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Test_II_3331_C - I3‘Bl EW’W C“ A Nomenclature(12 pts...

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Unformatted text preview: I3‘Bl EW’W C“ ' A. Nomenclature: (12 pts). Give a IUPAC- name for each of the follow-ring compounds: (4 pts each.) {'I a) 0H3 H30 CH3 it?"- I H Br Br H CH20H3 B. Facts: (Total = 32 points) 1 Place the following carbanions in order of increasing stability (1 = least able 3: most stable) (6 pts.) U -~.._r- l: 5 2 Place the following alkyi halides in order of increasing reactivity in the SW process (1 2 least reactive 3: most reactive) (6 pts) BrU CH2CH3 OBI. CHQCHS O, C HgoHEBr E l a D _ e. Use the bond dissociation energy table at the end of the exam to calculate the AH" in kcal/mol for each of the following reactions. (You must show your calculations in the box provided under the reaction). Label each reaction as endothermic or exothermic in the box provided beside the reaction. (6 points) a. (CH3)30H + Brg —r (CH3)3CBr + HBr :1 b-CHsCHzBr + tho —»-- CH30H20H + HBrl | I 4- Label the 1cCHOWWQJ pairs 07 compounds 85 identical. structural isomers, enantiomers or diastereomers, (6 points) Eur” __________,__ _ W .2. H _ OH 51) cr—m—l—uer er_....|_H ' ' OH or ' 2H3 . EH3 _ HgN'FCLfl-IOH Brn—éa—NHE .- _ EHe : EH3 \ /Ci or , __ BrQ CH3 H30/ l/Br . - ; .: l 5. Draw at! stereoisomers of t, 2, 4—tribromocyciopentane. Place enantiomers next to each other and circle them. Assign each structure that you have drawn a number designation (1, 2, 3, etc). Identify one pair of diastereomers by placing the number designations in the box indicated. (example: If structures 1 and 2 are diastereomers, you would put 1 and 2 in the box.) Identity all meso compounds by placing the number designation in the box indicated. (8 points. Be careful. Points will be deducted for duplicate or incorrect structures.) ' -' C. REACTIONS (36 points or 6 points each) For each of the following reactions or series of reactions, draw the final major product in the box. Give- only one structure per box. Be sure to indicate the STEREOCHEMISTRY where. pertinent. 9 OC(_C‘H3)3FHGGCCH3‘}5 __.._..._._._.*.. heat 2?) Two step reaction (identify A and B) BIZ " A UV light NaOCH3 x H 0% A —'———> B h m; 3} .—_——| CH3 _ H Br N3} . I - - l »———m—_—)~ H30 H Sice‘kone 1 CHECHECHg i i _______J ______ W[ L—»-- ”2” 4) ./ NaCN H / W 55'; c9 J: em Br 5) CH3 i 9 OCECHsh - 'r . Br _ —_._.._...._>. H 3 e M333 ",4 heat ' : 4% . ._ i 6) 1--i0d0_-1-methy]C}-'elopentane heated in ethanol —, + + «: -.».. r. 'x‘ '---/=\'r:-..:. D. Mechanism: 10 points The following reaction affords a mixture of products. Provide a Clear mechanism for the- formation of products A and B. Use curved arrow notation to indicate “electron flow”, and show all intermediates and formal charge. CH3 CH3 “ H20 ——'—'——'—+ _ heat + m OH A B i j i M“ f." M“ Lag“: E. Synthesis: 10 points From 2-methyl pentane, propane, any inorganic reagents, and any bases, synthesize the followmfirfdfm Ax fwfim'fi?‘ v. figmw “i ...
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