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Fall 2002 KEY - EX A M 7— F4 1 1 2.00 Qhflm‘jggl A...

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Unformatted text preview: EX A M 7—! F4 1 1' 2.00; Qhflm‘jggl A. NOMENCLATURE: (12 points, 4 pts. each) 9% i H Give an acceptable IUPAC name for each of lhe following compounds. Be sure to indicate the stereochemistry where appropriate. 2. CH20H3 _ ‘ ' 3. Br CH3 “(is New - ihégk H30 Br CHQCHQCHS B. Facts: Total = 34 points 1. Place the following radicals in order of increasing stability (1 =Ieasi siable, 3=most stable). (3 pts.) E 2. Place the following halides in order ol their increasing reactivity in the E2 process (1 =least reactive. 3=most reacfive). (3 pets.) 6,0 Nor or .,%( E \\ . Cl. I w «A l « @ m :l’il ' 3. Place the following halides in order of their increasing reactivity in the 3.42 process (1=Ieast reactive. 3=mosl reactive}. (3 pts.) E IH‘V' 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 intennediate products below the reaction for partial credit. 1) r“ CH ‘- _ Nal S I _ l I acetone % T NaBr H I 2) JR 1.) NBS (1 equivalent), light g g 2) NaSH - v L__—_'J 7‘? Br {SH b“)? 3) O/CHS fl CH3CIH --l enm’rfom H3CHM‘ CH3 ' HHK/ (SJ/V Flaw 3 3 f or; 4) QOOCHS Hie] H3O _ H éHgCHg Br +. NET OCH3 4. Label the pairs of molecules as idemicai. enantiomers, diastereomers, or structural isomers. {6 pts.) $43 Q1; 0 H0 CH3 Eflar’l’lio me (3 (9 Br @- CHO CHQOH H OH Ho H ' b. ' 3' H H Br 5+ 1:” mal UL (a ( Br H H Br CHQOH CHO QHaNHz (3)42!er2 H x 6 AOH H k 54cm _ c. g I c \ HrL—Br Brig‘H Dragfeflomfig CH3 EH3 5. Label each molecule as chiral or achiral. Star (are any chiral carbon atoms. (9 pts.) W 6. Sketch the reaction-energy diagram of a reaction having the following characteristics: a. three step process: A + B —+ C -—-r- D —-r- E (product) is. 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 overaii process is exothermic. Label both axes, the positions of any transition states (T 81, etc), and the positions ofA — E. (10 pts.) some y —"—'———-———-—.— Qaaa'HQ/v F—'— . 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 indicatef'electrfl it??? and Show all iggrmediates and r} ‘armal charges. N: Viifibgtfi Er gem-We 5' { ‘ra‘r PWdLLC a... lluw' . CH CH O ‘ " 3 2 ————p CHQCHS H C a heat + 3 I r 3.x ‘ = + '1 : L F C(22- HC / “A. . [.3 3/ @i it CHsoHQO . \ J If E. SYNTHESIS (12 points) From cy'clohexane and any inorganic reagents, synthesize the compound below. ‘T‘ Hzo/a CD BK fl‘thc/ TNBS (“ /-"\\\\ (>2? V \ Naol'f v ...
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