Solutions_Manual_for_Organic_Chemistry_6th_Ed 499

Solutions_Manual_for_Organic_Chemistry_6th_Ed 499 - s±ep F...

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20-47 Products a boxed. (a) All steps are reversible in ±n ±cid-catalyzed ester hydrolysis² (±bbrevi±ting OCH 2 CH3 as OEt) Step A p r ot on oN ³resonaNce stabIlIZaTIoN´ Step B nucleophile attacks h - B is the acId catalyst :Bµ is the coNjugate base, ±lthough IN hydrolysis reactioNs, water usually removEs H+ STep C pRoton off Step 0 pRoton oN Step E
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Unformatted text preview: s±ep F pro¶oN off ! :O-h 1 .-±²³ .. :O±H 1 + v c'OEt :O-h :O²H 1 1 a³A C ´Oµt ¶h hC 0 + + :O·h h ¸ \ :O-¹ h 1 C + C ( 'OEt :OºH Ot :Oh» step B 1 + / \ .OH C¼O:½ • 2 ± • • C¾O¿ I V:REt H "± i ² S tepC V : REt A 1± A²a) S tepD ³ +kÀ :Oh c± t 1-EtOH ± same series " + \ of resonance ´µ¶ . E-±² , ( H S tep ² forms ±s above ·¸¹º " Step F Ii :O, 494...
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This note was uploaded on 02/27/2010 for the course CHEM 140 taught by Professor Wade during the Spring '10 term at Whitman.

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