PS_9-Key - Problem Set #10 Swager 5.12 (Practice Only) 1....

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Unformatted text preview: Problem Set #10 Swager 5.12 (Practice Only) 1. Rank the order of the following alkenes in terms of their electron density (1=most electron rich, 4=most electron poor). Which one will react fastest with HBr‘? Explain your reasoning. H300 % 2 >=/ film H300 5 4 CHS‘S M I 2. Provide reagents (with mechanisms) to carry out the following reactions. W _ CH3 CH3 6 {g/ya 0 Wen/OH .\ + Enantiomer a O A Br /\ 831/ US? 6:) <01 3 H Vrén W 0/ 1 6:2 kV 4"" {Li—.9 H <_ .x/ J ,7 HaO/Hfiq. A J, L‘ 5*“ .\ on ¢ “7—”: r a / f5 ‘5 r “’47 fl1>uag+ 0/ w» : ~> V E‘ N Lao/Mg a W 5H\/E" ¥,°“o_t 3. Propose curved arrow mechanisms. ‘ G) O R H «w, H0H2C,,,& v. 1 . MCPBA 2. TSOH (cat) 4. Rank the following series of molecules reactivity for the indicated processes. Place the rank in the box given (1 =Fastest). Reaction with methylbromjde CH30Na CHfiCHEONa (CH3)3C0Na (CH3)3C0H E ( r8413 and?" renal) Reaclion with K1 in DMSO Ci 08' Q 9 *CH3 Solvolysis reaction in hot ethanol cu:a V\m {CHzN/\)\BV My Reaction rates with (CH3JJCOK in THF 5. Suggest reagents to best carry out the following transformation. Showu all intermediates. OH /. €003 +9933” 0" I. F5113 A PC)“, .1 4-66 55" 4. .. I fill 9. I063) R‘o’o" \/ cm?) a 2.: . 5 \x 3_ L." a? ‘6 6. Give the product(s) for each of the following reactions. Show stareochemistry where appropriate. OH ———1- TsOH, CH30H, A f W/fifqg 3’— 23 E- Br I ~£+ 9....‘1____:?¢*5 j. H E- f4,de (CH3)3COK,THF _ v C 13:3 Wt? '~-- / —-——’- CH3SNa, DMF Br CCl4, R-O-O-R (1%),A 7". Predict the major product of each of the following 8N2 reactions. If you do not expect a reaction to occur, then write "NR". Be sure to indicate stereochemistry. Br NaH (NaH acts as a base) NaN3 DMF 1. eq. KCN ——-—p acetone NaOMe DMF 8. More than one product is formed in each of the following substitution reactions. Provide the products and the mechanisms for their formation. H3C an r:fluo£4 at A, L ,. 9,495+ p“""”“ \‘a 6:3“ is 7 Er) $ M I Gr) , earmaa («447* H3CWCH3 MeOH, A CH3 Br? 6 \f/Y’ @K'fiL—CI-b )14- 53‘3‘44 /\ H ’5: 4/ ' / 76V “*5 2f" bé’cifi H’gCH T—F: 0 j‘ 4,: J 3 EtNHg, A 9. Provide a detailed mechanism for the following reactions. \ H2804 I W (trace water) .55 < V1A“"’O—§—o H “30* ’) 10. Give the product and all intermediates to the following reaction sequence. /\/0H 1.Na[—I,THF / O 2. V 3.H+;H20 @ 4, 4.P0Cl3+Pyridine 0 t3“ /\ W? 10 ...
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This note was uploaded on 02/14/2012 for the course CHEMISTRY 5.12 taught by Professor Saraho'connor during the Fall '09 term at MIT.

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PS_9-Key - Problem Set #10 Swager 5.12 (Practice Only) 1....

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