MT1Key_Wi02 - N U, Winter 2002 2 1. (30 pts) Complete the...

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Unformatted text preview: N U, Winter 2002 2 1. (30 pts) Complete the following reactions, e careful to give all the major carbon-containing products, starting materials, or reagents. Clearly indicate the stereochemistry when relevant. If there is no reaction, say so. 1)NaNH2 2)CH3CH20Ts \ = 3) NaNH2 .___-._:_~ grim _ ” & —\—~o H— a) 5) H30+ dilute ’ 1) g1”). m j 2,) napalm»; ?) La, Cc -——* gut” ©\( . 4) “30* gird b) 575Wun€k __..0l{— Lf, 98¢. 940‘“ V.’ wum‘fi Ht MM '- [1’ (W 1) Excess 03 H U 0 ——————> wt“ 2) Excess M628 \g/ + H OH +HO)J\/ S, c) \\\ 3) Excess H20 D 5394‘? o eh )0“? 3) KOHJA o Ofl' alléo‘guA d) V\ -——-——*f 3) Agosto)” Hw 5",,(7, 2') H30 3 H10 4) Marten 4) Pcc, QPQ/ l) Mow ) M134: 1 z 2’) g I 0 Z 0 of l Br Wuw$w “3 r H ,omePCLflu— 5W6) s a) 0} H \0 some, M M: 4) MLLS NU, Winter 2002 3 2. (15 pts) Propose a curved arrow mechanism for the following mechanisms. Show all the proton transfer steps. 3) (15 pts) Propose a curved arrow mechanism for the following mechanisms. Show all the proton transfer steps. Hint: This is the second half of the permanganate oxidative cleavage of alkyne whose mechanism was assigned as homework. 09 KMnO4, KOH R . HO,Heat 0 0 HO+ O o RJ‘W__2____, A + )L' 3 /u\ + )L O R O- f-O R R OH HO R' r 0 2w 0 up 9 “‘x Ton . ° 2% ,1? m’ U M 2 ‘OH '* H’ K h .5 a 0 0 rte—[haul Z415: NU, Winter 2002 4 4. (20 pts) From methane as the only carbon-containing starting materials, propose a synthesis of the following molecule. You may also use NBS, tosyl chloride, pyridine, FCC, and any inorganic reagents. 00m 03’ km“; CZCHLi/le» MVWMM m PLC.'D§90)%~‘w—WMM MIMQ JAM w an E ‘03“ w/wv‘x“% W C:(_ M t; u.) (0» fly} Nat M Ma / rcc out 0” “L AW mam um» NU, Winter 2002 5 5. (20 pts) Suggest a sequence of reactions for the synthesis of the following molecule from propioaldehyde as the only carbon-containing starting materials. You may also use NBS, tosyl chloride, pyridine, FCC, and any inorganic reagents. ./ J/fi /‘ ’ ma Mt- ,zm m c=c wtec l 090* (“7’0" 21% WC, ,quT V/( Pa 4/ Nagy}. NU, Winter 2002 5 5. (20 pts) Suggest a sequence of reactions for the synthesis of the following molecule from propioaldehyde as the only carbon-containing starting rhaterials. You may also use NBS, tosyl chloride, pyridine, FCC, and any inorganic reagents. J O 4, $4, QLH —-——> ———> ———> u 0 O OH [H Tommi/wt m. VAWaLQLNWW)&LMM mflm’ fi/H “45% “15%) /\ + g) ‘- \/fi—(+ A wo H (no. \ 043m. r Q ~ ‘7’”; J] Wild; mimics h: M H 0“ tr cu H/i/V WY 2’) 55 OIZva/L} l9 Llfmgf M j pk 88m 9L 9 w“ 7 also“ 5”" M [to Lat/m CM M17: NU, Winter 2002 6 6. (20 pts) In contrast with Cr-based oxidation, Swern oxidation is mild and can be used to oxidized 10 and 2° alcohols to aldehydes and ketones (a little bit more difficult but doable), respectively, while leaving C=C and C5C bonds intact. Suggest a sequence of reactions involving at least one Swern oxidation for the synthesis of the following molecule from acetylene as the only carbon—containing starting materials. You may also use the Swern reagent (dimethyl sulfoxide and oxalyl chloride), NBS, tosyl chloride, pyridine, FCC, and any inorganic reagents. O O M 269 g 5 J=L9 8 (9?: w 1 Co Liter/Li %’ “LC/=0“ W 8A 31 M VJC a, I) HUM), —/ ) 9N. 21"; Q3] WWL é W 9 Wei-“(r21 : _/ ‘f‘ > pa (,2le M 24*: kwhuo‘z £5 #JL/A __ (MAM \ W‘ g“ W5 3k I “7’ 1 xi? /\ A.) Kl + l 1r“ 'r" 1W R { NU, Winter 2002 6 6. (20 pts) In contrast with Cr-based oxidation, Swem oxidation is mild and can be used to oxidized 1° and 2° alcohols to aldehydes and ketones (a little bit more difficult but doable), respectively, while leaving C=C and CEC bonds intact. Suggest a sequence of reactions involving at least one Swem oxidation for the synthesis of the following molecule from acetylene as the only carbon-containing starting materials. You may also use the Swem reagent (dimethyl sulfoxide and oxalyl chloride), NBS, tosyl chloride, pyridine, FCC, and any inorganic reagents. QJLWW Q é / 0 060 flahn’ll. a> 2\ 1> 8 L > Z)“: 9&0th 0* 04 2“? aria \LPB/LJ em» (9 (Aw/S) H’L —\ NU, Winter 2002 6 6. (20 pts) In contrast with Cr-based oxidation, Swern oxidation is mild and can be used to oxidized 1° and 2° alcohols to aldehydes and ketones (a little bit more difficult but doable), respectively, while leaving C=C and CEC bonds intact. Suggest a sequence of reactions involving at least one Swern oxidation for the synthesis of the following molecule from acetylene as the only carbon—containing starting materials. You may also use the Swern reagent (dimethyl sulfoxide and oxalyl chloride), NBS, tosyl chloride, pyridine, FCC, and any inorganic reagents. / O 060 fiahn’ll. a> 2\ 1> is L > Z)“: 3)Lgo“M 0* 04 2% 3,46 \LPB/t} emu, (9 LwLaus/S) “‘7. a ...
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This note was uploaded on 06/12/2008 for the course CHEM 210-2 taught by Professor Coddens during the Winter '08 term at Northwestern.

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MT1Key_Wi02 - N U, Winter 2002 2 1. (30 pts) Complete the...

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