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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 are boxed. (a) All steps are reversible in an acid-catalyzed ester hydrolysis. (abbreviating OCH 2 CH3 as OEt) Step A p r ot on on (resonance stabilization) Step B nucleophile attacks H - B is the acid catalyst :B- is the conjugate base, although in hydrolysis reactions, water usually removes H+ Step C proton off Step 0 proton on Step E leaving group leaves (resonance stabilization) Step F proton off !
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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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