CHM 2210 SPRING 2015 \ /\ \ 100 PTS EXAMI, 2/6/15 Ee NAME ee 1) Arrange the following atoms (Cl, N, C, F) from lowest to highest electronegativity. ( 4 pts) | - ra | / I | ‘ C Ni ce FY lowest (least) pO ’ highest (most) electronegativity electronegativity 2) Show the structures (line-angle, with any multiple bonding) for the following condensed formulas. (4 pts) Qhow () (CHy_CHCIOH)0(CH), an B e ee oe i Coit i) HA(BACCC(BNNH, 8) Which ofthe following is the srongest acid ? (one answer, 4 pts) aa (i) HON (i) HF work strony bub wet AS sbriry 05 UT —hremd mn notes 4) Provide the structure of a base that approximately meets the following base strengths: (6 pts) WW) HH wet Aide Examples” o . f sivong HC? ME, HBr, Mederate C92 Wear ro, ALcoll, CF,COM, ee MCN, magne ere page Hew, ‘Nz, 5) Please define a Lewis acid and Lewis base (one sentence for each). (4 pts) AL keynes, OC a)Lewis acid: A Spacies that CA, 4 y wylowisbass: A species Pht caw dauate a love Pair 6) Provide an Arhenius acid and a Bronsted base. (4 pts) Exnaples, Moo, M3, Cuj0H, Coy) Ete 11 | thing that cow he a ON desir A onaledl v di @nceoptig pid) Arrhenius acia:| Us 0& Bronsted Base au PAGE 1Sar key 7) Carbenes can be described best by what folowing features (circle all that apply). (4 pts) ‘iy trhatont sp? hybridized carbon atom 8) Predict the highest boiling alcohol from those shown below. (4 pts) /OH () HANH, =i) or Gi) HOCH,CH,OH (osdencrcHomon.on Not AB Mat OR Most Hobo alconet Oe 9) How would you distinguish Ak from aA by IR spectroscopy ? Please list the major difference in the spectra and provide frequencies. (6 pts) Iectone > A Behe curhongl stretch & Netro 2 Two cbe4r Witt N=O strethes A+ |Fo0-1h09 4 1300-1400 10) Providerell the resonance hybrids of significance for the following cationic seer below. (10 pts) SHOW! FOUR AND GIRGLE THE HYBRID WITH THE MOST STABLE CAREOCATION. H_ CHs x 2 os Best carbocation, Abo: Tush cotale arene hbS Chut 5 4 Choe? ove!) haha PAGE 211) Provide the Lewis structures for the following molecules or species. (12 pis) ad (i) PFs iy HON ‘An oxygen is the central atom oe No FC% ts OK 412) Provide FOUR (4) non-charged (no FC's anywhere) valence bond CYCLIC ALCOHOLS with the formula C,Hg0. Please put your final four structures in the boxes, you will only be graded on those. (12 pts) ou "2S H ou cr \ or Dw | a cis & Trans PAGES18) Shown is the IR spectrum for an unknown aromatic compound X with a formula of C3HgNO. Provide @ possible structure for X in the box shown below (your final structure must be shown in the box), Also assign the IR bands indicated for full credit. Provide the degreas of unsaturation in the box provided. (26 pts for total problem), Degrees of uneturaton = (4 pts) ST [HUT=WO=EaS1 TSCORE> 1 _1]800S-NO-De7a4 — [IR-NIDA-BEOSO + NUICL_HULL CoHaNO oF ms (— | / Ar I \I : Wi U Ge news] wea @) ma Beet | tana i [nis 0 | ot me | one ae ‘Bands (om) Group pote’ (opts) 3809 ne st fewiry oe new ote 2 FMM nse sip tt IX oars anazess — Aebyb C-HStr (12p%) 1672 C0 S Amide te16 pou Bow PAGE 4 Cy yp J pawe ¥es Aromatic 05 given | must Wave A bondone ring For Upt? -