Chemistry 303 Second Examination November 14th, 1994 7:00 pm-9:00 pm Nine KEY Lab TA name, This is an open book test. You may use anything that is not alive. ‘Write all of your answers in the space beneath each question. If you mess up the assigned space, you may choose another space of equivalent size (e-g., on the back of a page) but itis your obligation to make clear where the answer is you wish graded. ‘Tum in this exam and no other material at 9:00 pm. READ EACH QUESTION CAREFULLY AND COMPLETELY. ANSWER ONLY WHAT IS ASKED! ‘THIS EXAM HAS SEVEN PAGES; Please check immediately to be sure you have a complete copy. THERE IS ALSO A SET OF "DATA SHEETS", primarily spectral data for your reference (5 PAGES). DO NOT TURN IN THE DATA SHEETS As always, there is opportunity for substantial partial credit without a complete answer-write something! If you do not have an answer to an early part of the question, just proceed and answer the rest in general terms as best you can, Good luck! Grade: Bie Oe bs ome 16. total score: Pledge:1. (25 pts). Using the empirical formula indicated at each part, propose one (perhaps different) structure which best fits the description for each of the following statements. No formal charge nor unpaired electrons allowed. In each case, explain your thinking in words and pictures (mechanism), A. CeH2 alkene most reactive toward Br. | Maximize Alkyl Groups on T bond Alkyl qroops stabilized C. C5H;O carbonyl compound with C=O stretch at lowest wavenumber. eorty Cag) streak waked Wp conjugating D4 t Hore resonauce structures, with Go siagle bowl. - eat: he, 2.1 bonds. Bet Rae hare Sig rte) & Q ? . Less gosh: pRA& [eae 1-bend} nl Fb ok a D. CsH,0 (n = any integer) most deshielded H (indicate which H in your structure). [Behe Induced nnqwretic Field i} Zaki) or auy alder eee ae ae, ee! 6 Wy region of Aldehyde — a strug Hanlon yyy E. CsHpO (n = any integer) ns absorption at longest wavelength. Pore corjagatiin => highest 7 i higher loyet 1% % lower: ae Cap between sad 1* Recteases cod conjeg at 5 Smidler gap > rhvilley AE fr excttahony smaller pa ae r= ete larger A.Il, (32 pts). Consider the Data Sheets, pp. 2-5. ‘These concern a laboratory problem in which a bottle of compound A was found without a label. The Orgo detective did a litle chemistry and spectroscopy. She found that compound A reacted with ozone (reductive processing) to give two compounds (B and C) which ‘were separated and their structures were determined by IR, NMR, and Mass spectra. Compound A reacted with HCl in ether solution to give one compound, D. HCL a0; =~ —— |B} +/C P] b. reduction E}-[] ‘A. Consider the spectral data and write the best structure for C. 7 1. Are the parent ion mass and relative intensity of the Cc < (b) 6 GMO = tw 72 4 Catbons D 452 23, oz 11% wiherp| NounS Aner. fea je molecule having Qe & 1 IXGI2)= 4B Probabid, A owe olecule 9 oe “0 2. Specify one feature of the IR spectrum for C which is especially consistent with the assigned structure. ea sd M25 cui) x x0 & typical of Av vaporturted Con- Be Ky Za ‘extent of reaction Th tmasibon stoke reser eee, ar olap solvent An stabilized | solvent ae teawettion state by t-bondany to the BYP forming And Aipole = stabilization of the bromoniuna Pes yan), No zpecial edt on (icactansts, so beset is hucr oF VI. (7 pis). Write the best mechanism which rationalizes the following reaction. Y higher nate [ue : HBr | ZB ee —— \ polar } Ge Be \ u-8r \ # ‘ RQ Keachin & Hid Luverabk by close eS preximity of second ays a “ites ath, fiokp ; than Br trapping