PS_6_KEY - Problem Set #6 --'* K211 Suggested Carey 7th...

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Unformatted text preview: Problem Set #6 --'* K211 Suggested Carey 7th Edition questions: Chapter l7: I727; I730; I735; I736; l7.43 Predict the product for the following transformations. When necessary please explicitly show the stereochemistry of the product. . l (I) HO/\/OH (cat. p—TSOH) H O PhH, fl ‘ V u re ux H (ll) NaNHg, Nl‘l3 (iii) Me ABF (iv) H303 mi (i) 0504 (cat) ' o t—BuOOH, t—BuOH O NaOH /’~ 0 -- M (n) 020 p-TsOH,PhH, reflux OM 9W 5' as: Ail/Y (i)NaCN,Eth,HgO Nam Jr N 0W H Me (ii) H30+ m M “zuMnL , K0”) Me chath , Me O M (:JVMEE Zn, HCl, heat M M ME . Mt. I"! Me p—TsOH, PhH, reflux OH Me Me U0 t-Bu (i) 0 CI $01, DMSO 0 —————> NEt3, CH2012 —78 - —15 °c (ii) HZNOMe (ii) mCPBA, CH2012 O U N H PhH, reflux ‘” {1 Me Me N Me I Me O. NaOCI, THF (”) Ph/\NH2 NaBH4, MeOH \‘z ‘ /‘::7"”’ W h 3. Provide the reagents to accomplish the following transformations. More than one step might be required for each transformation. Me Me “C8u00m MOM U4 014 if?) MiroM (mimi CHO (I/CHO ffi'm—‘meu 4 ' 4. Provide a reasonable mechanism to account for the following transformations. When necessary please explain the observed stereochemistry. O NaOH,H2O HO OH Ph/[LH F’th wacky, ()1le WM!) 5: WWI : 9“ 0—41“) Q) O H30+ HO OH Pin/“\H F’th F Math: mating emd‘ : mem%[ l?" M“ 5.9 ' " 0K : ant/17h am,” {Egg/W “:1 " 5 no an i w '4? 3w rt 6:9“; m (i) NaCN, EtZO, H20 w“! H (ii) H30+ H bask we. r . when“: El" {:70 (‘9 all (“3 a: 510 ca) /1\)th dim M mm M "an O EtO OEt EtOH, H+ Meo MeO ‘i ‘ ‘ ‘ E W- N” 322% MM M " MGM”. n3 9% W “66* 10:4 (fig/’4 p K H L“ w -> m n at? :77 w Q «—~ \ H 9"" /C»» v a w 2w" “it I‘wMWktéMx 3- ‘ 23-0 pa 3'10 @fi ‘ f: h 7 T?“ “a?” ” 5:: M0 w ‘ “Mg 7’ new M0 m m 0 d“ p—TSOH (cat) 0>< H Omsk, m0 f, PhH, reflux Gamma} :- Nu” fl .o-MH’LDTS 5%’” k3 65%0H hf nggi‘x/‘Nm . . U V I ‘1 ea (~— H —5 CKH 7 E1)” b“ Lit: of“ £5434». m “(i/V “(ma m, be. ‘PWRLM‘MDRMW on? Oh 6”} me? ml, ,, 4?” )8 a “WU” H + "10 1:3 “ ’5‘“ a3 6:9 (Q) H30”, heat W WMG M Me {kt ® Me 3 , WV m K,0Kz N OH \ ° a w a M 5335 ha) Memes; \ _. M M 2:“ \ (’7 QM ei WM. a" ‘3 M m an M M u. 2 f, w H 0 _9“ Z. Illa/Z fiéw 0h M M M NIL" H O HgN—NHPh NI’N‘Ph OJL: PhH, reflux OAH , (39" 5‘ flu “4 wag/mm fl MN'MW“ @390 ékQ-nnfw ug- ffi-wum 1'7"" H h M If 5......2 ax“ a? *‘ er? L, Wit?! ii ‘1 v H M “[90330] aatb W»? pal/week. ijbfi‘éfiafinm —;« 112;.) @ UFBU O H2N-<(2 05 )t—Bu A: Me ' fqW Me M firm (fafifgmacid Egg“; if Me a . M“ 0W4“ -Av Man/C $55241 "A" m x '4 all “U a; @W’ m 9‘7 #3} M I . > M "a, M, We: a w 6.. W1. ‘ e“ ‘3? 4?»? Mfr/w, ‘W‘ ,0, (a ‘ M‘ka “’A‘r WAV WYU‘M a M 5? “M / WV 1% ' a" ‘47 ">2 N‘N' (a; h e——-— <33§> Mfiw‘vz H 34 5 A:\ " 9n (é “ MM! OLFJ (i) BuLI DMSO H Phsg/Vph HY/K/Ph Bre 6w" (ii)PhCHO ph m ‘ ' ‘ » ' ‘f‘g’ ' an v m Eur” L“ C; "247 @»\M m@ Q "Pet ’4’ H g 4/ NM , 5 ~ a» 7 3? EDS J 144,14 ‘9 \ Rébfik Hibr h 1/ 3‘5“? g) 9 him Wig/b + k P“ Q (i) NaH, THF W PhaPACOZMe {A BrG (ii) PhCHO W9 1 H “PW/\cobm -:«-—=’s> 17113:) H “Wg‘ Rwy“: gr" M06“!wa “ u“ mm (250 r S. pd*l~ 4‘30 nu‘ak O K mCPBA b CICHQCHQCI MLKOMRM 5. Perform a retrosynthetic analysis on the following molecules (work backwards) from the given i commercially available starting materials. willlawaow O/_\O o Ph/,'\o s / H Km iii-Lela l l l‘k/‘l‘Sw‘Tl‘lP q - 5" x H a; ,K/e‘dw h/ mu , reflux H > /©:OH \' :> O2N ' H Br OH \ B" MM; / ° MW newrav bm‘fluuwl (max. [0] N Br WH :> MeO ‘ V Piliw'ékv , _/ :7 ‘“ M0 \H/on (0:31:23) WW/ Omar/Laid Lila) M50? ...
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PS_6_KEY - Problem Set #6 --'* K211 Suggested Carey 7th...

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