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995 Che m 21273-Post Lab Repa for Electrophilic Aromatic lodination of Vanill (E

ID: 636260 • Letter: 9

Question

995 Che m 21273-Post Lab Repa for Electrophilic Aromatic lodination of Vanill (Exp 3 3) A third isomer why , is also not observed. Using resonance structures, suggest a reason Spectra Analysis Attach a copy of the 'H NMR for S-lodovanillin (posted on Sakai), draw your product and assign peaks Results and Discussion section (2 pages max, typed, double spaced, 12-point font, attached to this worksheet) In your Results and discussion section, address the prompts below. (Note do not say "the answer to the quest ion is.." or something simlar, Instead, integrate your ideas and conclusions into the discussion) n the purity of your product and the efficiency of the reaction specifically referring to the . Referring back to Analysis question 3, in addition to resonance sugpest another reason why this product isn't seen. your product? How is your spectra different from the starting material? The spectrum for vanillin been posted on Sakai for comparison This experiment is another example of Green Chemistry. Choose one of the twelve principles and discuss how that applies to this experiment. The twelve principles can be found at this webste https://wwwacs.org/content,/acs/en/greenchemistry/what-is-green-chemistry/principles/12- principles-of -green-chemistry htmil ·

Explanation / Answer

in Vanillin Iodination will not occur between methoxy and aldehyde group because

reason 1:

aldehyde is deactivating the aromatic ring therefore it will direct the incoming group to the meta to aldehyde group and hydroxy group favour the incoming to ortho group, therefore Iodination more preferbly occur adjusant to hydroxy group

reason 2:

the other reason is steric hinderence, aldehyde and methoxy group is somewhat bulky and the incoming iodo group is also bulky therefore it will not prefer the position in between aldehyde and methoxy group.