Exam 1 Key - NAME last first 810 CHEMISTRY 2211 EXAM 1 Be sure to read each question carefully Partial credit will be assigned where appropriate

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Unformatted text preview: NAME last, first 810# CHEMISTRY 2211 EXAM 1 February 02, 2011 Be sure to read each question carefully. Partial credit will be assigned where appropriate. SCORE 0nl answers written in the boxes or on the lines will be raded. 1. (14 points) Draw isomeric structures with molecular formula C4H6 that satisfy the 1~ following criteria. a) Three cyclic isomers that contain two Sp2 carbon atoms and two 5103 carbon atoms Ba 4+ b) Two chain isomers that contain two sp carbon atoms and two sp3 carbon atoms. Bonus c) One chain isomer containing four 3192 carbon atoms TOTAL f\% (1) One chain isomer containing two Sp2 carbon atoms, one Sp carbon atom, and one SP3 carbon atom. 2 2. (8 points — problems 2. 34 & 2.53) Draw resonance structures for the following species and assign non-zero formal charges to each atom where appropriate. This resonance form is unstable because one of the atoms has an incomplete valence. It is an important form because it illustrates the electrophilicity ofthe carbon atom. 3. (16 points) In boxes associated with the straight arrows, write the hybridization states of the indicated atoms. In boxes associated with the curved arrows, write the approximate bond angles of the indicated atom as determined by its hybridization state. (W T :1); 201 l :10” H30 I CH3 _ e _@ (Nu/CH3 \ _. 5.2 \ 4. (8 points) Consider the structures below and list the letters on the first line that correspond to the molecules (a through i) that contain polar covalent bonds. List on the second line the letters that correspond to those molecules that are polar molecules. T 1|: F\ H C:C CH OH 02020 /C"~~..H 3 F/ FF H \F H/ \OH a b c d e f Molecules containing polar c0valent bonds: CL] C} d 1 e ) "F Polar Molecules (dipole moment (u) is > 0) d g e a g NAME 3 last, first 810# S. (14 points — problem 2.48) Consider the following compounds that contain acidic hydrogens indicated in bold type. or pr or. AL... Acetone 2,4-Pentanedione Phenol Acetic acid pKa= 19.3 pKa=9 pKa=9.9 pKa=4.76 Each one of these acids was reacted with sodium bicarbonate, NaHC03, the sodium salt of the conjugate base of carbonic acid (H2CO3 pKa = 6.37). Write the acid-base reaction equation for which the reaction equilibrium will most favor the products. Write the acid-base reaction equation for which the reaction equilibrium will most favor the reactants. 6. (10 points) Tenormin (atenolol) is a fl-adrenergic blocking agent used to treat cardiac arrhythmia. Circle and name (6.. ketone, carboxylic acid, and so forth) the five functional groups found in Tenonnin. Hit/Um: 4 7. (15 points) FTIR spectra 1-5 are shown below for the following 00mpounds. Examine the spectra and identify the compounds by writing the appropriate number for the FTIR spectrum under the structure of the compound. 0 OH CH OH COOH IW TIIISIIITI'MEHLI a: :1 IIDD $000 2000 15W [000 SID lilva EN Ht (DD “no mo IDDI till] 1000 no IRVENUHI E! I -ul "00 [DD YIINMITTIOCEHLI g 3000 3000 NAME EDI! [Gal 5 last, N‘ENUHIEI‘ -ll INVENUHI I!" -I1 IHVEMEFI -II “III III] 15“ [m IMO 1W0 first 810# 6 8. (15 points) Provide an IUPAC name for each of the following compounds. 23’2J 5,5- *e-mnme‘m‘m. ,/ 3*ET‘H‘H. 4—(2-mmwmmopw.) 9’1 4-*5°1‘-UT‘“— 3 — Efi~NL — 4- [SOBUT‘IL-2,1)S,emTEWmm€THYLHEPTf-}NE ea “Zr rev-w L— 2 2, s, e — T‘s-rm mEfi—WL- 4- (vma-rnwwnom q HEPTfiNt 95 ex 4am ETWLETHYQ 4 -(1- M Em+VLEW4Yq~5—(J,1,1'TRIME77*VLPROPVQDELENE 2,2,9—TRLMETHYL 4‘E'TH‘EL \ 5‘5 tboFROPVL. em E~CNEWVL¢WNL; é "' [Sago-m 1_ am (E:— {2 mm ETHVLFRQPVQ of ~ ETHVL‘ e-tsozsu'rw: 5W ISQFRDPYL— 2,1,9 — TIaWev-MLDEQANE' 4% my;— 2 lfi—T'rtlnwen+\/L~ 5—Wamnsmvd -— b‘ (z—m mutant:qu Dam/~16 NAME 7 last, first 810# 8. (continued) 1, "5, (o *‘TKIIMEL‘T‘H‘IL. 4*PRDPYL 5%,..th BUT-1L m 5-6—- WEWVLPROP‘IL) 5-2:“.- Tlu-r-n. — 1,1,6 ~WgMETHwL- 4‘pRDPVL‘DC—I—RNE 113; 5* I‘RIMETHHL‘ 5“(l-ME71+YLPRDP‘ID - 4~PROPYLOCTF1NE '5)‘+ "DIMET‘H‘IL Sflm- EUTHL 5ft 5-«(1‘WE‘WVLFRQP‘VA 6 "' (I ll‘blME‘T‘H‘iLPRDf-WQ 6" I .1“ D\Mma\:LPRonL\-— 3 4~DHVIE7HVL— 5’— avmem‘umowc DETRN I 8 Bonus (6 points) In the box below, draw the skeletal (line) structure for the dimethylbutane isomer that does not contain quaternary carbon atoms. Consider rotation about the central bond (CZ-C3) of this molecule. Complete the Newman projection for the most and the least stable conformers. The C1-CH3 is shown in each Newman projection. 1CH3 10H3H Hjc F 3 H / H H CH3 CHj CH3 MOST STABLE LEAST STABLE ...
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This note was uploaded on 08/10/2011 for the course CHEM 2211 taught by Professor Hubbard during the Spring '07 term at University of Georgia Athens.

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Exam 1 Key - NAME last first 810 CHEMISTRY 2211 EXAM 1 Be sure to read each question carefully Partial credit will be assigned where appropriate

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