Question

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The Road Map: 16. Give structures for A-F based on the information provided. [12 points] CH3CI HNO3 No Reaction AICI3 H2SO4 B (C10H12N2O3) A m/z 163 A is an aromatic compound NH2NH2 -OH H2 Pd/C Br2 hv D (C10H15N) 1H NMR on next page C (C10H1302N) E (C10H14BrN) ΚMnΟ4 F (C7HgNO4) HNMR Spectrum for Compound D 6H 2H 2H 2H 2H 1H, multiplet 0 3 2 6 5 PPM

Answer 1

ANSWER- A s aramatic compound Ths is odd < spnuctue ofA- per nitnginue it present in tis Ceppunt moleulas weight and nitro gen N- Camfimmed tht As per giren maleulay frula ofam ound whch s the prduel of A alter nitration the maleulary Famuta a ssume We amoound A- oHNO 10 H-2+ 22 Index CHDI) Hydogen Defuiciony NH2 aYMatic -TTus cambound is $pucture cmpound A CHCH3 CHa Fnedal craft Reachon Thes compaumd give Nitration fempound mde culas formula of shows the mo A gires comp ound B and cemfoound B - mmonitahm product. The possible aat o and p-basitiom accupoled which nitration So nitrahion bara bosition Psiti Anaes ocars act NH2 NO2 CH3 -structure of compoound B ZCICH Ds the wolf Kishner Reactian Product Carbonyl Compound of Campeund A, Canvert he NH2 which s spucture ompound .CH CHo CHa

given NMA Cormoound e 7 Cempound D NHo 2H veed singlat HAmae ame ptenn Tha pectra of tortr) H CH3 CH CH CHS H deublet mulealuy fermula ifere theydrgenatn Rechn t itmaans it- he wte cmaund panecu Conmpaound Thus D punecHuur NO2 in pace of NHa sbudare of cemound CHK CHS molewlrr formula cempound E CloHI4BrN mncbroninatin which fCompound D. amine cccuts at structrre ofcmound E= NHO CHa CH2 Cemla ound E mele culat fomula whch in thu oxidised pvdud cemfeound tucture of omoand E 7HSNO4 NOS the CooH

Road MaD Nihrah on) NH NH2 No FHa CHad HNO3 cHa No Reacan Alds (Frcaal CYaft o=2CH-P H sa4 A m/z-163 B CLOHPN203 As an aymtic Compound NHONHA CWol Kishnes -OH NH2 BX NH2 CH3 CHE CHCH CH PdcDCloHISN Cotychagemater) CON CHa B27 H2 EH CH-CH ECGIOHBN) CH-NMR TUsh fi cd (inaton) c CC1OHN KMnd4 Joxidation COOH FCCTHS NO4)