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Practice Exam 1 Unit 1 Solutions

Practice Exam 1 Unit 1 Solutions - 1 Synthesis Show how to...

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Unformatted text preview: 1) Synthesis Show how to synthesize the product shown below from compounds 1, 2, and 3. Use each of the starting compounds only ONCE. Q) Q) .6) 0 7 CONVERT +0 Eng; o; @ AMI; _ Eh“: ”fllvlf MT. 3, :1 . m m AW 9 .M g IV “A CFKA Ki I @w ,, LA D J [email protected] T ‘ Ia, ; a? J ; _ k A 3) Synthesis Show, by reverse synthesis, how you would make Product A using a Robinson Annulation Reaction. Answers may be used more than once if necessary. Show the structures of the relevant intermediate compounds and the structures of the two starting compounds. O H3CO Answer i 1‘: "i u- - T u- “ u- 7- - i, E E- * n- -- ANAHSI} .' c1412. «,é HAWAWAAI'FJ kerb»: [35an MA TN: [208mm Awnmmou lemma» 1- Nut: «1/! (Mums ;. A” H-ou Hes-:5 m: 2331. 13m» _ on “an“! fl- canon. 3, am“ - all n AN Adam»? 4~ blfiaucntd' BETWEEN Tm: K, A mm“); 5‘- Comm 7m: flan”. Im A C’Mdonm an»! 6. A» A Manual-w n 71; y o v alsrflNNECW 9‘ ’ (0‘89” in: 4= ° U 0 My 4: Si \‘ L a) Q ”a. Ewan: Mm“ 421 Assam on ,. Nun-n: rug Am: Shaving mu m; ;‘c=a anus-N Naar To ml 'blsaumfim K.CMB-u | " Cowma- WU # C-EU I mm M Enu- 3- Conway..- uu-rp ”It ENMAI‘E Amen! 4 TD 1.;an anew #4hn‘b #! '5'- Co~un¢r® It”: I" “”6 W‘m‘flw khan! A)? A mutt!” 1-. 6) H “”351 ("A Problem Solving 1. What is the major organic product obtained from the following reaction? OCH3 Return! uwumi M 1.03/ Zn 9 2' m Man «cam-u: (a: sum") out, iiflm —_ ' "um—a—f-‘DS—fl 'W"___" " _ _ O“ h *fl In ———.——Q t __——u5 Am]. {3,1me N R? O kEDbm-E O DNTRAMI no M g ’ Dzouuv 5;? 7K ' —Gflb——-— .- o 2. What is the major organic product obtained from the following reaction? \JCLA 1' Phs ‘P+‘:CHCH2CH3 A. 4-nonene B. 4—ethyl-3-heptene C. 3-propyI-3-hexene D. 4—ethyl—4-heptene 1.32-1.94 ; cu emu. onvuuPuu'mnf antral! K “ans-a h RenakngiIE-T 4- mm. - 3 - yum: I I ! x :1 MK” 9; r515 Buttons Snflflfnfl Ii {IV-g)" nu? .. ~_.__..._._..¢ M..- __ _.,_.‘._._-.__ mmr 1w: Wand fly: away I ’- o A}: (mm-try; Mum'ut —* [was mm! 1 MkuMomu's '- ; By An S'N flame» “m on.- AM i ALKVI. Tnmnenufimspmuian 3mm It)? I :i fix: a. 5 =1 [1 .. Sn - 6 G) 1‘ (“9 \CN —6r f p/Q-flgb _) nigh-I3 Br : a"; l u6<cu ‘ .3 Ii m}: Au fu’ IA .5'41' mm“, A) : ALkvcmpHEuu Pmswhnim Blunts IM- DErna'I-Mmo 3 3? 5mm; use: 7» art- A Flinn/mien Yup ii * GD 9 ii PIC‘HSL Br p'CSHs-L :2 @C \ H 0Q"! ' \ Cs! 1/ . c J E) 3 ': ACID“. 7W PHuPHmiaH Yuu Mtr waumu‘a {a A r‘ cg, ' NunEvafi c Ahmad fl: A C’AAMML 6'10“! / . _ _ a!) In: Rum-r ; or ram Warns Rena-nu u 4:» Amy”: \ L O cl-lz / K ‘2: c7 7 \ cl!‘ ) 7 w >C ——- P IQHLLL AthuF + O=P|(6_H5[l 3. What is the major organic product obtained from the following reaction? 0 3 ‘ H2804 « L ' OH O H 04 - s '\ 15 crew. Ila-Minn“. ‘ 1 ‘ —-—_. , . kETBNE mmnuuecuum Glam] 5 ".9“ .4 “mum ken": HEMIkmL Falunrrou Indiana”. A a on 0"" Z O? flftmoplmi b C o/ ., k —- ———a z ' . K 30“ ‘6" NachoPI-ULE ”I! cvcu‘c Human; RWICH NOTE; / 1P1? Qfg’u. '. Ann-um M' OFV‘EN NUQEOPIHLES TD fll-JENVDES II‘EW .I I ' H on If OR ‘39 + Ron .__ \¢’ , _—.—. \ / HEHlkl'flN- kl"!- 4. What is the major organic product obtained from the following reaction sequence? O 1. CHaMgBr E! 0 FCC HOCH OH OH /\)kH 2. H30 ' H2504 " w" 1 («qu I Ramon Nata-p5 W 0"”an T # +| W ' if E‘IGNfl“ RFfi‘ENT ”r W 7 E3 fiv*rifi!_>— H -- O ~ e' e - Wat}; we LL, , ~" CH3 '32" , W .——h_Ak, W“ M ____. “A T ALDEHYJE ME. 13:;. ____-_,A Amer/)5 Efl‘l mun] ’ ,_‘ firfla cveu'c ICED"- w 5. What is the major organic product obtained from the following reaction sequence? o HOCH CH OH 1. M ,Et 0 PCC NH2NH2 é Ema—9 2. n-CsH7CH __’ W Br H20 1 ' l I 0 (than / O o O ‘ ) ‘L—II‘OII HIS“- M'. Am" H - - e; .. "3 Br Br 3‘ ® 3 GD “(“3 «(Lug :0 =0' (as "1‘1 cH—O‘ Mdflr i:E><j"”“ “b E: l (”3‘110!‘ cH—— on “End I' n i 1‘ g‘ .- u If Cum _ O 1 “VDMZINF *-—— 0 ("'NE M i (1:455. c=N-—NII‘ I M 4. Draw the structures of X and Y. (9 pts) 0 O - 1.0H'/HO OH/HO 2 q+ \C 4.4. ® \ 2A O 1 501072" A ConfigETE are-pm“: MEchmsM Rn. 7715 Human; TnnusFomflr-rouu O - a \ non/mo ’0 M + -———I5 9*" a 4 O O 0 . 0 o' ‘ 1 god L l A 1 C' . a \ ; A!) on air Arm-nu» In- M'DM *4 Jul-1;! rut {warn-)6 131m; mum (mung. uvctw ‘AAOOF'IL OXYGEN HO 6) Mechanism Write the product of the base-catalyzed transformation shown. Give a clear, FOUR step mechanism for the reaction. Each step must be shown accurately, with reagents included. All electron shifis must be shown according to the convention shown. 0000 1._OH mzo ——* 2. Heat H H ‘1 Y Ej‘vcu}. «,A cam-mm km: ‘ ‘ G169; I-mcuu km: ...
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