exam3answers - Provide short(2-3 sentences MAX answers to...

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Unformatted text preview: Provide short (2-3 sentences MAX) answers to each of the following questions (16 pts). 1a) Most ketones exist primarily in the keto form, but phenol exists exclusively in the em! form. Explain why. ”Pl/“MA 55 Mirna/{16, £1qu “H4145 é ____._ GM Mohmm 5472M lame ll“ kill” 1b) In the formation of an imine, we typically use a trace of a carboxylie acid and something called molecular sieves. M ”W A/ trace H+ 4A molecular sieves Draw the imine product that results from this reaction, then answer the following: Why does the pH of the reaction have to be carefiilly controlled, i.e., must be S 5? TE; Quail Fm‘ibkaifiim 0; like, flaunt; huh/Mix bet-euficL Meier H" mm -— MMPLL—QAL. What is the purpose of the molecular sieves? 7B film/WM W413“- ‘Qmi in W Hat/ham 50 7/754, 9/ng pasfihbh “Fix/aw Pmiudfi (lieu lamina) lc) Why does an optically active solution of (R)-a-methy1butyrophenone form a racemic mixture when aqueous base is added to the solution? 0 o NaOH,H20 _ Me 3H GMJr WW it“? migflih ital We exam "ll-tire Comm :5? - of anal Cm be. Hmi‘wal—ei a? HLPO Mg; 3"“ . _,. L7 Hail-l ail/«Jr *Facfl wf—lfi Mo WWUE mmfiwmziuafl meLSW iwo €;HRWi\W$ oi c>< Mimi “WPW 2) Predict the major organic product of each of the following reactions. Assume aqueous workup for all reactions. (20 pts). Fla—W O C) C} é 4A molecular sieves CD MCPBA [k )1», O AAPPhg, . W NEtzH, trace H’r #09 O '--.. excess NaOH [\5 C) H 3 equiv. Br2 _ M H O OJLH 4A molecular sieves 3a) Indicate the starting aldehydes and ketones that reacted to form each of the aldol products shown and propose enolate formation conditions (base, equivalents, relative tempera‘mre, relative reaction time) that you would use in each case. (16 pts) G O O OH M :> QK/ a ,JLH ketone aldehyde Enolate formation conditions: NdHWV-H 0 :95" agctfi‘w [@143 err Wreacngfi ‘f’ws Mahdi?! £4er T 3W *0 Kg) t W LDFR 9 as" game? 0 . OH 6) ,J i) % :> AK H 61:9 ketone aldehyde Enolate formation conditions: L'DA) THE' 578%: i Sim-i rear-5.4x; it“; 3b. Indicate how you would form the following molecuies using the indicated reaction by showing the necessary starting materials. You do not have to draw any mechanisms or conditions. C) it) 0 i 1 :> Jr 'EABi/SP (Robinson 4 O annulation) 0 C9 C2 Ct) Wk“ 0M3 ESPgLOM + \/\ (thig-type reaction) 4a) Provide an arrow-pushing mechanism for the formation of the product in the following transformation. Show all necessary lone pairs, formal charges, and curved arrows to receive full credit (8 pts). $9)ng HO ,H20 2” (:3 751% O a i i H 5 3- V“- L I N W A {a H—os 5 £29 0 :- OH 413) Predict the product and provide an arrow-pushing mechanism for the formation of the product in the following transformation. Show all necessary lone pairs, to charges, and curved arrows to receive full (gdit (8 pts). 2‘} f O H ”H H2NOH G d trace H+ 2 4A molecular sieves iri—LEL‘S 1 L, if ' [33 (/9 M QNHZ fiH H20 C-MNH l \lHatfii’agiwaH w; L’ “Q? $3“ “t" 5 40) Draw an arrow-pushing mechanism for the following transformation. Show all bonds, arrows, formal charges and necessary lone pairs clearly to receive full credit (8 ii H10 pm). {5i}? 0H 'OMe H30+ g; M 3;. gig—m.— )K/V _ ll, tel-l H, C 7/ We 9” ><O GEO/M M5 (9%}; a ’3 o-H fl [ as “‘3 OH" L/® )KN 5) Propose multi-step syntheses of each of the following target molecules using the starting materials shown. You may use any inorganic reagents of your choice. Don’t draw any mechanisms, just write the reagents needed for each step and the product of each step (24 pts). N, W Ax/ ’1 Rama-")2. Q\ i H36.) to? ”7% HO 2 MO‘B‘AQ Q.“ ‘Q\ fz‘ l D ’6 Vi xv 32.2.; \ s CH1“; 0 o HON / HG) L/ H0 RR 1 G {<0} \ 7: #Lljé' ate: \JLL» - 9 2!; \.0 F‘s 3: :53 "g 0 ”rd ‘1': /\ E N [m sci? 0' 69$ {u C) I. 03 \ 2 Dm5\// (.230’? ‘ Cf $3,663; 2. HOG} H20 3, a, i L” a? 5 “‘05) M) i\\ Q‘ LH A ”t 5 4. ’1' 4 6 g um O ...
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