*H-NMR Spectroscopy Worksheet Part I For each of the molecular formulas shown below calculate the index of hydrogen deficiency (IHD). In addition, suggest three possible chemical structures that are consistent with the degree of unsaturation. O. o oO 3) GHW EHD=1 ANP ALOK AY ° b) CHO LAD= O a5 ov 9 O| Co Gig CH=CH ~ CH EC~CH,O-C2CH o) GHyo INO=S {os (oN 3 2 ° ; Ps Ne NO. L_ waa, So oO Ory a cuno, THOS (OY GY OX coon, Oo Co 3 Oh 7s, RS A e) cH0, IND= 2 Ce cinch InO-2 ayPart i For each of the following chemical structures a "H-NMR spectrum is provided on the following 3 pages Match each compound with its “H-NMR spectrum. Draw the structure above the corresponding spectrum and clearly assign the chemical shifts to the appropriate protons on the molecule. om f CH, cys aw 1 ° p-ethylanisole ‘-pentene 3-methylbutanal 2 9 AK, aa AA KA & diethyl malonate butanoic acid 2-bromobutane Lo Ny o™ ae ous 4-propanol 1-bromopropane diethyl ethylmalonateCH CH, CH, OW He We Ka He a aa 2a o Woe He J J) Mae al Ch, CAL OK, Br Wa By Be _ | (ze) - Bea Ke f ian ia tw lw eo ow Ky. br Cy CH, CH CH Ma He Ha Hp |e 40 38 36 34 32 30 28 26 24 22 20 16 14 12 10 okClg ° e L 2 CH, CH-CH2~ CL aa 8 i a He Me Re hae | > h c Hee ee o Hy sam A T Te rT rare TTT TINT TTT TTT S250 48 46 44 42/40 38 36 34 32/30 28 26 24 22 20 If 16 14 12 10 08 06 Os ppm He ny Ha Me Moe iu h ow o WR OO W 3 = | Re f Jy Ba as BT an a dom e 8 Pi 4 Cn, -O-E-CH,-C “OCH CHS, a Ha He My Be Bei we ese We CH, CH, Ci, We Hp Ke ook He 2 CH CH, CH.~ “O18 Ha Me Be Ha ez ea [ he f & et @ 18 pm on ant m Ne Me “ Me He 0 HA Re Be Chg cu,-0~€ - cH-@ -O- Ch, Ch 7 a Che Me " feo hs : WaPart It ‘Shown below are the structures of two esters. They are isomers and the only difference between the ‘two compounds is the orientation around the ester functional group. We have provided the "H-NMR of each ester in the next page. 1) Match each compound with its “H-NMR. 2), Draw the structure above the spectrum and assign the protons to their appropriate chemical shits. Ae oO [ y benzyl propionate ethyl phenylacetatePart lv The "H-NMR spectra of the following pages represent mono, di and trisubstituted aromatic compounds. Also included are disubstituted compounds as ortho, meta and para. The compounds representing each spectrum are shown below. a) Match each "H-NMR spectrum to its compound. b) Draw the chemical structure above the spectrum and indicate the protons on each chemical shift. You do not have to assign each specific peak on the aromatic region. f é Ho Fon, ca ow 2chiore-Snivobercaldehyde _—tsobutlberzene on on no, 10, o-nitrophenol m-nitrophenol A on i by co-vanlin oH phenol mylene on No, p-nitrophenolOKn HA, ha fm "Tot r T Neh - Ke AON - Re MOL J - 1 wes eh kot wes 82 Spm we Che Ge Fee] BN Re - oO Ss spas dea py Ox, NM ny a o 70) ono 4 eS ' Ay Wa Offset @ 10.5 ppm singlet integration 1.0 Ne(Offset @ 11.2 ppm broad singlet Integration 1.0 ag be Wy TT Tae ep Ep Sa 5 G8 66 64 62 60 58 S654 52 $0 48 46 44 42 40 pom He ~ Oly oH 1 oye 4 we Be My Ha ‘A Ee] Gel oe 2 he NOa at 9108 etn srt hy one Ga a on = = a as : vy Me Me Fhe SSIES SESE ET EET]ct 9p ma 3 OHe i uy fd “yor aa STi, 4 4 } f ee r iin he | Ae He Offset @ 10.7 ppm broad singlet" Integration 1.0