PS_8-Key - Swager 5.12(Due Thursday at 4PM K I Give the major substitution product(s of the following reactions Indicate which of the major

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Unformatted text preview: Swager 5.12 (Due Thursday , November 10, 2011 at 4PM) K;% I. Give the major substitution product(s) of the following reactions. Indicate which of the major products will be dominant. If no reaction will occur then indicate by writing NR and give a very brief explanation. Show stereochemistry when important. 9/v Problem Set #8 CH3 C:be __ Kn M be. (3115' 3 a» LG «NW— Br /‘ch/ (5 _~. ¢l NaCN /\/\m *—’* /\/\I +"/"‘C' Nal,acetone aflowSIx 'b‘sfl bani r's WWW C-Cl} m NaCl in” tome-12.8.2. . go be 1-6 Cba+eller3 Fri“ ' m Cl" a M M‘J‘L" M W W l 2. Give the major product(s) of the following reactions. If no reaction will occur then indicate by writing NR. Show stereochemistry when important. \// i A ’rx' E I 59wpr ———)-» -.. H HN(CH(CH3)2)2 90/ gym-m. Base “pfcrm “HAL S m bob“ +ke. (Cid/{DA digsn\'l' cred” _.+h. mgf; 8: “be if c" new S‘i‘ereocsn" W BIE Br (C 4r: 0.5 eq. S ' “x P M 5+Eoco Eon/Lav: *1 Br ”CH —_I-- * g 3 (CH3)3COK W59 “‘3 I Y ._";3 domrnm+ QW‘RFMI} ‘bn "-'-\-hm--'~ afi+?‘oer;‘o(¢nnr H' /—\ __)__ fir gr fi’r' ‘3‘. I Brz h 4— H 3. For the following compounds, designate whether they will react under SN] conditions (e.g., EtOH, A), 8N2 conditions (Klfacetone), both, or neither. Indicate the products and by which mechanism each product is produced. on! 5 Br 20 6‘“& Br FS—N/ ~5uifle 5.01.02 fig“; Ne :0 c+ me am; mi?" “6% 0+ 015.0- uodr “45.01 :0: 2%; \E} SNQNQ ad LC; 4" bionide -- ‘ s. 50 rag???” 5“ l fed: ‘00;- J! I “‘h 1.“: £1th 7 , Q ~— -~ 6&3 { ‘3 TS HC >03) NM AK 3 \OABY + .5 i we ~e stoma if :9 5°44. make as 34 C’s “LS”? {l- sua 0"— Y‘Jd ¢\n/c W 5"“ €301 NI 61+, 62+, “mgr W]: 5N3~ 5*“ VA: 6:03. $~3 i //\;r 4. //\=/ Suzi 4. Solvolysis of this compound (enantiomerically pure) produges 2 isomeric compounds. Identify these compounds. Bliuzllj —-—-b~ CgastgO Bu: Butyl EtOH Hsc A 3*, obi /, (MI-107393 ‘2 \L -——————b 20' '— ‘44- {tcg 6n- ;_ 540“ (33:01) —-________.—n .2- "H* 5. The following rearrangement occurs very readily in high yield with acid catalysis. Provide a mechanism and a brief explanation for this very selective process. Ho O 3H: // \\ l 1?? to“ til—30+ I H '- ,\ ____ + _____ “Wide “‘5’ >—\ G "‘“‘ b P 3° cf RQSOWCC Q‘LKWI‘L'E‘L 6+ 6. When alkyl halides are treated with aqueous silver nitrate, silver halide precipitates and an alcohol is formed. Propose a mechanism for the following reaction. #536 A; “'"‘ 1‘? fig; OH . Ag+ j/ 4 r H20 V . . 7. Suggest detailed curved arrow mechanisms for the following reaction. 8 .H3 H3 ‘ GEE CH3 H3C EtOH,A H + HI 1/ 9 l3: )5“ 1 )4} pt c ( {3C (-3 mg \fi ‘> f #5 / 6“ ME 50 Cl,- 50 +(‘E’wwct éA-ab‘A‘2ed 6% l =3 CHM-5 V Ar 1 5} 0'5 11 %Z* l :lZC’MJ {cf- mac 1"an 0F ...
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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_8-Key - Swager 5.12(Due Thursday at 4PM K I Give the major substitution product(s of the following reactions Indicate which of the major

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