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Ochem 51A Midterm1Key

Ochem 51A Midterm1Key - Page 3 1(12 points Draw two major...

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Unformatted text preview: Page 3 1. (12 points) Draw two major resonance structures for each of the following compounds, including all lone pairs, formal charges, etc. Use curved nomenclature to show how the first resonance structure can be converted to the second. Assume the atoms are arranged as drawn. H sue. CHsNoz H C N 0 L3“) H o 0 SC". (-3 \ 3cm H002 H c -o 2. (4 points) Use the symbols 6* and 6“ to indicate the polarity of the labeled bonds. - 64' 40’ 6’ ‘0"? 5 U“ L7 3 Hac—OH HO—H 0...; 9 .“ll0 l l 3. (8 points) Draw another resonance structure of the following ion, using curved arrow nomenclature to show how the first resonance structure can be converted to the second: L:l¢£. Sow-IP‘C + prmX-Acws (.9 0:63!”ng : HécfQF—QTfl-QHZ’ H3C-C=C-CH2 ll C;— Lgdlflflm) HH ’2 H p, Pr H “a i. 13 4. (8 points) For the molecule nicotine below, indicate (a) the hybridization of the atom, and (b) the number of hydrogens on that atom. a see. mp H58 6? (amok Llos II ZH\$ Page 4 5. (8 points) Circle the hydrogen atom in vitamin C (shown below) that is the most acidic, and draw two resonance structures of the conjugate base. 5 cc. 1"?“ 6. (8 points) Write a stepwise reaction sequence (curved arrows required) using proton transfer reactions to show how the following reaction occurs. You will need to think about both acid/base chemistiy and resonance structures. H 0’ H O , set /1\ + no9 *0 Jk ’ CH3 H30 CH3 6 ‘8; ‘6 . l. OIflAér\\ e)# 7(;D E9 H [/fi:\ *— C}:fl4 A 11o; 11.4311 r—a / ./U [2‘ . 7. (8 points) For each pair of compounds, indicate which 18 more acidic by circling it, . :- e sentence explain why. Use chemical drawin s to illustrate our answer. m "v?— 1 H2 Due +17 m uéDNMMLeA flm'i‘ «A a 850 H3O COH Copdwyfl'?’ bflse, 0'?— l6 (ENE) .610 Mm+ 098 .3 41411912 Maw A09 V9 ffigDe/go ___________________________________________________________________________________ DWQ, +0 «We Nemuwc. (flew “Fl/1Q m ' CINOH ‘ . 111?, 141% all D 15 Mom. 1-1%» G NLW mom) 41/1011— OSPC 6611003, 1‘. fit/WWW [é mom cLec‘tPonefiod Va (LL/V069 < FW00 8. (4 points) Circle the compound that has the higher boiling point, and, in one sentence, = . . why. \ Has—CH3 F New ngn mica/11 a 1L Stt an»: . D 1' “1.1:” E ¥DW9M9$1§0LIW9CM WNfl 3 lb 31“: (6 points) Draw Lewis structu- for fit the m of penmne (OJ-In). me. ...
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