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Stereochemistry 1. Assign R or S configuration to the chiral center in each of the following molecules. Draw their mirror images and assign R or S configuration. What's the relationship between original molecule and its mirror image? (10 pts) a. OH H H3C b. CH3 H CH2CH3 c. O H HO CH3 H OH CH2OH Alkyl Halides: Nucleophilic Substitution and Elimination product(s) of the following reactions. Explain why you choose the mechanism. (10 pts) Draw the most favorable mechanism among SN1, SN2, E1, and E2 and predict the major a. (5 pts) NaI CI b. (5 pts) HO Br Alkenes: Structure and Reactivity 1. Calculate the degree of unsaturation and draw one possible structure in the following formulas. (4 pts) a. C5H5NO2 b. C6H5NCIBr 2. Assign E or Z or cis or trans designation for the following alkenes. (6 pts) CH3CH2 H H CH2OH C C H CN Cl CO2H H3C CH2CH2CH3 CH2 HC CH2NH2 CH3 C CH3CH2 C CH2NH HC CH3 Alkenes: Reactions and Synthesis 1. Draw the mechanism and predict the product of the following reactions. Show the stereochemistry of the products. (10 pts) a. CH3 + Br-Br H b. CH3 1. Hg(OAc)2, H2O 2. NaBH4 H c. CH3 1. BH3 2. H2O2, OH H Alkynes 1. What products would you prepare a. by mercury catalyzed hydration and b. by hydroboration/oxidation of the following alkyne? Draw the mechanism and predict the products. (10 pts) a. b. Polar Covalent Bonds; Acids and Bases 1. Calculate the formal charges on the atoms for the following molecule. (3 pts) :O : :0: : O : CH3C - : O. : O : - - 2. Draw the all possible resonance structures of the following compounds. (7 pts) a. (3 pts) NH2 O: CH O OH b. (4 pts) NH2

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