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Q1. (4 points) The chemical structure of Paroxetine (Trade name: Paxil), a drug used to treat anxiety disorders, is shown below in the box. The stereoisomer used clinically has the conliguration (3S,4R). Which stereurepresentation depicts this configuration? Circle the structure of your choice. soat NH I Pood F. scate cote Q2. (4 points) Sorbitol is a sugar aleohol found in many fruits such as apples, strawherries, and prunes. in the body, it. is produced by enzymatic reduction of glucose. The configurations of the stereogenic centers in sorbitol are 23,3R,4R,5R. Which Fischer projection represents Sorbitol? Circle the structure of your choice. CH2OH CH2OH OH HO A OH OH HO XH ou OH/ OH OH H OH H-FOH CHAO CH2OH Sorbitol CILOM CH2OH H-TOH H OH CHAOH CH_OH Q3. (4 points) 2 How many sterevisomers are possible for 4-methyl-2-hexenc? Q4. (4 points) A3C The pKa of the morpholinium cation is 8.33. Which of the following Lowry-Brousted bases are strong enough to deprotonate the morpholinium cation? Circle the buses of your choice. Note: pKa of H2 H3O are respectively 40 and-1.74. Consult your class notes for any other noeded pKa values. You will losc I point for each incorrect answer accompanying the correct answer. o. o B + H-B N H H H morpholinium cation o NaOH H2O NaH NaCI H-C=CNa NaNHA H2C ONa 55 18 QS. (4 points) In the spacc provided neatly draw the product of this Lewis acid-base reaction and in the spaces provided label the reuctunts as Lewis acid and Lewis base as appropriate. Be sure to show any formal charges. + of lews acid tewishase Q6. (6 points) Based on reactions described in Chapters 2 and 7, in the spaces provided, neatly draw the structure of the expected organic products in the following sequence of reactions. o CH3CI IT NaOH OH Ibuprofen Q7. (12 points) Neatly draw the structure of the expected organic product of each reaction. The structure you draw must clearly display the stereochemistry of the product. 2 Br HSs a) Hi CHg + Na+-SH Hawey O. D: CH3 CH3 & b) CH2 + Nat-IC=N: N~C CEN? CI R in H c) H Br CH3 + H is 0: Nat CH3 H D

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