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Summer 2001 test 2 - Chemistry 228 Test 2 Nameik ‘ wow...

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Unformatted text preview: Chemistry 228 Test 2 Nameik ‘ wow SSII 2001, Dr. Wells. Score = scantron x 5 + essays = v0 x 5 + 50 =‘ ‘00 a Name these compounds. (5 points) 0 We“, v£ (gun‘s S ) Pm \ «r? 1 Br OCH3~ Br Br Br Br Br 0’ URN/U “NB‘Q’K ' H 7.431 91‘ 3’, Q ~ N‘LK‘OKOVWO ban bane Draw the structure of these compounds. (5 points) p-xylene WL 2,4,6—trinitrotoluene o-chloroaniline Two essays follow worth 20 points each. ESSAY 20 points. ‘Isoxazole is aromatic. Use molecular orbitals (V SEPR models, drawings, and words) to explain. Consider what is required to be aromatic. F? I VN: PGI¥6$ (W'AQ 1soxazole ESSAY 20 points. Consider the electrophilic aromatic substitution of bromobenzehe. Draw the areniurn cation intermediate and resonance structures that result from meta attack and para attack of the Cl+ electrophile that explain the experimental observation that the bromo substituent is not a meta director, but is a para director. Be sure to label your drawings and use words in your explanation. =Br: . (5;: . (gr: . (5;: O. + 92: 6/.) 99 V} (7; _—'—'—> meta attack \ M ‘\ M \C H H a C (4 l none’ 0'? ‘\"’\L rwmmm swash/5 an. Sh‘ol\‘(2d’ or Magma: .. :Br: Scrufinize 1'he reacfion sequences beiew for ques‘l‘ions 6 CH CHCICH /A1Cl CHICHuCTH-le mm /_!—;L> 1 - ,. Hm; H330; 143534 —'—'-'ru—-—h-"'_—hl- O \ CH3/u\Cl M101: ml 3 rem} —'I- Compound is most Hicer CII-L {HI-1- CII-L Cl—Al—Cl CH r—C—Cl C'H '—C‘—-F iI-{ZCHJ‘H C‘H-—C—(.‘.l I- Cumpreunri 'w? like? TH Eli TH . - I f-H<;—C—CH= CI—-A1—C1 qungfTH H2CHICP’3 CH3—c—H V /®| \ CH- ‘f—“H CH: CHEFTHECE |.. Ar—CI CH- me CH- (TH a CH Compound 3 'st like I 5.- I'll 4. Ctm‘npimnd 4 1'3 r1105; iikrfly N02 N02 NOS NOS @ \ mom l - m SO3H $303H 5 Cwmpuuml 5 is mm! likeiy C! OH H ('.'H-. I . [ I 0% /CH. I Cf—Al— C1 L'H ——C—C] CH3—C:D C ' CH3—C—OE I ‘3 a :91 6 CGmpnuml ismasiliknly H CH: ‘HI (K /CH3 1) I ' 3 H | a c —C—C1 [TIi-;—C—OH c.‘113—c=0 CHg—C—O E‘. Cl (:1 ' Cl 7 . The low yield of the ortho substituted product can be explained by ‘ Cl 5% 10% Cl 85% B. considering the “para-searching” ability of C1+ ©considering the large size of the tert-butyl group D. resonance stabilization by a lone pair E. the inductive effect of alkyl groups C A. the nonplanar benzene ring of the reactant 8 . The hydroxyl group (—OH) is an ortho/para director because A. it is an electron density withdrawing group B. it is an electron density donating group E C. of sterics / D. of induction ® of resonance 9 . Bromine is an ortho/para director because A. it is an electron density withdrawing group 6 B. it is an electron density donating group C. of sterics / D. of induction @of resonance Which compound below would exhibit the most aromatic stability ? @@ A B ® D. They all exhibit the same aromatic stability. Mob)? p \, Amp ...
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