Chem 308_Summer 2010_Quiz 4 Key

Chem 308_Summer 2010_Quiz 4 Key - NAME ' ' 3 Chem 303,...

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Unformatted text preview: NAME ' ' 3 Chem 303, Summer 2010 . Quiz 4 Section H3 ID 7 1. (2 pts.) Draw the three most important resonance structures of ethyl acetate. 0 ‘ _ CD‘S) ‘ Q )Ko/\ @ /;’\0/\ {LE—"b “ _ E) 2. (2 pts.) Give the lUPAC name of the compound-shown below. 0 /\)J\ /% N’WiQWwafiomothXQ H 3. (3 pts.) Give the reagents needed to perform the synthetic transformation below. Describe the laboratory scale method discussed in lecture (not an industrial method), and use numbering to indicate separate reactions. as usual. 0 l. v 930% ) when, A o ' V‘ OH 9?; momenxmhrté‘tyb. N/CHa (A mg H MWQVE M v . . mm'wgg ) gr tram-i7“ ) Uriqfll )Nétzg ' 4. (3 pts.) Write a detailed mechanism for the reaction below. Use curved arrows to indicate all electron movements and indicate all formal chargesyjfou must show ALL steps in detail, including proton transfers. ' (f O O V CHZC12,NEt3 O O ' /'U\ /U\ + CHSOH ————-————-———a> /u\ + A Q o t I OCH3 08 .H /Q\Qrt3 . q \/ m ‘ 9 I t i 0 :°‘:\\ e3 ’EXVG’DAK @ O\os3 NAME Chem 308, Summer 2010 Quiz-4 Section H4 \4E 7’ 1D t. (2 pts.) Draw the structure of the major organic product expected from the reaction sequence below. 0 ol»\ \\ OCH3 1. Excess CH3MgC1, THF --————-———-—~—-» 22 l 2. H20, HCl to neutralize \/\_ f 2. (2 pts.) Give the lU PAC name of the compound shOWn below. 910 int 3. (3 pts.) Give the reagents needed to perform the synthetic transformation below. Use numbering to indicate separate reactions, as usual. .. c ... O . Br \tt ) ? 2" (“07* OH (“Em whim}? gw to hm (ML‘BQe 4. (3 pts.) Write a detailed mechanism for the reaction below. Use curved arrows to indicate all electron movements and indicatejall torm_al Charges. You must show ALL steps in detail, including proton transfers. To 0 _ . NaOH, H20, A A /U\ + CHSOH . OCH3 09 ,, ak’ g g “E33- 0 4t- :tlt‘,)C\-~\a5 ...
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Chem 308_Summer 2010_Quiz 4 Key - NAME ' ' 3 Chem 303,...

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