322bsu07_e2_key

322bsu07_e2_key - Chemistry 322bL Name 2 QIJQ Cm PF S Basic...

Info icon This preview shows pages 1–8. Sign up to view the full content.

View Full Document Right Arrow Icon
Image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 2
Image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 4
Image of page 5

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 6
Image of page 7

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 8
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: Chemistry 322bL Name 2 ) QIJQ Cm PF S Basic Organic Chemistry July 16, 2007 EXAMINATION 2 < e Answer the following questions in the space provided. Please organize your tho ts and attempt to make your answer as legible as possible. If we 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 N 0 credit (except for rings only). I (18) II (20) 111 (24) IV (20) V (18) TOTAL (100) Chemistry 322bL Examination 2 page 2 July 16, 2007 I. (18 pts) Provide names for the following structures, or structures for the following names, as appropriate. Either IUPAC or common names are acceptable. Be sure to specify stereochemistry if 1t is shown Km CQ (0 “/OL'My/ - 3-[44xeufé-0he- (3)0 H chm o W /C.. (c) trans-2,3,S—trimethylcyclopent—Z—enecarbaldehyde (d) 3-acetyl-5-nitrophenol ‘+\ ¢O Du 0-5 I”../ H3 (’4) /' (H) CH9 OLN \ £04) Chemistry 322bL Examination 2 page 3 July 16, 2007 II. (20 pts) (a) Azulene has a significant dipole moment. There are actually many structures that can be written. Writejust 5 additional structures selected to clearly illustrate your brief, concise, short, and succinct explanation of the dipole moment. 37 <——> etcetera m RQSOWWC garmg’fiuv A—OWJ- -—' a Mm ¥ar anion (b) Complete the following partial structures so as to draw all reasonable resonance structures to complete a good representation for the indicated carbocation. There may be more partial structures than you need. (+ 23H2 (+)CH2C CH2C H2 “/1 ‘ H2 N \ CI H NC NC N02 N02 OCH3NO OCH3NO OCH3 OCH3 H2 H2 Cl H2N 1 CI $® H No2 NC No2 l OCH3 00 H3 G) Chemistry 322bL Examination 2 page 4 July 16, 2007 (c) In the space provided, state whether each of the following molecules is aromatic, anti-aromatic or non-aromatic. 3 CH CH3CH3 CH3 I. 3 - ' \/)N(+ (23‘1“: O © 0 C) ©Qtowi’ric owl-3 grandma h_6___n a__u+'\ growled it 0? Hon III. (24 pts) Give the organic products for the following reactions, or provide reagents and conditions to carry out the indicated transformations, as requested. Be sure to note product stereochemislry g ' and/or regiochemistIy wherever relevant. You do NOT need to balance the equation, show byproducts, or show any mechanism. 0 at“ (a) “ o 0/ ('5 CH3CHzJJ\o JLCHZCHG + /,\roc.o;2{ 00 w< a \_< U hexane -78 °C \ OC/OPh (2) H20 \Q—H ( ) CH 3 C 9 _. CH3 c g”: | AICI3 GHWQ 0410‘s + H3 - ' H2 ”C \ CH 3% A c6 ’ Chemistry 322bL Examination 2 page 5 July 16, 2007 (d) o g (1) Et20 \ E- CH 0. 3H3 + Li[A|H(OtBU)3] 48°C C: EU? a <2>H20 "* IC/ ll 0 (e) <O:© $03, H2304 O 03H /9%H 0‘ /\ /\G S (0 (I? H o C\ o 0 C" C Cl + Li Cu-(CH2CH3)2 Et20,-78 C / \/ / CH; H3 (2)H20 \/ CH3 CH3 (CE)——’ Li metal {/- ‘ liquid NH3 EtOH ‘ (h) 6 CH30 CHz—CECH CH O CH ~£~ CH DQ/ H20, st04 J : "‘ J CH30 Hgso4 CM 0 0 CH3 3 CH3 Chemistry 322bL Examination 2 page 6 July 16, 2007 IV. (20 pts) Provide a reasonable synthesis (i.e., minimum number of steps, good yields, good stereoselectivity, good regiochemistry, etc.) for the molecules 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 from each important step of your synthesis. Be sure to indicate if a step results in formation of an ortho-para isomer mixture, but assume that such mixtures are readily separated. C 0‘ H (a) CozH nib". \4 no, 0 ------- » if “36"" .wa @r OZN C0,.“ 0;“ CJ I I ’ N + Q‘NO‘Q A AICI3 01 043/0 )CHB CI CH) 9H5“ {I l is) .3.» E; a ’2‘, Falls Q 9-?“ (b) Using benzene, CH3C1 and KCN as your sole carbon sources, (Hint: PhCH2CN is an intermediate.) CH2\C/© H Q) Q I U o Chemistry 322bL Examination 2 page 7 July 16, 2007 V. (18 pts) Give brief concise, short, and succinct explanations as requested below. If we cannot read the answer it cannot be given credit. Afier 15 or 20 words, credit will monotonically diminish with b the increasing verbosity. Use structures to illustrate. WC)“, (a) Resonance theory (two or more Lewis structures related by 6-) arrows) works surprisingly well in rationalizing and predicting the reactivity of organic molecules, especially considering its simplicity. However, in one type of situation that we recently encountered, resonance theory fails completely to predict the correct reactivity. Give a specific structural example involving four or fewer carbons to illustrate this failure. Mew r A“) H 9 A A . o) ‘iVHQ 4T0. =7 WOWWHC bO‘VR Grovm‘hc -: i-I'qrolma‘i'l‘c . 1M We. >0" A?) H’We Quin “:31 HWQ MQVOYKJFC A“) 2W aramc‘i‘l'C (b) Vinyl chloride adds anhydrous HCl but it does so more slowly than ethylene. Even so, the product is 1,1-dichloroethane. Explain these effects. CH2=CH2 fl» Cl—CHz-CH3 C I— OH: CH2 slower CI—(IZH-CH3 (not CI—CHz—CHz-CI) —Cl ‘3' GD / ’Hu ___.» cut—CH3 (Jig: CH1 2 (50% JW‘OM 5‘14le {ABM “2:39 $ stable, +94“ TS: Eor Q'i’euéicho. bEmufl Q.) (9% C\ induc+fu¢ deshgilléd-i-ih‘» Ll=CH-CH3 bxfl’ \hiarmaoll'cil 1?} 'AQ were Qidret «Em A Chemistry 322bL Examination 2 page 8 July 16, 2007 (c) The 1H NMR spectrum of A is normal for an alkene, while that B is unusual. B has two resonances (4H each) with chemical shifis that are downfield from normal alkenes and one resonance (2H) above 6 0 ppm. Explain. «‘1 . (3 ”WWWJ" A §m¢ exiznsiuc. men—flanam-‘rb M ()revemf Loutinuous rI‘i’ wrath? in A, M‘- ...
View Full Document

{[ snackBarMessage ]}

What students are saying

  • Left Quote Icon

    As a current student on this bumpy collegiate pathway, I stumbled upon Course Hero, where I can find study resources for nearly all my courses, get online help from tutors 24/7, and even share my old projects, papers, and lecture notes with other students.

    Student Picture

    Kiran Temple University Fox School of Business ‘17, Course Hero Intern

  • Left Quote Icon

    I cannot even describe how much Course Hero helped me this summer. It’s truly become something I can always rely on and help me. In the end, I was not only able to survive summer classes, but I was able to thrive thanks to Course Hero.

    Student Picture

    Dana University of Pennsylvania ‘17, Course Hero Intern

  • Left Quote Icon

    The ability to access any university’s resources through Course Hero proved invaluable in my case. I was behind on Tulane coursework and actually used UCLA’s materials to help me move forward and get everything together on time.

    Student Picture

    Jill Tulane University ‘16, Course Hero Intern