IMG_NEW_0049 - anisole\Mll the main product be ortho meta...

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Spring 2007, I st Midlerm CHEM 282 Surrey PAGE 6 (5) 9. Sulfonation is a reversible EAS. As the sulfonic acid group is large, it can be used to force a sterically strained substitution pattern after which it can be removed by simply heating it in water. Suggest how to make product E from acetanilide (A): NH-''.2(,th tlt o 3 steps only 1 product NHt E NO, A ? l** *fYu"(ot Hqt"'t u -.(>cMt -+ / ,,*j't HCl, H2O heat HNO3/H2SO4 (6) 10. Please draw the Friedel-Crafts alkylation of
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Unformatted text preview: anisole. \Mll the main product be ortho, meta or parul,substituted? Explain the formation of the electrophile. Explain the mechanism and the directing abili$ of the substituent using resonance theory. (use back of the page if needed; mechanism means: draw curved arrows). H f{\t*\ qsNttuI^ D d:' I fA4^'oY [email protected]'+ |y+l*,:ku4 lvt( Sil-' c,3 w"-,ffi* P*" 0A4a fY Y\' *V*?_-g(f*" <-';Wn'4{'...
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