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  • Solutions of Himanshu Pandey Probllems in General Organic Chemistry

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    Parth Patel
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    complete solutions of problems in general organic chemistry by himanshu pandey A xerox copy of the original book which costs around 2.99 usd

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    Solutions of Himanshu Pandey Probllems In General Organic Chemistry

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    complete solutions of problems in general organic chemistry by himanshu pandey A xerox copy of the original book which costs around 2.99 usd

    Авторское право:

    © All Rights Reserved
    Скачайте в формате PDF или читайте онлайн в Scribd
    Отметить как неприемлемый контент
    146K просмотров144 страницы

    Solutions of Himanshu Pandey Probllems in General Organic Chemistry

    Загружено:

    Parth Patel
    complete solutions of problems in general organic chemistry by himanshu pandey A xerox copy of the original book which costs around 2.99 usd

    Авторское право:

    © All Rights Reserved
    Скачайте в формате PDF или читайте онлайн в Scribd
    Отметить как неприемлемый контент
    из 144
    Nate Sa CONTENTS Pages |ERAL ORGANIC CHEMISTRY 1.25 Byerise- (Level (1 and Level2()} 1 Exeese2 » a) 2 § Brerses 4 2. ISOMERISM 2ra7 § ercse! [Level 27, Level:2 0) and Level 333) ” § Beecse2 o 5 Eerie s B Freres Pe 3, HYDROCARBONS (Alkane, Alkene and Allyne) 48-62 4} Eercse-t (Levelt 48) and Level2(82)) 2 2 4 xerbe2 § Beenie} Beeries 4, HALIDES 83-108 8 Fuereue! [Leveht (83) and Level2 (86) 3 & Freie 01 °§ Exerke 108 4 Buerckes ww ‘5. ALCOHOLS AND ETHERS: {reset [Leveh (109) and Level 2 (113) § Bxercse2 8 Beerise 3 Execses| Exercises Ir iy 7, CARBOXYLIC ACIDS AND IP's DERIVATIVES 170.218 §) Bvevise| (Level (179) and Level 182) 19 4 Exerie? 20 8 eerie 209 § rere a3 8. AMINES 216294 § Precise [Level 216) and Leet 89) 216 Exercise? , 2» 5 Brewise a § Ererises 23 ‘9. AROMATIC HYDROCARBONS 235.270 P gxecie) (ett 9, neta asp md LeeiiGiay ee 4 Beecie? 260 8 teres 2s 4 Brerses 269 10. BIOMOLECULES 271276 4 Exerche:t am 5 Fxewise2 28 § Beerise3 1% ‘11, PRACTICAL ORGANIC CHEMISTRY 277-200 § Exercise 7 4 Gxerie2 m 8 Execite 280 12, NOMENCLATURE 281-289 §) Section 281 Section 23 1 General Organic Chemistry KAKAK LEVEL 1 @ —CHsekenonting group HOH = CHB HH? i Seated coment pera seid. 4 © Astentielcensiiniy ene 9 i) fn = Saas 8 6. 0) Enchatombas complete ott instrctare() Hs 7. @ MC~C8 hus9a-Handmorecleeton donating poup. HA—CoNn Guanine sigh sbi ater sesepting H®, itis mst sie ©) —Nogis-Aqous,stbisc non wile — Sct iso. Se tsabiteenin. a 4, 1, 2, a © o o o o ° ° ‘Hints &Soltions of Advanced Problems Organle Chantry Oa RS Acidity and, 31> HS RI HS 1 power of tiple bonded carbon is restr than double bonded and singlebonded carbon {As delocalsation of pe increases hasiy decreases and pK value Asmumberof « -Hincrensessabiliynereses, Oa oat Sabilcycanbedeidedby umber ofarH, cs HC —CHH + 5° (aehave as mcleopil) F s a lie Nit Hjc—C2SN—+ ,C—CR (Behave as elsropie) ‘As dlocalston of Ie increases basicity decreases ‘As resonance and hyper conjugation insresss stably increases. cry —En-c—cny, esa by General Organie Chemistry 3 26 n 28 (©) Stongerbase sre stronger nsleopie ifthe size oF donating atin Ispearly same, @ H—cH—cH= Freeraiclishight stabilise by elimination of, (©) Iaishighly base as isp «localised while in (1) and (I) pei elcalied. (@ Bath NO, groups re (4) in ature. So, hey withdraw & fom | somatcring. I. ~Tpowerof-Fismaximam in a) P P oa? Neg hn SEG, (©) +Aeroup increases basicly while-A/decreses asc 1. (@)_Composnd( i civerethylene compound, So, kishighy acti G-Q elocalised ive charge is 28 1 (@)_ Carboxylic are more acidic than phenol andalehol 0) Ine-ofN ispytoleisenity delocaisehanlpeofoxygeninfran. Cee ae a ne, 4 LEVEL- L@ 2 @ 2 @ s@ 60 2 2 Hint & Solution of Advanced Problemsn Organic Chemistry 2 « 4 I. { ra Ft MS, chi ron bi, uh Due to maximum -/ effect. APP, Nga PeandP, obit ofC- nd -3 are perpenicul. ‘Resonating stuctures donot involve change inthe position of atom, °0, J ant2=2 JX 2 Vis (1)ismost stabilise is neural) structures mre stabilise han (aU) and (IY) because of complete tet (IV) is desablise “lecronegative oxygen contain postive charge. H HN oe octet of N is complete 1. @) H General Organic Chemistry # ete Coal Si G I. (@,_Allareresoeaingstutres. (©) QaterorNeamnotaccommodate 1 (©) Moretepulsion een ©) Theyacisomes, (@)Theyaretustomeriesructres (©) Negative charge present on electronegative oxygen andetetofevery aon iscomplee @ wc—c=c > cH ‘Compeun contains 6 -H, 50 more hypeconjugaton occurs C bond lengths maximum n(n because of resonance. resonance sso oot in) FHypercnjugation scars fo (I) and (1V) ° © i H BR 4, 28, n 2, 2», © Cy © © © o @ © Hes & Solution of Advanced Problems in Organic Chemistry ‘Cy—Caeontsn more (=) bond character than C;—C. bond in (spare singl bond so bond length smaximum, ‘CN bond in (IV) pure double bond while in ease of (0) ad (1) ‘esnanesoecurso singe bond etconveredin double bon, Duet resonance single bond get converted in double bond (1) 5 most subse as its neural, (I) is more stabiie than (1) because of moreatracton between oposite charges, ‘Bond dissociation eneray canbe decided by comparing tabity of feral CoH has minimum BDE as this produces highly stabilise free rail we—e— cet cH (oy 8 8 O- mr-o ea. Bisbetterdonarthan NH, and—OCH (1) 6 most stabilise a all toms have complete octet. (IV) i highly ‘estulsoas Nis vel chargedand has incomplete os. (Uislrgestsstiscomplete single bond (V)isshortestastis complete ple bond. Bond length of Dincreasesbecauseofhypercnjugatin. Allatomshave complete ce stroctr in), ‘Noresonanc in ()- Due to resonance in into (=) bod, More resonance in (I. (—) bond get converted a @, a chy cut ci: —s Cu,—cH=C1,(poondgetconvened @ Alldouble bonds are rant eachatherno resonance in) Goneral Organi Chemistry 7 ” 38 3. 2 4s 4. 0. ees 2. » © © © © @ ® ® ® © @ © o © o ‘Maximum back bonding by N because of symmetrical overlapping ‘with andlowerelecrenegativiy Allatomsbave complete octetstructre, Allatomshave complet octet strstr _Xishihly stabilise asall doublebonds ar an. Tishighlydstabisesits aromatic innate is eas stabilise thn and as repulsion occur among electrons in ‘amultivediee. ener Mee 3° cation, () is highly destabilise as vive charge is present on inidgehead eso, Hs Ss pay aga i ane 18" pth sey nn, Hy, electronegative ones cc jsmore sabls than CF, because of bial esonnee ‘Sismostsabitie sits aromatic. Pismost stabilise ostisaromaic. Bh ss ‘Hints & Solon of Aavanced Problems in Organic Chemistry Ones Solution or(86-59) Hort fet opr at rh nd pre postion adit ineses ‘stability more than +/ group, " Mor effect opcate a ortho wn para postion and it decreases stability ofeation ore than “group, ‘and-effet operate sll positon butitis distance dependent ‘As. H decreases hyperconjugation decreases, stability decreases Solution of(61-68) +4M decresses stability of anion, 14 iereses stability oF anion at ‘orthoand parapostion ut or (eet operte stall postions Asc Hdecreases stably ofanon increases. atom cannot bepentsvlent I gem E—o1 Br Tele ein, Comte Chen . oo 0 @ c—{e00H, 20 gm j ©) Shlasbocukicnaiendlphdeolod mesa a ise 72 (©) ules mae ew ey ran aie yg ie? eanaomeadchaogen 13. (@)Panonhaenserammertesscng & \ tm Uy yt 28s ry —l Gi 14 Qhon ayers Siac tecrnpve een 78) Ramounide © © no we 1k 0) (aap hae oman Det xP ve °, way muon Ay thei ts eel Ca re So Ong Sop at ¢ ° N of 3 31 . 83 Hints & Sotation of vanced Prolons i Organic Chemis (© clsmestacaie (@ Aismostscidle oy oy ° ra are Aomatie ae CY i fl i rma ‘s fay (©) Alesha nd does ores with NAOH, hy ret wi ‘strong base. a 5 (b) Aliph amines re mor batethan somatic mines (©) CltsSHis more acide than C3H,OH as S — H bond is weaker than casts H bond is weaker th » (@) Ps more basi as its 7" amine, & is more basic than S, as sae inreses tendency todanatelpe”dereaeto woid tare repulsion, 9 © i. 6 a a (© -Mand-Tincrease aii, while + deceassaciy. ©) Sismostbasicbecase ofstearic inhibition of resonance, (© Mand -1 gros ‘Mand +1 groups wil Increase aie wh General Organde Chemis ut 100. 101 108, 108. He w. m8. 8. 10, m1 © © © sotion 49 corr ne cy sn woo wt pre eta nce agate a pon ue shane ase yb i ete ood os seep dct oma er esongcion ae esa g yb og eB ne necator iemicen sind runtringgcy nomneeywleoag o il at sann 2-10 Guivetiedense wom hn mtr cerarie. peepee es Seer se Sane Secteur, sore 0-15 perenne anncsne nontaic ban oho nbd irae rae we wa anti te, Ban ca An eos be ae Spee econtntontpe aes sy rte Sema Leaman coconut va eaten itine : 4 2 Hines & Solution of Advanced Problems in Organic Chemisiry 32. 0) Oiamonscisic ae ace nc” =, fo NOs 0, 123, (a) Rismostacdica thsi ctive methylene compound. Ak IR r = A 2) Qlomowaciie ee , Gen, 12, Siomainide 2 (© Qismosascu tissiphaeanine, Piumortsed pe of Pisdelocalise. * fs pase a. © 128. (@) Rlsmostbascasitisresonance stabilise afc accepting pe | 4 f i. ®) 130, ()Yand.xaremorebasicbecasethe hve one delocalized pes boa Gansral Organic Chemistry 131, 12, 1m. 136 135. 136, 1. ne. 139, 0, ©) Qismostacsie oe monn SG (©) Pismostacidiedecaseofortho ete (©) Rislens acidic Because thee is no -M effet of NO because of ‘erihinarnce © wb ew nfs (Resonance stabilise) 8 © © 0 Ot + I a © Om () Less clestonepativ have more tendency to donate electron, so asc nereass. Pi ile eae anteey nad oneal Mj eee 1. @ cr es CO a te2t ane 141, (@ Pismostbesias-ivechageis eased while QisIeastbasicas-ive ‘hargels delocalied 142. (@) Qismostbasic OY, Rit, 1, @ w—-C)-& a wo’ 189, © otauea ‘Bi ae ety 143)" (@. Olmos oferta Na 144, (b)Sismostbasicasipe“is localised, - ra 14S 0 Rlamonatso6-poweof —NO; bem of eon ine 146, (6) —COOH is moet ace and I power of —NOpneeaes aid of 16. &) on. ae rt 162, (a) _Asstability ftkene increase heatof hydrogenation decreases 163. (€)_ Sismoststbilc, 0 has minimum het ofeombuston. Oot 164 (©) Risleststabilise alkene so, has maximum value 165. (@)_Sismosttablses,hasminimam vl. 147, (®)_Priskessaciic soatackoccuron 148, (6) —NOzbecome outofplane. 18. @ 158, (6) —COOH ismost acti, Zs more acidic eto —Fpower of. 151.) Cismostbasic JN fi ree rs ih cae ‘Nap Hy g im @ Gp 153, (@)_Bondlengthotria maximus, asherenohyperconjugation, 166, (@) Pismostaviti. © Fismostbasic 1 © o 15. © @ 156, (6) chasspPeatbon, 170. m. m m. 174, 18 16, i, 178, 179, 180, 1 118, 1. » o o © @ » @ © » @ @ © @ © ims & Solutions of Advanced Problems in Organic Chemisty tequivesminimam energy ae Gan, requires minimum energy & Di ice Se ‘Pand Rares stbilise because ofhyperconjugation. (vein becomes antlaromsti. eI, eee omer *isleas stbise because ofantiromatc character, heave Sable Stability Woe Sa-Hinp, No-Meflect becauseoftarc hindrance, ‘Aste stabiliy frac increases bond energy decreases Nhaslow elecronegaiviy, No.ofeabon t Won NB, byte Pismost stabilise General Organic Chemisiry 185, 186, © 199. 190. is. ant2=6 Arona igh stb) (@) tbe sizeoelectron donating atom isnearty samethen, ionic (© Itformaromaticston onteacton with ENO. " ‘es & Staton of Advanced Problems n Organ Chemistry WA eprl Orgone Chemis a 12, (abd) CHsOH ismoreseidethan #0. ana ‘Aromatic 16 (abe) @isaronatic (issabilisebecauseofcompleteoctet. (©)cation smore stabilise than aromatic e HP a 1. 8) cy —eL8 om oer 32. (abd) 10F, > 100} >:CB>:C; —> Stabilly a pais TNS % nat xe CI 2 Ome eo) [ieee 7 i Ce —CO-— | a hare ae 38. (abe) cHH—C=H \ s sp = Blectronegative N GS pete dlocalse 4H 22. (45) shas 4M group, cand dhavemoreno.ofa-H Pk sis debe at bride’ postion. q Hy =e Ry pei deocaie Baga LO eS in a Sa 7 abe) Cy —OH and —Nliy ae lecton donating gm 20, they _) increase electron density at ortho and para position. S 7, @ba (609 —NOp Lp SH a serontining oon - Hints & Solutions of Advanced Problems in Organic Chemistry 5 08) bandchme eso oat tothey wees sable and igh ae of : heat of hydrogenation. 7 . 5 mvciol a hap owt as RONSN—R MS ones g 9 mote mays leo cty~0—0—cx "+ 2c44—3 1. © Reishascompletoctet. 2) HSH camo cept por 2 @ ise sccept = 4 FR dosntconain tps 5 © Maem ofa © @ “Compound contain 3a.—H. ae + ive chang is delocalized in al rngs. % @ Altwomsbaveconplte ocean. '% (©) ~ivechargepresent on electronegative 10 © Now-H ci ° 8-8 = General Organi¢ Chemistry 12, © Ketoismorestbilsethan enol Ceuta: Ce 3 @ +8, — Stas 0 Oda pew Lo GY ra | — CHy—C—CH;—CH 5 @ cheba fom > ah ot & Hs oH Oy t delocalized on electronegative Be 16. (©) CHy—C sneha i oad ‘ia D he w Be g — Single bond get converted in double bond w @ 2, 26, @ o © © 1 @) ‘Hints & Solutions of Advanced Problems in Organic Chemistry etree penn nn go -Asclecronepatvity decreases nicleopilcy increases, Assia nereasesasctyincreases, Anion of) ishighly sable because of2(- groups BL Nop isstrona (group CFs lesrong(-Pr0up. ot ‘ANSWERS OF INTEGER TYPES PROBLEMS, Lo: BAO omrion 2s b= ke b-§ xx AA, Ox fore 6 JO coments so Baaad 10-4 tebe sks a ae eae pote k e ‘0081 00H 2% @) HOON. CO, 4 2 cr, (Hote Seine Aanced Probes in rz Chit on Isomerism 2 @afo- staat AA, 1 F q 6 & a ‘CH; —CHhy—Br a 1. Dien pe 1 ct Bs A ‘otal steroisomer= 21423 Hs A acm ieee 0 Ze Sea Nt Si Et ecm 28 re 18 a5, 6, 2. Hints Soins of cance Problem in OrganleChemisiry fc @ fe snd fn, @ eee 0. » -G--O (6) AllDecarbohyaes have" R’ coniguaton so Cs wr =A (© Cells —CHy—CH,—> Achial molecule, o ee ie a ed teste (o)Q@ and (1 have S-nfigumtion while (ID) and (IV) have Reconfiguration, oily 4s © " <1 © % WOK @ i> en re (@)Theyareposton somes, Isomeriam yc 2 @O i -cH-CH—CH-=CH—CH;CH,CHh 1H “Teta tomer =25= 64 “Two dente group, So, = @ ‘80 geometrical isomerism Plane of symmetry. So, no optical isomerism, 2B. @ (Mandtlrnvesameconiguation, 20 30 “Hin & Solution of Advanced Problem in OrganieChenistry 50. (@) Allvalenciesoneqestra potion. So, highly stabilise, LEVEL-2 1 @ Isomers 2 © cHy—c—C=CIh sc, Ye ony, ce, ye een wo Neagle pe 3 Aotqueenn 22 een at Doan 4 © Gt ad cH vc. aoa ° ee ee ee ‘ee oo 9. © cay—o—c3%, wd cry—b—cy—cH, ei ea) thon on Hy 1m © ad Isomeriom 1B 15. 1" ». 2 24. n 2. © o © @ © Oo} © o o o © ‘Touano.ofisomer=2"-#=24-!=4 ‘They sy no enantiomer abot have one different grep. Noplane symmetry in(a) FA al cl a. yet oe oy Does not contin ¢—H R, a, x fOOH x G00 HBR HyCSASrOH en pow eon rina H, verfecn rein 00H ‘Coon arse ann f 3 Nopterotaymmey - No tev we er sre Snes 3 3. a. o @ © © » ® “© © © © Hints & Solutions of Advanced Problems in Organic Chemistry ia ‘Sh memberedeyciccompound anno accommodtelinearcharctet, hi eae A : esntngsace wo Yeo = of eon CHC aCe Y aa \ A N mH 1 AA Ny. on Br As uo & i meri LEVEL-3 2. 1s © ® ° o o @ ° © HW k 4 @ AN Se wy H fh Compound A has ceater of symmetry. Compound have plane of symmetry. Ra ty Hom ieH Botharemimor image ofeach other. cl a Si cae eo a omen nyc 2 Eien, Gio, tee i wine is is 16, 0. a ints & Stution of Advanced Problems in Organi Chemistry oX< coon cus Poor. taint oa erp aed 3 @ p 9 bstorer cficn—cfi=cri—crycrcns ‘ 3 Gee 2, “Total isomers My wagon HpoH 4 fils HOH compound cin @ mF i eee SSieeetpome fp on Hoke Gs Scant oe S 5 ecm, mate mee sf coor, x COOL, Wc on ee en39, onan E pe Fr a ° Ret she oe eo Rea R a, band c contain plane of symmetry. sineeoniguatos nrcppsten compounds eration ata Bats © Oh car > eoncenrtion in gv ee 1 length of tube in decimere a AB (Oh - oaxa8 ext; CR an demic soups a oposite 0 minim = 4268 ‘epulsion occu won, Hs (@)and(e)conainplane of symmetry while has center ofp ‘both and contain plane of yer. (@ and @) have ove chiral center while in (6) boi snes erpendiea. Ch ye ¥. Lge f m2 H— bond Samo) H4IKO wr Hence total % of ()=3741 +2518 cy 059% beth CH at tito each te. 36 Hints & Solutions of Advanced Problems in Organic Chemistry = i Ee va Na i is Samefunctionl roupbat diferent chainsroundfanctionl group. c) 2 @) st - @ © ® 4 4 —> Identical © oo C7 Fu 6.) $= Ment «© ® « Decree neh Stereo center=2 ea ‘Total setelsomer~2?=4 ” ‘otharsenantiomes. cr ORO +e OP Bf ot" oth-—Ol ae antoeach other Enantimere excess mes how mush one enantioner in exces of raceme mitre Amount of racemic mintre = 100-50, = 50% Exchange of both —Cl wil produce same malecule. 2540) 2580) ‘Total (#)-2-bromobutane = 50% + 25% = 75% Toa ()-2-bromebutane ~ 259% Rest compounds ere optically inatve. cate x cs 3 on. 100. © © ® © ac) © ® Cy} © o ‘ies & Solution of Advanced Problems in Organie Chemisry ‘Keto is more table than eol due to high BE of C=O bond (2) is esis, p? hybridisation bridsheadcarbonis desta, eee. Te Equatorial postin are highly stable as they ae aay fom each other, so uly groupalnays keto occupy his poston. i nae eas ae) neon oN: Pie pat wegl Ty Hye leet mi iatiinle cs HOH "Scn, at oe ° Sts -3 J eet a a a Ph eg Hy -ot ch ob ae a @ positon. hy % 2 8 AA mt we ot W/O i ae b % 0) 56 Hint & Sobions of Advanced Problems tn Orgone Chemistry Hydrocarbons (Alkane Alkene and Athyn) ane aoa Sa a no utes 1 ees eT ae pa a G1. (a) Alcohols undergo dehydration by concentrate acid in heat, rh th e. 20 Ea Ay © e ad eso wo hg Pape nos 0528-080 BES Sien pata Eases lo Se atic cement i tt haa cama L Lor Yonne che wo {yt Pay kK ~ a . oie ar oO TTS ees 1. 3, o @ © © co) © © 12 08-() tron nr tes LE cA9 | sree 2, o*, ont \ cr, Exc, Major prouct ow (orem) Alene ismore reactive towardlecophli addon resein, Rate canbe comparedby stability ofcarbocation ys doe go manne x oe Or O£L0-O-OfF09 O-0# 00200 eee eee x Noperonideeffectty HC, soreaciontakes plaeby crboction Hydrcarbont (Alkane, Alkane and Ayn) 2 . se win eaAod- e-O1, pee ge 36.) Regge el Br am yore, m—CH,0H orn UN, pyc —cH, 9 7-1 More sable Tne N— ta Hes aable 98. (3) Compound(a) willie hight stabiliseeocaton Bi—cry es ins & Stains o Advance Protons n Organi Chemisty mo C2 Che Che 101. (@) As BE 80. of cH increases stability inereases and heat of ascot me ET OE — ne 10s, (@) Aniitionreaction % i coq st bs 108, He(on = Higone + Acd aaa goad a 4, @ ch —> HOA Pay mi ps peas Sas Soe = yo oH ne ne CBr ne Hydrocarbons (Alkane, Aken and hyn) a 112, © Adon ake plce according to fone rearrangement amttmarkowni i, on mm. @ Te “one I fee as, =f Ne nan a a3 “ Sy i Th CHy ~ = b0.k8 Ge 2 ‘Hints & Solutions of Advanced Problems in Organic Chemistry ‘Hydrocarbons (Alkane, Atkene and Allkyne) a = = " vn ao ne Ae pw © ease aca \ eco Desens Men” | cog a oleracea tere Pe it aes aie ‘oe Ber 38s Ber aM, oy | ; m @ Re 137, () Cumulative dienes give CO, on edtve ozonolyi Tie ae Pi, (ese Wade Pe aes OK, - Oe moO wopeGn, og ea 4s. 10, ‘ints & Sohion of Advanced Problems in Organi Chomistry Se eames se Bie) ene @ @isnotatyicprose. (©) 12-productsmajorprodett low epee ydrocarbone (Alkane, Alkane and Alyn) 6s 10, 18. 18. 16s. 166, 16. 168 1. © © @ ancien ina plan heen emote. or ir Z wee —B +n —> Ci-slkenewillgvetre product. Rate canbe comparedby sabiliyofcartoration. cron re Biot cHy>Enecns iy ae o ra oo 6 Hint & Solutions of Advanced Problem in Organi Chemistry yirocrbons (Altane, Alken and A Hi Hs HC ‘6 est, . ye i OE 190.) AAR Ine, Ben ey to Xs Bee eee eee 182. (6) CHy—CHyssanraed. m0 A P—c=c— Ph m © sen, mw Reh Be, o Co mh —CH=CH = Ph—CH— CH 140,84 Ph—c=cH oH , PS, pC cH, — h—C—CH, 186, (8) Hydrboration inpresence of acs used for rym hydrogenation u w. © Sono Wp ignat e wwe 0 So 288 S88 \ “yO a © mo ei nee oa % @ fe i ees aaoH cH = % S © ane cy Be Or : O-cteco = oo w . () Res ve addition of HO accardi ki eer p00 bene relearn fe agente o eee tee ee ee Se eS NN Oi ence =o nL, Opp O45 | : no | 198) Rela of—NO; la tpl 5 ccy-o—cmery octet pdrocarbns (Altane, kere and Allyn) 21, OT Og Ox 2 dae at pee LL tes Ue ee dO 208. @) mt Gs Se 68d 0 a yd. wea ea ny ERR 0 20. a. 2a. a4. ns. 216. a. @ Hints Sluions of Advanced Problems in Organic Chemistry ‘Addition of H,0 is yn addition during hyeoboraton oxidation Hydrocarbons (Alkane Alkane and Alyn) n moO) Or an. 220, @) Addition acordingto Morkonikv'sule. am. © cr fy — g-8 Aco 223, (6) Addionof-D and-OHtisnynadtion, Pe a, ea 2 Hint & Solution of Advanced Problems in Organi Chemisiry ms © Yosc—ch 1, N= ANH Ph Wo LO S h 1. (bed) AsHinceasesbeiling point inreses a Sa ke [3 (abe) Zi/AandNalacetone arsed forlimination of vcinalialige, xh ee a 2 ‘Hydrocarbons (Alkane, Alhene and AUhyne) - om ats Hy My oe — ex ate Peed Be Tle 0 (08) Sowimtonsunaiton Adpet cls sincottn og Lhe ese Sects (0) Compound a, ay ay ne eae ‘willform dsereomer. 0) oe a so, its hyrogeation is ae ofa, oe] bey ie on ne a “ PG (aed) KOHand NaOH donotreact withacetytnic H. No reaction by Pale ™ Hints & Solutions of Advanced Problems in Organic Chemisry pdrocrtons (Akane Alken and Apne) * 2 i 2, (6) Cly—c=CH E> cHy— Cac = cHy—C+CHy bo ow Bi scthede +00, Auaod o D aa. 6 cH —cxzon MH, oH, —cme8+ cH fc, 29 B 17, (ab) Symmetrical atkanecanbeobsinedby Wertzreaction. 18. (a) a.canddhaveonly onetypeofeubonandhydrogen, 21. (ab) ales gveoliminaion escion wth LiAIy 2. ance) >> > Br +>< | coon Mets». cc", f = Dasa = 1 t 25. Ob) ao Ph—CH—CHy—cH,—cH (0 P—cH=CH—CH=C, % Hints & Solutions of Advanced Problems in Organic Chemistry iad es Oe o = OG ee a a Pe, < ASXA= x peti } s aa ey i oo Ee 38. (be) Bly base and quaterary ammonium st give last subtuted akeneasmar produc © (acid) Noperoxie effectby HI ‘srt lan te nto een 2 (abd) A> Ler aed Cee a wo a0 2. a oe 45. (ade) WF ™ wget wos >" et 46. (esd) > Revstion sour eyelibromonium on by Br. —Norearangementbyfeeraicl -+yelc transition state hy OS0y. PASSAGE-1 1. (@_DienelsinCisform whihcan form tanston sto OCR SCL NO: 2 © * Hina & Sluions af Advanced Problems in Orgone Cheniry PASSAGE -2 4. Traalkenegivemeso product whichis optically native, 5.) Electroptilicaition ccuron more subsiedalkene, be oH BN | See a | ene PASSAGE -3 7. (©) Compound sent canteen hil cnt 0 dastereome wi © ron 1 A 8 taendban caters nneniivatgdeny Pa Or dor ae s . ” @ | ao 4H or doting ene PASSAGE -4 10, (@)_Flecropilcaddlton on alone fase. eae 3 Jo a kee Sanaa cl Me Mk ‘Hydrocarbons (Alkane, Alene and Allyn) a PASSAGE -5 SNC! == NH + HCI on ot wtlelis o PASSAGE -6 oo Hints & Solutions of Advanced Problem in Organ Chemistry PASSAGE -7 2. ati Lody CH=CH + CHC, le th ee ce (Ahem s ena 7 Nae fs iLon, ca ome’ ao a2, cH oH Hydrocarbons (Alkane Alken and Alyn) 8 2A. (Aone emety Pe— CH ih aie. Osetia tel: a PASSAGE-10 28, (©) Additionof —OH and—Doveur 29, (©) Adéitionof —OCHyand—Hozeur witout rearrangement fi (tore 0, neon, nna art ao C3 sn, Cap Uy PASSAGE -11 3. (@ Free ralal obtained by removal of fH" at postion ‘is highly oa Oa ighy sa) ao Ot (ncaty ve) 4 His Solutions of Advanced Problems ix Organi Chemistry Chl thew Fa (©) S\2renton proceed with inversion ofconiguatin att cat uo se K fot atts Dxc—t—cH + D,C—C—0# als cH Racemi mix. am catty t-Lo)2BscH,—cHt—o— crs ieee 52, (©) S2resstonprocedinpoar aprotic salen 53, (6). S\2reaction proceed with aversion ofeonfguraton. oa) — st cll abe ss, Aare certo ce 86% Scr Halide % @ as nix + Mg St R—Mp—¥ Weaker RX bond hightendeney to frm RMX: uch Men + n—c—H 1% cHci,cH,—on Se citar Pern —er, HS cx crc OH eave wes < Ona . eee uence igime, ty aa R—c—cH, steel a6 ‘Hints & Sohuton of Advanced Problems in Organic Chemistry + @ Crs 8, CV» 4. (©) | 2rexction occur with CuBr, SFiebe HAC, fam Or aS eye mec ae s@ XS Ce creer, 5 oan, or Halder " » © by Na Na » @ Chas Oh ae tas ect on cane, - ao ‘oo is matin me ‘ou seHydeosy aid Ph ” m 1 7 “HOC aR co? y a if Hint & Stations of Advanced Problems in Organic Chemisty Holder 3 % @ © ao v © 3. © ° G Ws ert 8Sane Lous, aS 8 [ae Mints & Soltion of vanced Problems in Organte Chemistry ate = mh aha | Cee = OQ x Bie oe spa? Pa oy | —H Gaaa E. ¥ Ph ae “Ph Hon “ a ; a wing f + CHy = ee Ey fro nf 29. @ Millar city ie Beem —E— cy — e ace cure — #0. 0) ose 0 oe eS PAR wefan Koen wef cn Yen ° SOA ls Proaiet ; scx "ie a © instream ©) tunecinmsonina eat ow a6 ply fi Product No Sy2teaction at eidgehead and double bonded C: RE Hines & Solution of Advanced Problems in Organic Chemistry (©) Pwrilfor highly saiisexrbocaton. \ Rell form bighly desablise carbocation, (©) AcidbaseresctonofPhMBris faster ra Ph—o— if Pigs —+[C)] + h—o—Mgbe Solution of(57-65) Rate ofSy2reaction depends onfollowing feos: (1) Asthesizeofsubsrateinceassrate frectondereses ©) Asthe stability ofianstonstaeineenseerate oftestonineeases ©) _Rateotreaction increases with beter leaving groups 4) Electron withdrawing groups inreses rat ofreaction, Solution of 66.76) Rate of Sy reaction depends on following fectors: @)_Asthe stability ofcaon increases rate ofreacton increases ©) Ratcofrection increases with beterleving groups (©) leciron donating groups incressesrate ofreaction. 5 = _ =603€0-m (©) ReactionisSy2andCIisbeterLG (© Reaction isSy2 5y2reation at benzylic carbon faster. “one” LAD, G@) NoSy2resctions carbon, (@)Sy2 action proceedwith inversion f conigration. oes & MM Wolides 7. a3, 90, ” es Heo, Ry te ey << ost 1 ® © Nth Mote tet tlesniee (©) AeNOs+ 10 —+ AgOH OP oeyp a, wt Ia escort be ereae crete Getanetiy staartce seer yatta © i6« Basi ooh od Ge 767 eee oO eo Ch Cem -Caot-crecd (©) 1Pisweak base, soctimination eatin cannot beproceededby 1° 110. 105, 106, wm. 08. m, 12, us, © o © @ © @ ® © © His Soations ey Advanced Problems in Organic Chemistry yee Com XZ compound does not contain B hydrogen 2 in 2g rection sani liminaton rection, opens Bulky base anacks fom les hindered sde and Hofmann’s alkene i ‘the major product Aland that ratio ech oe will how elimination rection Br and Br ant wo eachother and will produce Saye H_alkeneasmajorprodut hs _Asthenumberofanti and Clineenses Erection nereases 4, bande wil produce alkene at bridgchead carbon whichis highly esate eet toy at rm sided ide Nolides 6, a. 8, us, 10. m. im. © © o © o o o 98 (Quaternary ammonium oxides gve syn elimination reaction Senses ml pre bid ene mao Oe. fer Kestresteadijae ns. © a aay and Br arent each ober i Q=aGoeegi= Es Q iy we Yon, rhe Yen, oH Len anes mm. I 4 Holder im. 13. mm ns. o » © © Reaction i Hofmann elimination ection. et Hic wera —cy, naman lc, cHcHcH cayceci, f Se ispooreaving groups etmann elimination smjor product. CConjugatdatkenesmjorprodut freacton. 7 ww. on cy eee a eigen po Hints & Solutions of Advanced Problems in Organic Chemistry © Koh hy ® 0 AY BEE AR BV °g [or—no gOS com bs © Soe keno BD ow ous | u Halies 9 (©) AgsO+H0 —> AgoH 151. © AnO Age 484, (©) Reactonissyn-imination, 155. (@) RewctionisSy! 155. © oc Rey i OS 100 ous & Solaion of Advanced Problem in Organic Chemigy @ "os Bian Pua OS on, y Hy Hy 0 es Cee = os ory A 1a. @ Hy cyt Hs cu we poe Siar oO Hye! ‘CH Hye" Hy eB ag E i = i t i ib we : eel 2 0.00)shmhinimentonnb Oberon Es : |S. (b,¢)both contain acidic hydrogens. T fers =O Boag 16. (Resin Qo ES An Shad? SDS SE Be Gore

    So, A) non : we oH 6 (©) Cuondise 1” alcohol to aldehyde while 2” alcohol get oxide to Ketone Aldehyde and stone canbe dilfrentated by Feng be i 20a nie on Giko. 9 Agy PN ntti nro ny Hine & Solution of Advanced Problems In Organ Chemistry (4.8) Adon ot HOH acordng to Markownikov Ren (@)>aleholscanbe prepared by ketone and RMX. (© _LIAIHyandNaBHcanotreduce double bonds. 7 aks © Ape ace ae HO @ oon a ary a Zot 19 Speer te re Onna sath or © Aspen tt OO. cca Alcohols and Ethers m Ee) — SEAOM, Cory +(CH—C—O}.C o ‘cis cay Me Oy 34 © Oomercrion demercron rescion poset witout any veurangerent 35.) Retctioninvolve electrophilic adlon of HBC alkene 112 eo a ”. © o ) 0 Oo} © © o is Slo of Avnet Problems Oran Chena t if svciticens —avaibi-en Cis Eee fi ite + fe AA ety A igs em ai New woe SO eae A Qo Gren - i 1 HO ‘ja extn do not proceed wit 3 fli, vinyl ale and phenyl lie ar pio. aaa cc: a Deeseu—auy fos a ci C=O— cc foun 50 ct 0=0—ch— cet cH All and Ethers 1 LeveL2 1.) ipl ee cheer lhe g g 2 dil Ba i Inport poe vent eter nisl ta 4 O-< ‘Hints & Solon of Advanced Problems in Organie Chamisry oH on eae cH—cHcH se Oty s Alcohols and Bthars ns a B © ° i 845 sens EH +11 —011+ Coy cee © OR SE Qe & «Loe ey = ae Q yee WC, ne 8 Hyc_O# ir eerotaan GN nytt NP + He Hy TN ey ™ pt [bu 16 16 1, ® Hint & Solutions of Advanced Problem in Organic Chemistry “OL 0 28 on e ee Sel he @) Aste ability of ation increases rate of dehyestion increases (6) Coripound a) and) conan active methylene H 0, they wil not sve ee ea oY tke Co =o, ‘ors iy [moore » ae 2 Se egg ta. eo hedo-ged Alcohols and Ethers 17 200O+OO® ‘era ‘aot ne FOO + Cpomar Opty orcs CH cain ‘OCHCH : z bier Ban wn oor ro aH Coon 07 cris ” 2 a aeemeneia Hint & Solutions of Advanced Problems in Organie Chemistry “A Ge: Cnr fete Cy tia i‘ (© Asthestabiliy of cation increases rae of eston incresses, (©) Aste subiliyofeaion ncrents rat of dehydration increases. © fon , fe 2) Poon *CO*OGa-O0, i Alcohols and Ethers 19, 2 0 Qponcia * )-foven Ps [s, on scncnon 1 re me tel Cp wale ees p posse, Bangor © oo tt ot P Rigne + 4 pa oan (©) MO exe only aly and benzylic aleobol. » Ee Gy ly ie, fe, © © Osean Oh : — Gteoscis) H 25, : ch = of ‘Hints & Solutions of Advanced Problems in Organic Chemistry Alcohols and Ethers S2d- C8 UB Bate Qa HS ion ‘han a ° ‘Br ‘Br «ao ( Cas, soy a sk HA, a. ve 20 Faso a Ho: OH th oa ray ota NN: ; 7 & on on 22 ‘Hints & Solutions of Advanced Problems in Organic Chemistry eee 9 AnH He WA Bits ‘PO CHACH, 0 0 "Yh cna ae aS | io ch eye Hy ; on (8 =o =O OG Aeohols and Ears wm \ a= O04 Ol 9 fomeimay fp cne t Be So eeea 1 eC % © WY ay j Lich aac TT. (@) Acid base reaction take place in (d) eo nner SY, sate SOE aN 126 Hint Solutions ef Advanced Problems bn Organic Chemistry a @) esha hes bs 18 6) Nei tntete rte et fgtemyt a0 a= a Pru BS Bi AO - Aye —st bos r 7 no C=O On On _1e 4°, Hr uP On CCl . 6) os + 3Ph—OH Ce ” m0 Ore LS fC ee ou 8 iu es Hy : a noe =0 as “nts & Slaions of Advanced Probloms in Organic Chis cusH eth ron 1400: wont Hoa Gh He Hci Ho, cme Li ty \@ wv cH WO, mH Cy ert P1022 © Hoh ~~ wee Ht 103. © if 104 © CHh—cH=cH+H® —> AL ae Ox<-O20"4 | Sa) Be Alcohol and Ethers im 1. 108, 1m, 6, m8, © @ o © © » o Highly stabilise con wil get dehydrated faster. ace ae Dinpaustin(n)-00- 25 2 Oooo me Ph—cH He0Ac ‘Hen eC ee Prodet . @) o om © 0 yy Hints & Sluis of Advanced Problems in Organic Chemisty ‘As elecon widen supa cand p-poston increases, at of hic tomate abstain recon eenes "ec Be sae Sanne bo he &, Mh ecto eisinintonration, concn Ore 4 Reimer Tiemann reaction, Alcohols and Ethers oy abe hss —s _ : 7 130 Hints Stains of Advanced Problems in Organi Chemistry o 5 (qe) Aleools having CHs—CH— groups give halofom reaction H (Clis—CHH, Cy CHP, . 6 (a) Hydipssofaandb will produce destabilise carbocation 1) No 5 @: Non Noy tint oS $88 @: A oy Mei 9 | | we 4. G9 moa —O) RE Pr-O + Ph—cHs—z 12. (ae) POH > Pao crea —+ Ph—o—CHcHy sen each YR — torn Mesc—oH| > meseeR cisciycr > MescO—cHCH,cH Hs 1. 69 HONE iL cyt—0-cat My, SS so +2. — ce O—ca 2A 16 (ab) Cone HyS04andKHSO,bot ae dehydrating agent Meohole and Ethers a 6 Aon B+ on 8 ew BN ay Ps cy 1G Asi ving tit pop wine B+ KOH eo OL OL cohols end Ethers ins & Sluion of Advanced Protons in Organic Chenisry eT ee an oie. NG she a “Koon” i 4 5 at Ras nucle 2 Oe = Cr aera ~ nee DL 2 a8 oe ORO 2czec coat i =: Qiggette Oo wh Patt Quah OR Bice chs x oo Nod aot ie Hints & Solutions of Advanced Problems in Organic Chemistry Alcohols and Ethers 3s Se We sccamess 1 Lp RF Ska ees 7 it Te oy AO he 2 EO oad ou Pe oa % bea D-fowen 2. 5 4 Hn H 4H H | ° fis, ti : KK moka O< + [mo 4 [on a obo (Coon Se CC a “Obs “ aE or eakicthan wan yf ox - CLS re eRe A y 4 Oy at Sioa 45. (96) Coie aid oF eto shoul be bay for animleular on race 46, (064) Reston) Claes rearangement aye ay s Bo, Reaction (c)involvestearrangement of arboation, te 8 TH i Resco) bPresreaangement 47. (abe) Alehols tat can frm sain cabot give poskve. Tet iso. wl Locaregee 48. (aba) Acidity of e-trophenl is minimum due to intramolecular Wetonding. pe 136m San Abend Pot Oram Chom Linked Comprehension Type | rasanees | fh ‘eee : ve, fon 10 Oe re OF Hs "OCoHs xe cn 2 AER ce bot aN of ’ cy wT 6o Mac: oH state formation cant be ecu, both OF are ant so tans PASSAGES “1. (©) LAI strong reducing agent Hero ee ss SNe PASSAGE-4 oH ove Kom o o 138 His de Soltions of Advanced Problems in Organic Chemistry PASSAGES Ron te ee wy o orb nm asm ouonem Lae 0 PASSAGE-6 canon cena @ Oe Lo.) —-on sie88, @ (forse. from sim, Or) dw Che Alcokols and Ethers ANSWERS OF INTEGER TYPES PROBLEMS. o ABE 2 0) RGF ° © ° o © cho, HoH HOH go, 210. ayicHo + HCOOH + co; iy—0n HO, ZnCl Poy, Py, SOC, a he Ce 10 Hint & Solution of Advanced Problems in Organic Chemisty 2 @ CDEP 9 @) boeb ee LEVEL Carbonyl Compounds Cac (© Mao iseustiverengent rb olinof ayesha @ on 2) mech —cii- Sear — cry SO htc ‘ivetes with ive tet with 2SDNP. Tolle’ reagent 4. Aromaticketoes donotreaet with NallSOs, 5 (Carbonyl wihouta-H doesnotgive Aldl condensation. 2 Be ss, a vw ee 10, a n re 16, 1% His & Soluions of Advanced Problems n Orgone Cheney (@) AcidicAldoleondensation ection (©) InamolecularCanizzao reaction, 9 ° © AA Ge, Kat + aa, (ialtorm Reaction) H © Cotes, cH co Am, or Lest mer on Akt conden PP aT g xsi ae (©) ResctioninvolvesdtonofD;0. Preosepp Da oopton (©) 3*Aleoholscantbeoxidzedby KjC140>- 2 @) a © ©) » @ % © ae a ie Beckmann srearangement ‘Aldehyde ndetone canbe diferetatedby Schifregent. emincsaisobiainby reaction between aldehyde andalecho. Leas reagenare use fer identiicationofalechols. sete 7 Na emo «namo ae on CCartonyl compound with show Aldo condensin in ofaiuebase| at ‘Mins & Solio of Advanced Problem Orgone Cheniry one 7 Gg eee em 2 apdleeleg lanier ce bag 2 0A ‘Compound is aomti in one for. Pita Pee Hemicetalsre obtained reaction eamecn dehy and oO is its & Soltion of Advanced Problems In Organ Chom» “Cartons Compounds 8 @ een OP. OT ae ome tee. ao ( )-o-ayen, eae wv ue a mae ee oe 5 Cy o Carbon Compounds cl 2H OR Foo Ko] ag a, at | cr (@). 2—Hctisalsoued fr tie reducton of —NO;t0—Niy wae po AK me, TO " 84 ¢ a NO by gouge S ws as a Ss Hes, 41, (© Aldotcondensation Ofip sop 166 a Sata Aen Protons Cram hey Pena 9 O= O20 aa 33. (2) WolfKishnerreaction 150 Hints & Solutions of Advanced Problems in Organic Chemistry (@) Aldo condensation. 6 or $ membered ring are obtained by ita molecule reston, ° A Bas. 2 e 4 on eer t y : cE oa 9 Pr Ph ° 9 © mpd ce m—otmp—f " cH cH, bla es ; yey Be es oO. OH OH ‘i "Oe GD a ‘ : Carborl Compounds at Arte jpee Lede eos 51. 0) Coniamornctin A @ ° Be Ds oe a” ‘OH g ie 4 ™ SS ‘ ai ot on ° 0 ron so(j* eee "Ay SEP OAR © SH. (©) Oxiiseandreduce roduets ofboth reactants i 55. (Retief —Phandoniéontt A Hukeple Clix se 12 ”. o. o © © © © Hints & Solution of Advanced Problems in Orgone Chemistry 2A ro C +e l ct ane, [Fm O=c—cu cH Carbon Compounds 3 ©. 0) Ciesnietnetin ov sige dn ig eee Lprbon i poe Le ey, ete se feos La) @ in aE oo Ade condoseon 14 Hirs & Solutions of Advanced Problems in Organic Chemistry "i ae ae, H i t 3 1 # f 2 5 9 " H rr 8 hes ° #. oo OK Aye © ° aT Carbonyl Compounds Iss, 73. (@ Benzin condensation oping — ou oN ; bul ° ° 14) recr—on MO mtn ee nore on (Berz0in condensation) 975. (@)_ Reaction with 24-DNP indicate presence of ebony! group and ive ‘tlm nde ° 4 Mis: O) ale tenon, ll Bt ca, om, 7 7 ‘i 1+ 64g + IBc—H > H—cmC—H + 6Ael a f 156 Hints & Solution of Advanced Problems In OrganleChomistry 5 OY & OG - «ioe a Me q i I Cx mo mtn MEO cas tov Carbon Compounds 17 OF © © © Baeyervilige oxidation reaction Insertion ofoxygen occur towardmere electron donating. © me © Ise Carbo! Compounds 102, (6) Chisencondensaton rection. ° i (AEH 8 pa Esters without cH, react with earbonyl compound is base ‘medium, knowns claisen condensation Nucleopilc aromatic subtution reaction will also tke pace, a5 Mp’? 267 BS CUR eee trad s nie @ [0 + non Hes Dew" aa webets pee 12. ‘His & Solution of Advanced Problems in Orgone Chemistry 134 (©) Aldolcondensaton 125. (b)_ Reaction isbenilic-acidtyperearangemest, 126, (@)_ Shasmaximum polar character because of aromatic charter, Den Os 1. © m—cH=cH CH or Non BE, , = H i ° ta ie roe 1 mL nat m0 yom Xe Ke te lew a aa Rae | pg = ph & a em a ie igre eens alee aes i a 142, (a) NaBH isslsivereducing agent or cartony compounds. - com EN foe A ne! Poveda ie M4 @ yp 4 Hy ISI. ©, Ces —C—H IE Cae y By k Se he 145. (©) RaneyNiapowertleeducing agent ‘ of cg — 9 3 OO : a 146, (©) Akolcondensation ection, 158. (@)_Resetonis intramolecular aol endenstion reason : c=N on, + HCH apa ie hse, cue pee a Va Okt oeib ae ddvact coare is Che eS deo, a “CHC &, db, tend, ~~ CHO, Hints & Solutions of Advanced Problems in Organic Chemistry we daacdnand oy=cp ae Qu. Sa 4 om ” Carboy! Compounds ba RO ait, Inposo—8 ie beter uclopil (4) Aromuticaldehyde and ketones donot react wth Febtingslton. 5 aft ogee) smarts Roop pect «ao rnin eee Ne ST ele Cts Meat ed ce neces i? ae eel Tai oy ° , an Gp Base ESS ol +8 a m0, 2 B 1s nis & sovations of Advanced Protiems in Organic Chemistry (0.8) Cdoesnotreactbecause of tearichindance hy man oe) Crests ind ele alae oe es oe 2 cy =a (4) Michaetadition ollowedby aldol condensation reaction, peeling lacie cara Carbonyl Compounds as Spa pos ‘ Bie “yf te le 17. ed) Ciizzro reaction, Tscenko reaton and Oppenaver reaction nvlvehyrideshit. te ae 210, 0 f OH OH x aw OC = CL 4 impact 170 Hints & Solutions of Advanced Problems in Organic Chemistry. Re ESS ee x aro tim By Bl & h i & Pe Oe tng 2. 09) os de cnc TO) —+ aac) ° le Pfs H-E-on —+ mrctie-on + -e-8 a a. (40.0) (@)eanotgivealdlcondensatin ats o—C doesnot contain, 2. ed) RCN ET phot 8, a 9 Meee, mhnensct a Lhe rex 38 bo) cre MS se im Hints & Solutions of Advanced Problems in Organic Chemistry m arbor Compounds 2 Oe PASSAGE-1 de he tbee Cr a ete eel So een 2 @ Conaina—H er i PHOS 080 Doe SO athe XD Pre SBS Do smo aot ae @ C0, HO, “Io 4. (be) ae 010, 48. (bd) Alishydesgivepostivetes wih Tolen's reagent. ° 269 an, tee ‘nese a Hints & Solution of Advanced Probl in Orgone Chemistry cere come Se, Mon cn, + oo8 me, iat iL = ee a, : i Setar 8 0) Ondnort Ledeen e o ® Passace-s P q? no nttea vai Gomes « o 3 on Lat te 74 | |. & ig FS nea tel Di. De PASSAGE. 43 2855 suntcmdereice t PASSAGE-7 1. ® meted lon | og » @ pote 7 rc ¥ tel a < Sic hnte “Sho -swbeadan et 0 = hw Oo 2 ©) Famaiosten RDS. 2. @) aire >t Bo, — sabiy PASSAGE-8 os or PASSAGES pee ere 16 ints & Soins of Advanced Problems i Orgale Chem PASSAGE-9 OO Oe | 7 Bop ae Oy PASSAGE-10 2 ® 9) w @ nccooe, 8 PL C7 “ecuGooen, ~ CH(CdoPD: | ; choad bie a nies (Ovemer acide) ao peg aoe P + =e eect? Carbon Compounds im PASSAGE-11 ot 1B ole ty Ob-© on ofl. oO ; ANSWERS OF INTEGER TYPES PROBLEMS moh drhgt AL Jade el at wi © © “ ) “ a ry) Hint Sluions of Advanced Problems in Orgonic Chemisiry Je hs J Lent Carboxylic Acids and Its Derivatives Roce j cry Lon neon S . Lm cn, —on Estat oi eo eres ae, ® —_ 1B n 1, an o @ @ © o © © @ © vba Acid and ts Derivatives 1 ° endian vo gamete nel —— Cyl ee Licu—ci, 22, no—¢—cH,—c C—O — Ec N (o) aaa ee ac mae ak gal a ae —cthy—cr,—on Es cit, —city—Br SM 9 (ey oe Jot cic: © Ronen Phe =ct4-— crews cr —c—co0H Lo @ ; A ae aL R—c=N EEE, g—cooH Sy RCO CH, » L vi et ocr, 8s exer ont + er,0H1 caison + cx —t—c1 2 cr toc « Myst 2h ee gt Coch 10011 [COOH + a bes = (©) ExterwithoutacH danotgive laser condensation fn Mints & Solon of Advanced Problems tn Organic Chemistry 2 @ © eo is hiepe BO yes uy © © Oo Oo} o lr bonli Aeld and Its Derivatives 183 [abl doesnotreduc esters. IAI strong reducing agent bag Dbwep-aeo ta som (DL +Dtg x0, Fon te wll, 22 wv Wega = 1p SOU, phat, nn I rons ntico, —+ rh-t-En8 140 + cost Ph—CHy + NaHCO; —+ @ a Pronn—o—cn, A, aio? PS 1 Hints & Soluions of Advanced Problems in Orgone Chemisry 11) oe a ee DAA oa 8 é ° —Giazen HC J 1% () Ami Eserthomologationesction. » (b) Curtusreaction 20. (2) Electron donating group increases rate of Hofnan’s bromamide reaction, 28. (Naat ec oly ebony compound and cron! clr 0 Hy Hh aa anPear, Ei uo 4 ey as cee coed ; oP are Peers on i ae 133. 0) Int method Is sep is Sy2 reaction and 3 halide cant give Sy2 resction .cooH 6. @. ek, 187 136 Hints & Solution of Advanced Problems in Organic Chemistry Carboxylic Acid and ls Derivatives ° I Alc & sonverulcepes wee OR sec > wef sco (sii) ° “6 BEES wm © 9 @ ° Ho on 5 paso cc bu, «0 2 en a b se! a co rn °. ac gel «© m4 iz, | prtnstonexcton 1 0) Chia ae of ay [8 sition fhe bons re Cheney Corba eid and Its Derivatives 1 wi dn se Aah A ao DAD ae, HLL cages GP Adam t Is St (2) Aeyeoincondensation 2Na aN 26 a= ba — o lee 3 es i a 8 “en = 56, ‘its & Solon of Adbanced Problems in Organic Chemistry 8 ice NOs oo” a No; on. Nor = Highly stabilise caranion @ we (9 Wate ins Be Hae Sw voy © Recess aii kal me ae A a a Deol SED Lise 8 ai uy group Product i arbote Acid and Its Dervatves 191 ° cae 4 Hon cH oe ost a oH 0,” 0: oH cf fae ae —s oH sit, on oo op hale ee Cf ae te oo = wae, Po he, f “coo Hints & Sotaions of Advanced Problems in Organic Chemisty Ro ee os © (@) BaCOy+H480, —rH,c0,—+ 110+c0, a © een: 19 1am T ae aa =". oan en aH h M1 Pf FN eo et ‘ a ei seria] ri me aa an is ~ ee 1 ® on 00, ae bu 8 OG rt Ge 1 SSH oad gay | oy 20 no >No | i Me ae fis ° nw fio, = Ws so? cH-on gr-ow “ Hon ye cron Hy-o1 G4-on Nee? HNoe? 78. (a) + " Ho i, cne-on Sree ieee ea mT et” eh Mints & Sotuion of Advanced Probl in Organic Chem 9 4 NG eae ot a” Tis 80.) P,0, ects dehydrating agent 196 hole Acid and ft Derivatives ‘on, q Bo pte tn ° . lee Prone Mints & Solon of Advanced Problems In Organic Chemistry b on Sey, 0. aa ei Ec, 8 cnc, 28 H—Gon Non (au I neko ae 97. (2) Misanacidbase reaction. CAL + cryo—p# —> cry + cH ch cit, oO * Ol "NO NOs OG" ots obto— oth & 198 Hints & Sotuions of Advanced Problems in Organie Chemisry 190 6) Bayeritigoxonraton Diace TD t # Me a © owner J “OT OY Say ae BNE a - Dor a Fee dy -O —dro Ph reve ro? PAT OH 200 ‘unt & Sohtion of Advanced Probl tn Organic Che me OOF — ou Corbooic Ace and te Derivatives 201 Ey? Majer cH ‘ m _— nie @ mexton #24 La sat : wo ded Om we ‘gH 4 ° I Bie “So Aes aT i it 113, (©) Ph—C—oH Shy pC} HaPABHBOL, py Cy 1a @ age Leal cone ee ao bee see sce La Soca) as ‘e- ao Hy—Ph 202 His Solution of Advanced Problems in Organte Chemistry rhoxlie Acid ond Its Deriatves ap coy E (abe) Atte aro aol wad aces af exrieion sm irene of 1 9 He—emen MS oe MA 105 B41 As the pov charge on —C— increases rte of melopil a0, I _xkitonentonneeases, REO cHycH,—C—on Hyo=c, bain ee hea 10. sa) Oh oo — Se Ro tcc —coont io eee eee ett on ees se cetyl commode tyedatioe atthe i 3% (Bo) As the subiliy of carbaion increase ratg of decarboxylation Ol > 4 (bd) Forcross Caisen condensation, on should not have a-H. Product of ° reaction fet eter 6 (60) Reaction sHel Voir Ztinski onli eid and Its Derivatives 204, ee wad “oD oS a oars a a0 = = 20. (abd) 206 Hints & Solutions of Advanced Problems in Organic Chemistry ° IC Bis (Some a. 0 (> i ( 2 Cw nto eae conan i eee el one ole am ° rect of men 8 en fd ee 9 ° I a ia oe eae BH o> crto-L cn, t g oO). @ rte GO —mtotn Er = ‘coon *° urbe Acid and ls Dervatves 207 26. (ave) Hunseckeresction 27, (abe) CH;CHy—Br + aqkoft 54 cH,cH,OH 9 on AA site, A er) ba cacti > @ 28, (bed) Beckmann’ reurangement on x Ce aa Ye a. = ° cen amie Em, 2 q ve : Zi ina e Ae wha 0” - ie = OVS an sae Co ite 9) eee Ho: 0. eo 6 Hints & Soliton of Advanced Problems in Organle Chemistry be) “ph (1° Amine), ot \ on no Lio enZstt0, thon + 10-1 Non cH, o a [Be fate eat en ; ; a oe jnoard spam f i fa, ot yah ee, be Sree ane Toy (be) Priesrearangement ° To mcon ll iat G9 Pepe BO Com Hy p—ctty-on « @ + POH © (ood) minx dase, seth es a i t mI A ton ; mA evel, boxe eid andl Dervaives 200 47. (abe) eKetoncid gem-tieid undergo decarboxylation on esting. | and 5-diacdon eating get dehydrated OO" OD yp Oo PASSAGE-1 0h, Oct 0 Kos R800 NO © © i =c=0 Hy C—O iN NO, NOs mS o © 210 Hines & Souions af Advanced Problems in Organic Chm PASSAGES ® yay ae at on g 8 o ° © ° Jeo, oe, adn. ° ° ‘Question number is aol condensation, PASSAGE-4 10 Allractin ilgvesametypeofetton. no ° Fe t cis pbolic Acid and ts Derivatives m3 22 Hints & Solution of Advanced Problems in Organte Chemistry PASSAGE7 inte hams, a os ca oy (lc ie BSAGE-9 nt rs ie Oy A A ay =r Hs Cte = Ee ph) «MOL Set Coon on Br © 6 @ é ool, ag “hs ‘ao _ I ae = ee = rar int bie earnest 5 ou Ws preset eee nay se 8 ee ot 8 gue eno 16 AK CK mY ae ethos bla ' ° » I no oy ty on, foanar ch, a ‘coon £ o : 4 ‘Hints & Solution of Advanced Problems in Organic Chemry lie Acid ante Derivatives ° eT Dove -E— 06a Crhcie—E—g—E cay cs : ord pb eo Lc, 4 nae » asl a eae hy Hs ae e N® Alls do nota with NaOH Nit, Oy cry a (Hofman bromamide i ati ar Tas cH cr 888s crc C+ (CH) —ciy— Nt Hales which can give Sy2rectio te wen Gori phhal al a ce ore +8e yoy, Sa Ph—CHy—NH, +H aqueous medium order of basic Poeor Guanine ismostbsicamine PhCH — Ni ag Nt + broek Amines 27 2. 36 (@) 3*aminehaslestnoof H-bond, (© Ine in(eia case Sis montbasi, ® 6 mon EH (© Pamin ive seohols with NaNO} HICIor HNO, ie \n SE = cl—CHy— CH, ey ci—ci,—cH~ Non, ects ny ct nC Me (Me ‘tad © foal Te) ah Maag, Ge Me, oi Me te 2c mes eb ce a L o Pm 2, Ded 10 CS HS Oe Nc soi [ae cats Cn 218 Hint & Solutions of Advanced Problems in Organic Chemistry On Oe O-O Lo teal Sense 1 (CHy—C#y—NH—C—NH— CH, 4. © CHC: LEVEL2 1. © Pamine 2 (@) Nochinleenterincompound 2 2. 1B ° 0) Ph—CH=CH = Ph— CH; 4 4 emi on— cum np © meson, son (Ph—cH=CH—NH—CH+*-Ph—Clp—CH—NH— CH Hay ph—cHy—CHy—NH—CH Once OrrOaed cits Sal oO bd ‘Hints & Solwions of Advanced Problems in Organte Chemistry HON ay ‘ aN su ous og! Gig Wana Ae Pe no ct, 8 Xo ow’ ey ne g gq » © Qed and Oyo 2 © Oyen 8 | 0 Conary hy, m0 ai Pa a ma eer aaah yer A cH — Ph aa yi s mm Be o. @ © C} © © @ & “Hints & Solution of Advanced Problems in Organic Chamisry OCD ="060 5 Seeanswer of question Na25, Reaction isintramoleclsretenton of configuration occur 1,00, OG gR-ot miner ms «= Csechn get ea 226 Has & Solutions of Advanced Problems n Organic Chemis no Om 730 © Lees + "pd © grace A AA se . aaaRCrS 2 at oe i" Donen, # O- [ i 2 i 7 a r é i a 8 ‘Hines & Solution of Advanced Problems in Organic Chemisry hs by yo «oO oO he 94, is a) ra NaNO, Het 7 wer i ro 517. (©) Hotmannseliminston ection, Nit Mite, No, (621) D—No2 ml /Ayoy wile Vicor Mayer raion eo) sar nan HS th Us —bi on 8 mba (ersten & m—cn=cn— ln Bes Cae © moe! I H—N—C—0cH, CN, Ms Ph—cHy— C= ieee us mL osm — Neos cH, 20 His & Sluions of Advanced Problems in Organic Chem Amines 21 18. (4) 2 anne ely sv nmsnanie, Prod nee ; Soeh er 2. (ad) Curtius renction —> R—C—¢ fi ® eet | Ah 1 exe me eo 2. ape) ‘H pe os clctied 2. 49 Ox ome Noy NO 8 2A. (ado) Only 1° amine wl give reaction. va an ~ my 20000, S60) og — a fro > onan ae ea eer oe Ce ele = sae cree, el ee 17, (6,4) Carbylamine reaction give isocyanide as major product. 9 Prd HC. CHy—+ Non planar, ae ON. NOp mwssage-4 NO; 1 @ 2, @) Reactintsinramolecul 3, (@)- Seequestion No-25 fexercise-1 2 His Solutions of Advanced Problems tn Organi Chomistry PASSAGE-3 7. (©) Reaction involve Sy 2rection, i hald is used then major prodet ofrectionisatkene 8 (@)_—NO;make ortho and para poston e- deficient, so hydrolysis ake place preferentially in that postions, % (b)_Sy2reacton involve competeinvesion of configuration PASSAGE-4 Go "8%, estbl compound C340) exiano teenth Nico! opal ive A Noman wr coon ppm Nountaraion tes Junie ——(©cty0s SAE 9AO coteos 80. Y Est (ow (et smeling) 11D neste then Chas —OH and—COOH group whichis confirmed ‘byBalso,Thswecanaay had has CX group, 2 ® CE ee. os Amines 7 \SSAGE-5 13.) Eleton withdrawing group inereases resctiviy of dazoium sl sy @ boon ANSWERS OF INTEGER TYPES PROBLEMS, 1 een wy iD 20 Aim. pas HN Ny yc th ‘Nh Octls 26 “Hives & Solution of vanced Problems in Organic Chemisty 3.) Only amines givecaryl amine rection, x fe t 4 © (@boem 5 )_ Only amine give Hoffinan’s mustard oeaction a aa ao ; Oren LEVEL NH, CH 1 1 Sia OO Aromatic Hydrocarbons te ‘NO, ‘NO es le O#0 . ae ae O20 ies a No, i ae ng Sores 4. (0) Temoresablebecue of svong-! power 9. (0) Cone. HNO,isseongonidingagen. 1.) 0st se oe slfonton of somatic rng. © CF meradiccting ©) Drs nad piecing, bat it give pas jr 236 1 M 15, 18, 1, 2 2s, © o co} oy © © © “Hints & Solution of Advanced Problems in Organic Chemistry Aromatic Hydrocarbons 237 NC is more setvating than —CH- », F FF pion gion gia om “a O=0 Peco teeter a “cite see, on on Oo ste ae « tao 2,4,6-Tniuophenoshiahly aie soitreact with NaliCOs, Astivatearomatic compound readily ent with azoviam st o @ @ o Sack = =6= uO Activating goupsincreaseateof EAS ection a tt oe “Or Sostt ou BL C : 5 eee iL op OS 4 S Py Hint & Solion of Advanced Problem in Organic Chemistry © © Iisfeeradical addon reaction. sand arenonromatibecnaseofronplamastuctrueien “frelon . ae sae nae » 4 or © © “OO fnvans cies ® * nN ol © 4 © @ f 2 @ > Le roa oe 1. ‘ tf “G Rt ATA paieamae F275 ane) suttiy-saonnza OM mari Hydrocarbons 29 9% (@) Compound (i) and (IV) follow (4nje & rile, s0 they are anti roma, Hs Aste aromatic compound a Activated by esnane és os 1 abba te | Goer ~ © ‘Altre ena AN pein Hy Nitin wiles according more setvtinggroup—Ollstorho andparapositon ‘Compounds having activating groups do not undergo Fide Crats ‘Aromatic compounds give elecophiic substitution reat 0 fee ‘ada substitution least ely His & Sais of Atanced Problems in Organ an oF Send oa a @ db aa or 34 (©) NO; isdeactvating group. 36. (Cone. HINOs soxidsingagent 23. (Q)_Resctionvilake place atalalyic hydrogen x4 tal Sheri Ie Reaction willtake place accordingtomare activating group. ae 0 AA My Ag, on San Ce 0 or etatin .yamay La, 2,2, Ph—CHy—Ph 2 © a a PO ao AAAS or er Pen nfo nn te oa al 2 = s Gof oye ns herepeguiooeee eee 2a Hits & Solutions of Advanced Problems in Organle Chemistry 45. © —ciisisacivaing group, 0 RE w 0 to vmo 2 yf 2 @ ‘ectldectta dhe TA Feey— & + Bei, P \romaticaminegivesuch buervaion $0. (b)__Nitration will take place according to more activating group —CH. POs LEVELS 1. @ 3B +2Fe —> arate 2s BP ono no Ame ae A U jRiey—o a 13. (@ NaNO; +HCI—+F N=O cn. ‘ % eh Hg Ay HN x0 7 ce 14. Co, Biel citing rnp. 11 etcetera a 4 ©) —Nosisdeactvating rou, soitcanot give Fredel-Crfs reaction, S © Seomplec obtained by ide ringismore sails w ‘Mints & Solutions of Advanced Problems in Organic Cmdr 2 es a ea wha, n@ a a ©) Nitin witecersednto—Cily (8) N05 = No +s ae noon = fo, + cn308 oe NO} 18 (0) OCH, creme electron dest str, sore featon become 26 Hint & Soutons of Advanced Problems in Orgone Che % © pve samerypeof carbocation, 33.) —Cliso-andp-irecting but deactivating group, 4 j Grs0, 6 © Cyan €Y spate yound coral 2NO3 pup Soringncomecleton iit oO ac waen acres i 5 remedied aan peat Oe ayer Bi t “emeto,, S)_HH9O., H—C—H 8. ©) Ss a" ‘shih acted rng, depen of 3-H © 3 “ _nBiBre 2 @ ee a fe & a NO} a ae on: mo, ae ne «0 a — Noy Nor Scr, as a Hints & Slaton of evanced Protiens in Organ cS clase ae o s. 5s. 2 © ohn Es oct oe “Orin sofa OF] Lo. ba, is a @) ace Te oo ob eif & a. 6. 65, 20 # QoL Bg me @ —CcIy—NOand—Srtsaredesctivatingand vesting, + Big= SEES ha we ©, © Fan, “eh O©+ (© Aswitawing group atari and para with eepec a leving soup incremex mot acon acess (© Formation ofieradialishighly subse atalyiccarbon. Wor esi o aaa N+ 80. (@) CH; iedonating sroupand ativan group, 481,82 -> Fallow passage-7(Exercise-3) 8 @ ni G Phy os nB=on “a © 86, (2) Desctivating groups do nat give Friedel-Crafts reasion =i aso get deactivated onreaton wih lewis acd W Ray be ole © ss ate 5S a eee " 2 Hin & Sluions of Advanced Problems in Organi Chemistry san NP 88. (6) Noaedichydrogen.So,norenctin, 4 93. (6) Reaction willoceuraccordingto activating group, mo Deep 9.6 cm O) isa ma, 5 i Om Ohs Ren? br | sees OO ROL Oa Oy. ae e Om 0 COC me im. @ chrakh—od “ me ® reo a 2O le ©~ 2. 2 tm Sano Acero Ogo Chomliny en ae 4 CE @e Oo Non planar, OTe $F = ns " b bata POX, -of Soytt aH 11, (@)__Salphonation will occur according to deactivating group —C— fh Rageenpertnprenemaectiny, us, 6, a, ma © aSem dena moro mo "= or BCH, pete pee PhO Gin wo LED Giles dl 190. (a) Desstivatedring donot give tresrearangement, ast -™ HIS iis Adreeed Prete Cre Chm MO A ai mB Na] A FOP a Jolene BOs 16 AA, on J] > ba fo nh Ho & Sates tact Poems Chmity poe De 1 08 Se, fee epee 9 wena, Rae noe a An CS ae Tg 0 e-0-O)-crman neo Ooh os [ene Ole Onn °F Worcenion cus | s11-10-O)-be 1 -(O)=on F pO x 60 (J, ao : (Om iy snd — BR eating 22 Wi Hydrocarbons 1 (abe) Reaction (a, (Pad) proce by same ype of carbocation, cr,—cu-Lery 4 So AA, DQ Eka A >a Se (4) They ollow anyxene Gposets lie] ite) + Ed me ute a Ly alt 21. (85) Compounds (e)and() ar sromaticinioni orm. b6-}:.09-85 His ee Sea ch 6s o==62O% ia ~~ O64 —o wh) ee 3h abo, ees te Aromatic Hydrocarbons 7+ ay 5a PO, 34 (abs) (Ohasnoacidichydrogen Hs and {CH areighlyaeth 3s. oo K PASSAGE-1 lee 2 © CA ; “g = 2.) pe isnot deocatied, apa PASSAGE -2 ‘5. (©) —CFsistrong withdrawing group, destabilise sigmacomplex. 266 Hints & Solutions of Advanced Problems in Organic Chemist au Cap hom Atk of £9 wil occur on meta position. . No; 8 15. @) —Nosisstparapostionwitrespectto—Ciso—Clisleavinggroup. 16. (©) Hleewon withdrawing group oro and parapositon with respect io leaving group increases rate of nuclephiie somatic subsiaien 7 () —N=0 conain pe and sabilze c-complex at ertho and para poston, PASSAGE -3 SAGE -6 1m © SS ries PASSAGE -4 © 12, (€) Deactivate aromatic compounddo native riede-Crasreaton. Od Gad 268 ‘Hints & Solon of Advanced Problems in Organ Chemistry peas 2. 2Na—2NPH2e Te ane cRamieeice paste ANSWERS OF INTEGER TYPES PROBLEMS nn 4.) @ben 8 0) @bdeenn Hint Solana of Advanced Prose in Organe Chemisry © sane ec et ah Fred Ctacylanrecon. glcrnebs . ny OCH, ote ° Biomolecules CrGcd (Only one correct © so 2 © Ea bee : it HOH o E tn, 22 ei ae scroH : : ton WA SEE at ow) eg, on ‘on lege oe ols Ccylic compound which dir in coniguraton vers tat erbon, ‘where they contain functional group. cron CHO Ho ex unborn u—fox supmie— eek) 16 @ TR" yo tw no non Hoa Hon Hf-on OH CHO am | a 2 3 Hints & Solutions of Advanced Problems in Organi Chemistry (© Ho: © (pre (Glucose decolourie Br water while fitosedoes ot decalourt, Ho Ht » » Cy} © Blomoleeles cs) uo xO » @ 0 20 2 © 4 ‘Amino acd conisin —C—OH and-—NHproupson-crbon, Peso a tsk » “Ewiir ier earl ES 5 yee FS On? wae Yon a t ji Y BNO ds boon Loon emt ence parece erage earls Iisaeeipeteig ong i Gn = ° q C—O ismore acidic than Rit, Hint & Soins of Advanced Problems in Organic Chemisry 00" 00H PhCH, CHS, = PhCH, A Biomolecules as (abo CHO HOH ion, Ally ein HOH "HOH Cro 2. (abe) Red Pil st strong reducing agent, 6 (aed) Beth are not mimor image of each other They difer in ‘configuration erse C1, Bath donot contain plane ofsymmety. 1 60) Stor °° 0 by Gaon Gu oH Hs (Chow) HOH Ge Ct;—ont hy —0H 3 - . ¥ ie os a fon HoH (cHiow), (CHO, x01 Guo 8. (Gb) Glucosoand fructose aremonosnccharie 10, (es) Canesugsrand mals ony erolysisgivetwomonosacharide, 15, (ab) Mutarotton sexibitedby monosaccharide. 18 (at) Compounds having nly one-COOH and Nip groups act as neta ‘min ac 276 Ht & Solution of Advanced Problems in Organi Chemitry if 1

    203 + 00, 211+ CO —> Cu 0 2) Lantlgoestestisused ordetectionof N Sand. 4. (© TMyPOg+ 12 @884Q MoO +21 HNO; 7 TF eattgs Poy 126003 +21 NHNOS + 12 #40 Hy © Be 1x 3D 503 Ee Sout map a o ® © - @) B rn 15, 16, 1, a, 2 o © o © © Hine & Solutions of Advanced Problems in Orgote Chemistry No: HO. 6-6, Lag OG [NaHCO reaction withbighly ci groups like. ‘Aromatic amine give couping reaction wth napa FeCly reacts wih phenal.Idoesnotreactwith aeahob. 2ndeompound doesnot contain COON group. (Only amin give carb aminereaction. Fling solution doesnoteactwtharomatialdehyde, anvave Lc on ony a Oe Ona ean Oe® ‘Reaction with Bry—H0 indicates presence of alkene and reaction ‘wah FeCl ndeae presence of phenol ‘Compound containing Cand tothe Lassigne'stet. = 2! a Ea (be) (does not contain benzylic hydrogen $0, oxidation dos ner se og tty BA Ga oe Bor ™ =a ee: cc aL alae cu a AL dl ou Me Aw Bt 8 x nus @ ‘Aromatic dehyde does wt reac wth Fb rere eee ET (abod) Allcontinhighly ciichy rope, (4) Only amines pivecarbylaminerecton, Ged) Allythaldesdo not reset with KMn0,, aed) ellen regent does noteeact witlketones, (abe) These compounds donot contain sp hybridise hydrogen. (abs) _Feblingsolton does notreact with amines, 20 Hines & Solution of Advanced Problems in Organic Chemiiry 15 bo) 1412 PASSAGE -2 Lo 2 © 3 @) Alcohols onotreactwit FeCl 1 15, 0. “ ‘Bosh contain —C—CH 50 give ier ration Nomenclature a KEKEE) SECTION-t 1. 2-eyanoathanoic ac 2, S-chloro-2-butmone 13. shloro-2-propanol 4. 2.beamobutanoleaid §, 3methoxybataal 6 13.pentadiene 7. Bromopropanone 8 1 4-buanediol 9. 4tydroxybuanoic acid 10, Methyl3-bromobwanoale 1. Stydroxypentanediocacis 12, S-butynenitie 2-€-ehlorosthy)>I-penene 14, Methy4methyl-3-oxopentanoste Sthexen2-0n¢ 16, Gamino--heptaral 2-tena) 18, 3-cloro-3-metylbaanal Propenoe ac 20, 22.2-tieloroethanoie acid 13.S-peatiene 22, 22-4imethyfpropanenitile DeshylLmetlyht-bulere 24, 2.22-stclor-, -thanedil #peaten-2-01 26, 4 peaten-290-1a1 2isopopy-3.3,3-dimethylbuy +1 4-penadiene 22-imethyl-t-buanel 28, |-chloro-4-methony2-buano 2methyl-24-pentanediol ——-M, 4-hydrny-2-methynentan Ahydromypentnoicacld 33, Smety/-hexenoi acid 2pentenoi acid 35, 3.amino-Sbeptnci acid Scer-buyl3,Snonanediol 37. 34 hydroxyetyS-methyIheptanal “4-bromo-2-thyeyelopentnone 6 romo-2-oxoeyclohexancurbaldehyde S-eyelohexene-12-eaboryic acid Celobupletanoleacld 2, A-hlo-2-meshy pentane “Mathy--brome-2-hydroxy-2-methyoutanoate 3 -amino-2-se-buy-S.cylohexen- 3 -crbory-3.ydroxypentanedeaoxyle ald 2medylSeren--ynole acid 47. |-chloro2,3-uanedil Butenediole sek 49, 2rome-2-methy3-cylopetefione 2m Hints & Solutions of Advanced Problems in Organic Chemistry | Nomenctanre 2 $0, Ditybunedonte | i ‘ 98. tomo 3-pentatone 99, 223-rietyL-penael | Be rome neveaeete 100, ano tie 101, engo-t0l Ef scmeeatnan = al 102,123 gropanetio 103, 23-neiy2-tuene ae ee 104,24 2-penteoe i108, 23-penanedione 6, 45ichor2-¢-crehydoxymetys-oxohe | Gyashexne Fenton 106. ytroxy2-peneoi aid 107. hlroprpanal Tepe | 23 pein t09, 1 stepatendyn6 os 1M, 2eblrpropanic aed 58, 3,3-4ny bi (epeneon) propa cd Me. 112eteroatane | 98, benzene. Svacte ald 6, Bcyl [4.20 octane 12. 2hlo-13-uiene 1B, methyl Spent | 61, 4-oxobutanoie acid or 3-ormylpropanoi acid W-phenylethanamide 115. N3.3-trimethylbatnamide | @ d.methoxyeatbonyl but 2-1-0 acid ‘SECTION - 11 |. soxobutanoic acid | 2 CyH,OCHCH,OH 64, 2amino--hydrony-t-oropenanoic acid (65, Numethy-2(2

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