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KEY%20to%20Project%208%20Summer%2020091

KEY%20to%20Project%208%20Summer%2020091 - CHEMISTRY 3613...

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Unformatted text preview: CHEMISTRY 3613 Project 8 Summer, 2009 NAME: [[41 Name the following: 2. Propose a synthesis plan starting with toluene that will produce the following: cfi 6 0418» - + 3 ,— O Na @ k: > l-Ms‘flm— a C03‘(&‘“:['u' l O ml/OMJJL Lam @/\(OH 3 1ng H+ 55,21'ILIII‘ILQL of, m gage 3. Cyclohexanone reacts with the series of reagents A below. Draw the final major organic product. 1) C5H5MgBr in ether, with aqueous workup 2) HZSO4(aq) and heat M I .3, 3) mCPBA J” :3: M “90.96 ‘5“ -—,u) 4) (CH3)zCuLi 6th aqueous workup 83+ > (a .49 .- 0‘3 five-fiaw—a " «w ‘s Eat/£5543“ (mg-'49 I each case give the missing reagem. c) 3-penten-2-one reacts with 0+3 mama 3*- to fqrm_4:mejt_hyl-2-hexen-4-ol. 03‘ maria/9 @MC E 15:7me 0 , CH cut; Cub d) 3-penten-2—one reacts wrth ( fight, ml. to form._4=meth¥_l:2-hexanone. ._ ”.9 ” I V—aflofl’w“ wane/C ’6 fiafiwfi. 0(J_Caavé¢9- {3— 03M” e) Ham 4;; unwise reacts with the compoun below to for/r13 4-throy:§:_m___ethylbutanal. Htx 0 HQ, wr‘l-L Exam—:4 ...
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