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ps7key - Massachusetts Institute of Technology Problem Set...

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Unformatted text preview: Massachusetts Institute of Technology Problem Set 7 Due Aim“ 9‘ q {"A' 1. Propose a synthesis. _ AW rt Vi E5115 iii?“ “fig? g/ 5‘ / . 7,, w m 5.12 Spring 2005 2. Provide the major products. >:/+ c: G ,4.» +/‘““ (CH3)3CCH2CI, AlCl3 3. Toluene is ortho, para directing while trifluoromethylbenzene is meta directing. Explain, using resonance structures in your answer. «"y /‘\A 1‘ "l ("57 \\ ‘-\ LN; ( " ) 1 Y e l I J/iwxé H )/\\: I /’//‘\Q-\‘ //\\\ Iv /§‘ \ ll,l Lima -l li\¢ \”j \/' + / M" C" V "— ‘xf ’\_ ~/ 1,? A r; can 3 ) H \J inl- ‘9 gum liq/s? “0 J)” “C 9' "A J 3 [IV ( L‘A“ v36&104.)/ _ -f’f ' “3 : HAAIA 0‘06“qu HQHLM «fill-0 t Tim. follow co Clj ‘3 Plpr‘y‘W ch" at x ( u & \r)?“¢:_g1\4...tfi.. $3) (flu/u M DA V (E; (‘1) If CF} ill) figs \I) Y ‘ 1 // />‘ |_ r/\\- 25/ //\< V‘) \ 1 y \ \\ fa ‘ ,1 ‘ J 5’? \ , \\ ~ —‘ [Lg/— \i’fl \ >—~”\ \ M\ N0 T” . grpr‘gbu no (F3 , .2. _ WM 1 m t ion /t~ \/0 ‘ 1 Mo ‘>\” 06' A ‘ C.— (\\ ‘8 W10?) * q [C(ijp M/ . .( mug“ .m ~_».-»u., AWN,» 4. List the following compounds in order of Wm acidity. (1 = most acidic) mOfiOOHOHOOH W « 9-, E 0., w i 0 80-1”?ng G l rhaiox V Q ‘ gm __ ‘/’ O r k \k , .//'M 0 /§/ “ /"~~\é .‘\\.(/ (A /b \ \\ / ,1 i/ \ f '/" J \,_./- ’- W) W0 1 ‘m/ N “(Q59 U C) [14”de Fuji. I} 41‘ @ (LO I}: P' '9 6. Propose a mechanism. 3" \\ 14V «0- (fi‘p’w \ 1| 7. Outline a multistep synthesis of 1-ethyI-4-nitrobenzene from toluene. CH3 CHQD (3—; N02 m3 ouzer pquwtgm i5 (3h. //'\ Jig...» A 012...} U \ \:\ Ti), ‘ifl < ”‘4" {'sz \// 8.a-c Which of the following compounds can likely be prepared in a pure state by electrophilic substitution on a disubstituted benzene? Outline the method in each case. a OCH3 N02 N02 b COOH No2 COOH C N02 ozN’ :i: ‘No ode. /a.. r902 93.2% \‘ A we; 0M2 )\ (5230*! \x " i ' r301 coco i /\\ “A” ‘3 h , ( rent) \1/ H g (‘ooU N02, i /\ 0A1 r {s a was» ;pv$$’LIQ 8.d-f Which of the following compounds can likely be prepared in a pure state by electrophilic substitution on a disubstituted benzene? Outline the method in each case. you NO ‘: ll» 5 d 2 /\ w _ ~ ”-2: V N02 l‘ \ “£303 mo éilw \{/ {Saw-Wit ’ firm”); ) in lo p.301 W0 QQ N02 A wishing 23 r I". o O OH \l ' e Br (\‘l Fm ‘/ s “ i \«M— 83‘; Br {3i “”2“. f No2 kl if???» t ,. “'7‘ O Liflfi‘oou 3‘1 ~ Br COOH ‘ 9. Provide a detailed stepwise mechanism for the following reaction. Cl " \ OMe ‘0 N02 N02 MeO' Cl- N02 N02 ( wf‘rwx'b - me. 0“ “/3 O ,J K may . 0~ ,u/‘CN %’ L ”x 1"l ( H q ’” 3’ \" / \f/ \/ P301 10. Propose the mechanism of the following reaction and provide the MAJOR product. C) [t d ¥ K) ’/»>’ 4/ (L11 J A P; Ulsol + HO I) ”21} t. 0“ <9 10" O 1 « /‘:~\‘ // H'”"‘--. \ /r~: two/J 6 .3 .. i \t "’9‘ \ \ I, f \ 4, -’/t L1 // -\r_ ,,> ,7 6/ \.. fl i/ \,\ ’ A) M {‘JUZ W“; U 1 1150‘, ”Mam Santa”, or all”) / «WWW 0‘) ...
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