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- 5-52 The following syntheses have flaws in them. What is wrong with each? (a) .CH3 .CO2H 1. Cl2, FeCl3 2. KMNO4 CI (b) CІ CI. 1. (CH3)3CCI, AICI3 2. KMNO4, H2O CO2HQ3 Show that for the reaction: O2+2H2O+4e 4(ОН ), E(0;/OH-)=E0;/OH-)-0.0591log aoH-f) 5) 2. Synthesis b) c) a d) > .On CH3 CHO СН3-С=Сн .OH COM инг 1) CrO₂, H₂ sop 2) , 3) H₂, Pd-c 1) LiACH & (excers) 2) Tsll, Pyridine (209) 3) конви (чод) 7 cipt Асоон nisł CH3-CE IZ H 2 of
- 2) Write the major products A- P for each of the following reactions. (70 point) HBr CH,CH,OK* CH;CH,OH t-BuO'K a) Br t-BUOH Br,/ H20 F Br KMNO/ OH Zn 1) 0, 2) Zn/ CH;COOH b) Br NANH, CH,CH,I H. Li NH; -78°C d) A concd. H,SO, L. H,O/ H Br, CCl, excess NaNH, hear NH,3. Please give reasonable intermediates for the following addition reactions. (21 points) Br Н-Br Br (а) Н-СІ CI (b) H Br Br–Br Br (c) Br H;0* H20 (d) NaBH4 H;O* ОН (e) ОН CH3-MgBr CH3-MgBr H;O* (f) OCH310. What is the major organic product generated in the reaction below? HO HO 40||!!!!!! (A) OH ...... (B) 1) 03 2) (CH3)2S HO O (C) H НО. (D)
- A reaction sequence to accomplish the following transformation is: OH CH3 Jo OH (a) 1.KOtBu, fBuOH; 2. MCPBA; 3. H3O+ (b) 1. HBr; 2. NaOCH 3, CH3OH; 3. CH3COOOH, H3O+ (c) 1. KOtBu, tBuOH; 2. OSO4, H₂O2 (d)1. HBr; 2. KOtBu, tBuOH; 3. MCPBA; 4. H3O+The order from most reactive to least reactive with aqueous ammonia is (А) CH--o-č-CH, * CH,--oCH,CH, * CH,--a CH--č-OCH,CH, ° CH,--c³ CH---o-č-CH, > CH3-C-OCH2CH3 | CH3-C-CI | (В) %3D > CH3-C-CI CH3-C-0-C-CH3 (C) > CH3-C-CI CH3-C-OCH2CH3 CH3-C-0-C-CH3 (D) || > CH3-C-CI CH3-C-0-C-CH3 CH3-C-OCH2CH33. Draw the complete reaction mechanism in each step for the formation of compound C and D. i) ) PdCl (M CN), 1) -CH(CO,Et); Ph Ph. Ph (EtO,C)HC, N O li) co H- 60 - 95% R 97% de iv) Me,SnR co,Me ÓTMS Pd(OAc)2 CH,CN CO2Et 55%
- a) Complete the following reactions: (i) H3C-C-Ci + H2O A + B (ii) HO H;C. CH3 SOCI, с + D + so, (iii) H;O* HCN E F CH;CH, `CH;3 (iv) CH;CH,CH,CH,CH,Br + NH3 G + H excessIn each reaction box, place the best reagent and conditions from the list provided. 1) Br 2) 3) DEET (the active ingredient in over the counter insect repellant) 4) 5) Answer Bank Mg. Et,0 CH,CH,OH НСООСH, H,CO НСООН NH(CH,CH,),(2 equiv.) Br,, FeBrz CH,COOH HN(CH,CH,), (1 equiv.) NaNH, H,0+ CH,CH,NH, CO, CH,CH, Br SOC, NaCNPredict the products. Predict the products. Predict the products. OCH, осн, co, HCL AICI, / CuCI 1) H;C" CI AICH 2) H,0 OCH, Br 1) BuLi S. 2) (CH3)2CHCH2CI 3) H , H9CI2 , H2O Predict the products. 1) BuLi Hg*. H;SO, 2) C6H5CH2CI CH;CH,CH,CECCH; 3) H , HgCl2 , H2O