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EXAM 2 J - EXAM 2— Pal 200 thm333 A NOMENCLATURE(12...

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Unformatted text preview: EXAM 2—! Pal! 200; thm333\ A. NOMENCLATURE: (12 points, 4 pts. each) 9600 ' H Give an acceptable IUPAC name for each of the following compounds. Be sure to indicate the stereochemistry where appropriate. CHZCH3 Br CH3 H30 Br c2H20Hch3 B. Facts: Total = 34 points 1. Place the following radicals in order of increasing stability (1=least stable, 3=most stable). (3 pts.) D D D 2. Place the following halides In order of their Increasing reactivity In the E2 process (1=least reactive 3=most reactive). (3 (pts.) or: 5; D D D 3. Place the following halides in order of their increasing reactivity in the 8N2 process (1=Ieast reactive, 3=most reactive). (3 pts.) m D D D Cl Cl 4. Label the pairs of molecules as identical, enantiomers, diastereomers, or structural isomers. (6 pts.) CH3 a. Br + CH CHO CHO H OH b‘ Br H Br H CHQOH EHQNHg H\ 5 40H | C. H V 9 ‘ Br EH3 CHO HO +CH3 Br CHZOH HO H CHO S E E 5. Label each molecule as chiral or achiral. Star (3,6) any chiral carbon atoms. (9 pts.) Cl 6. Sketch the reaction-energy diagram of a reaction having the following characteristics: a. three step process: A + B —-> C —-> D -—> E (product) b. The first step is endothermic and the rate determining step. c. The second and third steps are exothermic. d. The third step is faster than the second step. e. The overall process is exothermic. Label both axes, the positions of any transition states (T S1, etc.), and the positions ofA - E. (1 0 pts.) C. REACTIONS (32 pts) For each of the following reactions or series of reactions, draw the final major organic product, or reactant in the box. Give only one structure per box. Be sure to indicate STEREOCHEMISTRY where pertinent. In multiple step reactions, you may place intermediate products below the reaction for partial c 1) 2) 1) NBS (1 equivalent), light 2) NaSH 3) CH3OH redit. CH 3 Nal + NaBr acetone l 6) Na OCH3 D. Mechanism: 10 points The following reaction yields a mixture of products. Provide a clear mechanism for the formation of A , B and C. Use curved arrow notation to indicate "electron flow," and show all intermediates and formal charges. Br I OCHQCHa CHSCH20 Ht?!C CHCH3 CF3CH10H H3C CHgCHg heat + A B + CH3CH20 H3C CH3 C E. SYNTHESIS (12 points) From cyclohexane and any inorganic reagents, synthesize the compound below. H00 ...
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