate the reaction outlined in question 5b? (Answers to these questions must be provided in the space below in order to receive credit) b. Which reaction intermediate outlined in your mechanism for 5b does this choice of solvent help stabilize? (Answers to these questions must be provided in the space below in order to receive credit)

Designate each alkene as either the (cis or trans) OR (E or Z) isomer. (Answers to this question needs to be provided in the space below in order to receive credit) a.   b.

Determine if the following chemical bonds would be classified as polar covalent, nonpolar covalent, or ionic. If the bond is polar covalent identify the atoms with partial negative or partial positive charges. (Final answers to this question must be included in the space below to receive credit) a. C—H  b. C—N  c. Cl—Cl d. C—O 

Convert the following Lewis structures to bond-line structures.  Work for this answer needs to be provided completed on your scratch paper and sent in the work sent to Dr. Metz after the exam is completed.   Lewis Structure A. B. D.     D. E.