chem-3332TestIIA_Key - A Nehenclature 9 points 3 points...

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Unformatted text preview: A; Nehenclature: 9 points, 3 points each Please provide an a‘cceptabie name for each of the foilowing compounds. Be sure to indicate the jereochemistry wh ere appropriate. \n-v‘ OQ-‘CTH O | n 9"- U-bromo 3H1“) 4/, 0x0 «- hexana! 1. CH3-CH-CH—CH2-C-CH20H3 :2 {3: °~ 9,- 1: 5 a. B. Fact; (total 18 points, 3 points each) 1. Rank the foilowing compounds in order of their decreasing relative reactivity with + . _ - E (1 = most reactrve, 3 = least reabtwe): Cl // II 6* $ 2. Circle the compound which will NOT undergo Friedel Crafi’s reaction. OCH3 1 CE M ///m 1/ CN (05 r e 3. Circle the INCORRECT resonance structure in the bromination of anis‘ole with Brgf Br F6BI'3. ' "‘\ CH3 II Br /-' K. / @OCHg x. "a. _/ 4. Circle the reaction or series of reactions which will NOT lead to 1,3—gyclohexadiene. a) Acid-catalyzed isomerization of 1,4-cyclohexadiene. b) Reaction of cyclohexene with NBS, followed by KOH/CH3CH20H. c) Reaction of 1,3«butadiene with acetylene. 5. For the following molecules (assume [12]annulene is planar), classify each as aromatic, antiaromatic or non-aromatic (please write in the box provided for each). i - w (I) A?» ' ir‘lgtlo Ua/ SPé' 6‘ Classify the following molecules 01' ions as aromatic, antiaromatic or non-aromatic (please write in the box provided for each). ' / H Lila hi: 9 .. El .. H :00 N\ l l. L”; M/ \:::,/_ H EEG/Bxfi/BKH [(n%1:6 IE llnF-ll C. Fieactiions (5 points each problem; 30 points totai) Please provide 'ihe major product, or necessary reagents, or starting material in the box provided below. Be sure your drawing indicates stereochemistry if applicabie. ‘ 1. 0 cs \ \ ._.._._..—._..——-——-_v—-b- oer-«r3 a \ ,x/ % 06H} 2. ft . Prng (aw-fin} OH :1) ZnLHSE/Hfl/W OCH3 0 Li) BrCiJg cram > 1-KMnO4, cm A -' (fl-H- . r 3. 80012 _ ’7’ ‘ 1‘1 4. Li+'$iH(O-i—Bu)3 - v 0 Q N i ’J I”, c-OH 0— )7 3 - @545 we a?“ if“ ‘ [:1 cm Li El 1. Na or NaOH { 39 <3 ’\ ‘*“‘ 2 \ Br // ' \ / 2 l.- W (EV V: \ ' 3.012m1013 30‘!“ . b C'HJ'EW U + (I Q @Owgfl f 6. Q \X E)” Brz / hV , _ i / 2. NaCN (Na+ HCEN) ' / J \ f 8. CHSMgBr / ether \ U a ‘4'. _-"I: I Er ,. ‘ D. Mechanisms: ‘(10 pts each) Provide clear mechanisms for reactions 1 and 2. Use curved arrow notation to indicate'electron flow". Show alt intermediates and all formal charges. If there is w more than one resonance structure, you must show the "best" (Le. lowest energy) structure. t. . g" “raimhbn O AAdhon/Etr : O ‘CHséNa. 0 / CHSOH o - r: o J, . if” 0 ‘ f 1 1L é~> 1 ('9 r L. '3 I \t’ o 0545 Q J (5 EL D OH CHECE E. Synthé‘sis: 13 points Outline an efficient synthesis for the molecule shown below using any of the following reagents: alcohol, alkene, and/or alkynes of two carbons or less, benzene, and any inorganic reagents, any oxidizing or reducing agents and any peroxy acid. F. Spectroscopy, 10 points A Compound with the'formula CQH1002 exhibits the IR, 1H NMR and 130 NMR (proton spin decoupled) vectra shown on the following page. Please identify the compound and draw the structure in the box provided below. 1172 1359 J'TT‘T r-I'"TJ .T-rr-rn'y-x Ij-T-x-r a Frown NMR 3’ 5 5 “1":- “"- 3% El U WW ITTnITI‘FLflrT'an_m1,I:WITTtF1TTTT7T-fl1'rlfli.77Hiafil1iprfiIWI—rwfirjr-rw—‘J—g—I—r-‘r—I—fi 290 15-0 Carbon 13 bfi-fl 160 120 - 100 an 50 40 20W 10 ...
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