Chem 2211 Exam IV Key - J 2 CHEWHSTRY 2'21 EXAM 4 April 22...

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Unformatted text preview: J 2'- CHEWHSTRY 2'21] EXAM 4 April 22, zoos Be sure to read each quesdon cerefidly. Partial credit will be assigned where appropriate. To receive filll credit you must answer the question completely. Relax and good lucid! 1. I. {6 pt_s}'Provide the proper IUPAC names for the following-compounds in the spaces provided: 2. Br CHE 3' J..- 1 H ‘ é " a (ease as ‘5’F5mmarb-LH0F0 4 7-dif'wth I- w 4. Cl [BE (Fm- LL hrJIH'E-HA-Jmiir E .5 MR] 2. (ii pis} Assign the appropriate designation at either Re o'rSi to the top [above the plane ofthc page} and bottom (below thepiane of the page) faces of the pro-chiral carbon in the following molecule. Inaddition, assign the designation of Pro~R or It}. Pro-S- to each of the indicated hydrogens in the same structure. Write your answers in the appropriate spaces presided below: 11. l— P re P'rc'e 3- H Total: lea Fees: _- Bottom Face: 3. [6 pts) Draw the appropriate structures for the lUi'AC names provided below: [4R,5S,”iS)4tErt—hutyi-5niodowlfl-dijneth ylnonone: 4. (6 pt's) Identify the relationship between the following pairs of compounds as: enantiomers; diastereomers, or identical compounds. Write each appropriate designation in the boxes provided: 9H UH CHs Ci \I/s:\‘r:/OH :3ch Br&/fl DHC/gxf’fma EHQ 0H CHO fir s; 3 mom 1 mos Home“ m5 GHC!‘ i PEG-balk] Ham-I o "F'CHEWa 5. {it}. pts') flr'aw the pmfluiztfs) that w'nuid. he- ahtained from the monuchlurinstihn- uf 2,3,3-Tnmethyl‘pantana. Y n‘mnnflt - ' ' ' 'fi. {12 pts) Provide all the pdssibie products from the reaction of Hmp‘rnpyl—S— | methyicyclqpe'ntene with DIP-Silly. Yum must also draw the reactive intermediate th'at ' leads to each ufthe Ero'ducts. Enclfise theintermefliates in their own individual hrackflsaud than draw an arrow to the appmpriate graduct. You'ara not reguir‘ed ti} indicate s‘teréuchemis EIZ or RIS in huranswer' s : T. {11 pts) Provide all of thepredncts, consistent with Markovn‘ikofis rule, resulting from the addition of one equivalent of HBr to the following compound: In order to receive full credit for this problem, you must provide the structure of each final product as well as the structure ofthe specific intermediate that leads to each product. In addition, clear] label the ma‘or kinetic and thermod -al'nic rodu'ets alou with the minor kinetic and thermad ami'c roduc'ts. He clear and organized in the arrangement of your answers. You do not need to"'show'stereochemistrv' fZ-or RES in our answer 3 . BF w : l {VI ms? k('..t+~. c, Paced- C'B % /L\/\f;r \:—L Mmsr {karmaéynahm Predefi- {5r Meier“ KEMHL. Free 6% ol- .3. [it] pt's) Assignthe appropriate R aunts fiesignations to each of the filliIflIity centers found in the following compounds. You must clear! indicate our answer for each | chiral center. Be careful and make sure to double check your work. g]. I... t .' HaG'IéHon ETHCHZCHI 1. Ham—EEC gm 1-5pm E/wanmtma}; EHECHE 2 momma EB 9. {3 pts) Cumpletethe feliuwing reaction schemes by adding the appropriate reegentis} andfiur predueflsj. Make sure to indicate the proper regieehemishjr. and stereaehemisn-y it‘ necessary: 5&3” or Pynem 0H A—h E1her Prat-M flr' glam? ML:- \‘ Ir ELI-tr: ache/H '1 5 4"} [Dally one Pméuoa It]. (It'll pts] Complete the renewing Diets-Alder reaction sehemes by providing either the apprepriate dienefdienephjle starting materials ”er-all pesgibte reaetien pretiuetlzs'). Shaw specific steremueliemistr}r when appropriate: 11. (12 pte} Draw all of the products formed in the following reactions. Make sure to indieate the proper regioehemistr},r and atereoehe'miatry when necessary. In addition, indieate whether the productll or product mixture, is optrieaii},r active by writing either YES or N0 in the box provided: Is this prodhotiproduot mixture optioatly active {yes or no J? Has '30:” a + man-12mg}: )k/ 5021+ [weenie mlxtum} ...
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