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worksheet4_key - Chem 8A Lecture on Movement of...

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Unformatted text preview: Chem 8A, Lecture on Movement of electrons (Delocalized Electrons and Resonance) Acids and Bases Concepts Benzene rings Delocalized vs. localized electrons Resonance stabilization Curved arrows Conjugation UVNis spectroscopy Acids and Bases Skills: 1) recognize a benzene ring in a larger organic structure 2) be able to explain (and draw) how the shape of a benzene ring differs from a cyclohexene’ ring 3) draw a curved arrow showing electron movement 4) identify if indicated electrons are localized or delocalized 5) identify it a compound has delocalized electrons 6) be able to draw curved arrows and show a contributing resonance structure for a compound 7) compare and rank the relative stability for contributing resonance structures 8) provide an explanation for hybridization of an atom with delocalized electrons 9) recognize conjugation and how it impacts UVNis 10) Draw an acids conjugate base 11) Identify acidic hydrogens 12) Relate acidity and pKa values 13) Predict the position of equilibrium in an acid base reaction 14) Understand Lewis acids and Bases 15) Recognize nucleophiles and electrophiles Practice Problems; 1) Draw the resonance structures of the following compounds being sure to show the formal charges. Indicate which would be the most significant resonance structures. [j l )L Q U 0\ O O \— ’OH O + O' / ‘P x/ / N- C ”7 l L» mos+€i < {WK/2 “‘QCO‘H“ —___—_’~_‘_ L} O\/ 9:5 O: 4 j ‘" A» M G10: !\ / 06> ca ws are morL empm an $.6ch flow 5) Mom swam 9'64"” 2) Compare the two protons clearly shown in the following compounds. Which of these two protons is more acidic? Begin by drawing the two conjugate bases and then compare. H (-9.. H 'H we - A H x {audio 5/ H kg) H .. ' 0/ - O CMjugfllE has: i Conjugate base 2 vvlk/ W» out: H\S/\/ H c-_‘ 6.. MO: .‘c. {/9 H '_ 0\ “VS" ‘N\/[ /N 6 N ;___._____,A Y‘ Ne H/ \/ /’9\ \ H ? F F /F V F frank“? wah “/0ng "M9“? 0—H -. " 3) Predict the position of equilibrium for the following reactions. (Le. whether reactants or prod favored at equilibrium) H20 +CH30'Z.’ OH' + CH3OH j>rooluc~l$ Squared AA’QA A OH Wad” d5 Kauai/(J 4) Rank the following molecules in order of increasing Am. OM: ML ucts are 5) Write the products of the following acids and base reactions, and indicate whether reactants or products are favored at equrlrbrrum. (Use the pKa values from section 2.3) “‘5 knf ‘91: q l O .4,» :0: \/H\ + “0% 6/ \}1\.%. + ”Of OH . ' ' lower tics " e 0 /U\ + + __/\ 2:2 /U\o H t 1" 0. \/\ OH H20 ' Qauim’e’L V\Nh2 + +OH3 er” ) =7.3). The pKa values of the three groups are 6) Draw the structure of Glutamate at physiological pH (pH ave a charge)? shown. Is there a pH at which glutamate will be neutral (no group will h / K1315? COOH ‘E + l ii i ll! ~39 H3N—-C-—H .. vb: l H i“ “ K E). ['— . CH2 C‘JOOH ‘flml @153 Wm m Madurai. ’H’WYQ {9 not A (H Whey/'41 8IKMM“LC 7) From the following molecules determine which are Lewis acids and which are Lewis Bases. NH +H Qua} _ a oak Law 5 l gw’ 5 Dialok . bay W OH _ o hast OCH wi )1 v a)" I + Cl—Me . OH \ “Ms anti “Mgaoo’i (‘39de O H——-.Br H/ \ an»; Lew {S ).H . a at b ax aadl 8) From tlTemNing molecules determine which are nucleophiles and which are electrophiles. nucleofhh AlClz had ”We ’Cl ' . Q‘ZLHOQWW 3 BH3 Brnudno 9 Mi L2 elecnowln Le - MW, hm, OH W l ...
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