Week 6 Worksheet Answers - Organic Chemistry [I Week 6...

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Unformatted text preview: Organic Chemistry [I Week 6 worksheet Not for credit Identity whether or not each molecule below is aromatic or not. For the aromatic molecules, identity the “n” value, describe the hybridization of the orbitals on each atom, show the lone pairs of electrons on heteroatoms and indicate what type of orbital they reside in and whether or not they are involved in the pi-system. For non-aromatic compounds, describe which requirements for aromaticity are notD met. 3??" Z a, " 1 6’- \) K a. (I 'l N N's N‘““—‘_N / z/ ) ' 4 ) 4 7. 6 ” a he; Mrs» M ’ N N ‘ I + /V + aromatic; ’ TF 3 [aroma/Wr— ‘ ' A/of‘ aromq‘h'c. flrorwa I c a e, _ 5 3mm %+2 ~e,n:( 6 V a." one 5P3 meg,“ 6 7T «1 F %+z:e «mi ’1" 0// 5,21 ¢fl+2=6 nil I as mwiomnr ‘ / 0H 5’31 draw“ on W] Iona (l/( sf 2' {I . P2 f‘ Tr /Vfinian¢,5 lane’— Pawfis ll“ $.02? lone,- par? 0 e‘ r/l 5 [no I"? :91. L - I Draw the chemical structures that correspond to the following name?‘ P“ r "‘ P N 0" b01710”; [Me +Diuenc. I Fair {A ? p—nitrotolune m-chlorobenzoic aCId 2,6—difichloro—4—fluoroanisote {aH \‘\—~(\ ‘/ HQ an as: r 0 Provide names for each of the following chemical structures: i NHZ Br 7 GI Q H ' Cl Br 0 (D - ch/csroamyr‘n a Efijkovc Ci 6C! RI F / 3’cizbromp —§:ah/aro barf—Zena / M~rk0propj be r) Eula/chi] c/a Given your understanding of acidity of nitrophenols, how Would you expect the pKa of ortho-nitrophenol to compare to those of meta—nitrophenol and para—nitrophenol? Draw the relevant resonance structures to justify your answer. . 0H OH fl) ‘ gums $\oe / . e /0 e 7 'I - $ o-nitrophenol ? ' m~nitrophenol pnmophem! N we . ‘ UC‘DNQ’ Ownitrophenoi Mflufif’fzh‘lw q p/(LL {hid/1.: [qr 2‘5 p'fl‘¥Y‘dP'4¢flO/j a nd be. mnc aa‘drc ‘rékccn mannl-rophenoi‘ because. 418 Q Can be. de/ocafr?ec{0rflco “flee. {OF/7‘0 group) Simzlr‘ajfi 63%; Parfa- L‘somem ,QEEE‘Q.C¢LMO+ ,st d°'?¢___.. 3/9. 51%? “5'61 Fiéflm OH 1) NaOH 2) (DI/Y .3644». 'OHg’mLP—S HO OH 1) NaOH 0‘! feo+ 743 710 ____.. Ca r‘ban 192754786 ’L 2).CO2 ‘ ‘ 3) H01, H20 “Wham: 3° '16 ’5 Quay/ac? _ O \ H20r04 —---—""“"' 0 0H cu CI U NBS —‘——-—." OH PhCH20| 1) Hg(OAc)2, H20 513M 2) NaBH4 __..__.———>- «~—-——-> 2of2 ...
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Week 6 Worksheet Answers - Organic Chemistry [I Week 6...

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