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322bsu09_e1_key

322bsu09_e1_key - 1 Chemistry 322bL Name l g Basic Organic...

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Unformatted text preview: 1 Chemistry 322bL Name - l g Basic Organic Chemistry July 13,2009 TA Stick lgiilll EXAMINATION 1 Answer the following questions in the space provided. Please organize your thoughts and attempt to make your answer as legible as possible. lfwe cannot read your answer, it cannot be given credit. Please remember that C-C-C-C without hydrogens and “stick” structural representations will be given N0 credit (except for rings only). I (12)_________ ——-— e (26)______ 11 111 IV (16) V (10) VI (12) VII (12) TOTAL (100) Read each question carefully in its entirety. Check immediately for 9 (including this cover) different, non-blank pages in this document. Chemistry 322bL Examination 1 page 2 July 13, 2009 I. (12 pts) Provide names for the following structures, or structures for the following names, as appropriate. Either IUPAC or common names are acceptable. lS—OH \\ . ‘ Q/ 0 V1Z l t i O s (e) o-chlorobenzoic acid (f) 4-bromo—3-fluoroacetophenone Q 6 l‘ H U‘ m @kx/n F Chemistry 322bL Examination 1 page 3 July 13, 2009 II. (12 pts) Using the partial structures given, draw all additional reasonable resonance structures to complete a good representation for the structure of each of the following molecules. (Note: you may have more partial structures than you need!) (a) ,4? G 4 m <H> PC) a?) H @;[email protected] *" Q ._. i3? ._. i3? th ‘—> ”O «woe u Ct <5> ~00» (C) 5" / 65 / “£3“ 0' <3> H CH3 CH3H Chemistry 322bL Examination 1 page 4 July 13, 2009 III. (26 pts) Please fill in the blanks 9; the best answer for each of the following. (a) In the space provided, state whether each of the following molecules is aromatic, anti-aromatic or non-aromatic. CH3C H3 (06$ O .060 QHH arm _an:l‘i_ 9mm _Klofl___m_9£flr_tmi (b) List the three criteria of the Hfickel rule regarding part (a) above. (The third has two parts.) i. K “A9 _ __ <H>ii Wm mob c amoral? C (c) lt‘any one criterion in part (b) is not met, the compound is classified as (d) Circle the two most common types of electronic transition observed in the ultraviolet-visible spectra of organic molecules. (Circle only two.) <2> n——>n* n——>n* O'-->O' \_. (L does not Exist ) Ft ‘ (e) Which transition in part (d) is always at longer wavelength if the molecule exhibits both? <1» n _ A)” at (i) Number the following molecules according to their rate of reduction by LiAlH4 in ether relative to one another. (Fastest is l, slowest is 4). Chemistry 322hL Examination 1 page 5 July 13, 2009 (g) Circle all of the structures below tha resent valid 1: molecular orbitals (bonding, nonbonding, or antibonding) for a pentad .- u {I ent species (radical, anion, or cation). (Ignore the relative _si_ze_ of the contributing atomic bas1s orbitals. Light and dark lobes represent the “+” and “—” algebraic sign (not charge) of the atomic basis wave functions contributing to each MO.) W 31/ \%@Q\ Kg? is? man) 52%? 9/»! d‘\ H2 War/m: @(Q é/ ,6 (h) Which of the following is/2,normal, conventional way to represent the polarity of a a“) ' E2 carbonyl group? (Circle all that ap . . (i) Cyclohexyl iodide exhibits an absorption in its UV spectrum near 260 nm. What kind of < i1: transition must this be? (Hint: the carbon-iodide bond in Can—1 13 unusual] .. weak.) 7t—)7t* n—>n* o—m Chemistry 322bL Examination 1 page 6 July 13, 2009 (3) Which of the following compounds exhibits the longest wavelength km“ 1n its UV-Visible spectrum? firing“ (k) Which of the following IS the best Diels-Alder diene? IV. (16 pts) Give the organic products for the following reactions. Be sure to note product stereochemistry and/or regiochemistry wherever relevant. You need not balance the equation, show byproducts, or show any mechanism. “Workup” means treatment with water or dilute aqueous acid followed by isolation of the product by appropriate means. (a) o H C\ ' OCH3 1)LiAlH4,Et20 /\ CHIS” j a/rqém-e, <Z> ‘ 2) workup (kl M 04 ‘CH3 éHCH‘g 7 :0 OH (b) E \OCHa / (0.1043 1% <7_> Q/ 1) NaBH4, MeOH [\‘D/ ,C 2) workup (LC’QC‘O'I 0/ \CH3 C‘JJCH?) é/a_ ~ OH l <1> Vg‘OCI-b + CH30H2MgBr ”320 y? 041C143 excess 2) workup Chemistry 322bL Examination 1 page 7 July 13, 2009 <Z> H 0% \C¢CH2 + I o CHzClz 2 room temp. CH3 “ (e) O f‘ CH3 + peroxides 4: _— er \ / \ <H> 0 (fr ——-——~ 4, j o, 1 ac [e CH3 CH3 ‘ @t‘ lipr (f) 0014 i l ., , C MOW +Br2 a CLEO-)«Cl-Ja-CH_CM-CHj < H H3 (1 equivalent) ‘20 C (ignore stereochemistry) Jr > ’L-(QL ,6 r ‘BV‘ 045(1an ~U4 =CH-CH5 V. (10 pts) Provide a reasonable synthesis (i. e., minimum number of steps, good yields, good regiochemistry, etc.) for the molecule specified below from the indicated starting materials and any other needed organic or inorganic reagents. Be as specific as you can regarding reagents and conditions. Show the product formed fiom each important step of your synthesis. OH H H2004) H10 Aéo and ~_____~’_ l\/' [I g Q 0" (WMWN § 60" /\ NBS Ccm'u /\..er ’ \_. Chemistry 322bL Examination 1 page 8 July 13, 2009 VI. ( 12 pts) Please answer the following with the fewest possible words in the space provided ‘ (a) Is there a problem with this resonance hybrid? If so, briefly explain. QESMW W <2> I H[+N\ occur W wigs o o constrain “\‘e‘x N (OWL pain M Pen Qro a bond 5 ice Qb°'ap(>ari. Overlap 4}); (AmL 96.33}th (b) Name three general empirical properties of aromatic molecules that differ from those of, say, cyclohexene. i' \IQM’3 \Qh) (‘EOC'i' l‘V 1%7’ ' <3> ii. guimjr Animist) MW 4/me QM ci‘élfl iii. specie/Q Wermodgmmic 3+4 El it +\{ (c) The heat of hydrogenation is measured for one mole of butadiene and for two moles of 1-butene. The two values are ~254 and —239 kJ/mole. Which value goes with which compound, and, in as few words a possible, what is(are) the origin(s) of this difference? Q//\/ =37 -~2’S‘-l QR (l)5()2“5’()2 C—C {condo (3) N =7 -—23<3123 VMWQLW (”Q/Wham! overlap resonance (d) It is said that the resonance energy of benzene is approximame 150 kJ/mole. What is the meaning of this resonance energy? Ewing benzem does mo‘l‘ have compared 13 04> eom a Hirer; localize—drvnow Why can’t itbemeasured more precisely? Th ‘01!” {zQA WOM in :Hd'fit’lmé 0‘44 90 fii Mnmo+ be WM expem Mania“) Chemistry 322bL Examination 1 page 9 July 13, 2009 VII. (12 pts) Addition of anhydrous hydrogen bromide to butadiene illustrates some very general and important concepts in organic reactivity. Below are some experimental observations regarding this reaction. Br / + \ ~80°C JV /\220//\Br / 78% ° N + HBr £4000 Br 4% \ / + /\/\Br 19% 81% Using the partial reaction coordinate diagram below, concisely explain why the product ratios are different under different conditions. Complete the diagram, adding curves if needed, and label the species at each energy minimum including a complete representation for any intermediate(s). Explain the relative stability of the two products. ‘ .. al ~30; reaciion la irreversible; «- Waugh am HMQ‘HCa“; CowimifegQ-C’Igjmm gnaw prz \omwzn (Ea, :7 .5 Armin ‘ . '0)’ HQ“ from Cam M~iomie if: Might M W 110’ From eguilibrm:@ W M fimfil flzrmodgmawiic Cohiroi ...
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