38. sol. sol. The reaction between X and ¥ to give Z proceeds via Po D fy A te t x y fa) 4% ~ conretatory opening of X followed by endo Diels ~ Alder cycloadcition. (4K — alertatry opening of Fellowes by endo Dats = Alder yeoaeton (014 ~ contatry opening of olowed by ex Dale Aldar eyeloadeition. (6) 4k — dicrotatory opening of X fellowed by exo Dials ~ Alder cycloaddition. @ o 2— Mca oe n oO ll endo) Pa Correct option Is (a) Photoirradiation leads to the following set of products: ° + HyC—CH, ° @’ LI) + Pw @ ° Ang ey, ti, mH eg. a : Fao yey, + HC me eysiation it Ph: Correct option is (¢) Linked Answer Q. 82 and Q. 83 In the following reaction, 28 3)40. The products ¥ and Z are formed, respectively, from X via Ans. sol. 43. 3 abv ponrsmnny opernngania Ar wareeerny open (©) ND. cisrorstory opaning and 4. conrotstory opening (©)4. conrotatory opening and '™. gisrotatory opening. (@y Aranasesteapapanmpana bx conraetary opanine @ D oH (yy w | (Con) D ‘ = H @ on Conteet option is (a) > ‘The photochemical reaction of 2 ~ methylpropane with Fo gives 2 ~ fluoro ~ 2 - methylpropane and 1 - fluoro - 2 - methylpropane in 14:86 ratio. The corresponding ratio of the bromo products in the above reaction using Br2 Is most likely to be Ans. Sol. (14:86 (6) 50: 50 wus (6) 99:1 @ Br-Br wrt cH Se aA HyC™ CH) = amore sable ‘aca on cH, selective So, reacts wil move fi stable free radial newScH, nc o9%e Ratlo between 2-broma~ Carrect-option is (3) methyl propane and 1-brome-2-methyl propane is 92:182. Ans. sol. Ane. sol. ‘The reactive intermediate | and the product P are carbene and H aid 2A @) ®) eaubene ail 23 AA go saibene mid 2 2 taidcal and PrWg @ (a) Product [P] —= H H Corréct option is (2) In the photochemical reaction co tne NY Meo" ‘Me wos" formation of the compound X can be inferred by the disappearance of the 'H NMR signal at 'H NMR spectrum ef the starting material 397 (1H. 9), 78 (Hd. J = 80 He), 71-68 2H.) 3.9 GH. 9). 2.838. ») pia) g@ 597 ppm 878 PPm fe) 839 ppm 529 Pom ) ° 1 Oe ae HO oD Meo" Me Tho ;00 Meo! Me The signal of ~CHO proton disappear at 87 ppm Correct option is (2)22. The pericyclic reaction given below is an example of w- Ny ag a+ AY so) <3 i (@) ft, 3] — sigmatropic shift (b) [1, 8) — sigmatropic shift (© [3, 5] - sigmatropie shift (a) (3, 3] — sigmatropic shift Ans. (A) Sol. It is an example of 3, 3-sigmatropic shift. Correct option is (4) 32. Match the compound in the Column ~ | with photochemical reactions that they can undergo given in the Column — I: Column —1 Column — tt (p) oxa ~ di~ = ~ methane rearrangement (q) Patemo ~ Buchi reaction (0) intramolecular {2 + 2] ~ cycloaddition (6) photoenolation @) @ - @: Gi) - ©: Gi) -@ (b) (1) - (3 Gi) - (PGi) - ©) (©) @ - (P) Gi) - © Gil) - @) ) () — 5 - @; (i) - 8) Ans. (b)21. Formation of the product in the following photochemical reaction involves (a) di-t-methine: rearrangement (0) Paterno-Buchi reaction (©) 2, 3}-sigmatropic rearrangement (d) Norrish type | reaction Ans. (a) Sol. © oe Asahi oa Pho Ph teapenr Correct option is (a) 49. The major product X and Y formed in the following reaction sequence are ci ntene > EY “oe @ (b)51. The major product formed in the following reaction ep Seon _heat py Ph @ Ans. (©) Pi mse Sol. Correct answer is (c) 55. The m/z value of the detectable fragment formed by McLafferty like rearrangement of the following compound in mass spectrometer is Ans. (41) 4 41 (odd mass) spectroscopy sol. as(41 10.41) Correct option is (41)1. Amongst the following the compound that DOES NOT act as a diene in Diels-Alder reaction is Ans. (b) —— This dienes in wasoid forn and does not give Diels-Alder reaction Sol. Correct option is (b) ‘3s. Ihe major product tormed in the Tollowing reaction 1s Me Me a ‘Me Me O., ® te Me U “te © M Me ite o aye ly ‘Me w he ans. (®) Me a= Gn21. The major product obtained in the following reaction, is SS Set (es sensitize) —~ | | @ (b) (1 ) ss (d) 7 Ans. (d) sol. 2 Ss be + AN = = GH Teme L Tas as sensitizer ce (Dimerization reaction) 22. Inthe two setp reaction sequence given below, the starting bis - sulfone acts as s0.Ph O-e" = &, me, of - “hon” ‘SOsPh SOsPh ‘heat SOPh (2) a dienophile and synthetic equivalent of acetylene (b).a dienophite and synthetic equivaient of ethylene (©) a dipolaraphite and synthetic equivalent of acetylene (d) a dipolarophile and eynthetic equivalent of ethylene Ans. (a) OC b atte A "S0,Ph “EtOH heat SO:Pb (Diene) —_Dienophile Sol. Cyclo Addition (iene) Dienophile Acetylen Correct option is (a)2. ans. sot. 41. ans. ‘Tho major product formed in the following photochemical reaction is no aaa xo @ © No yw @ 0 © 4 AD te AA gi Silahanetion, erPra NO yo oa AK Wont BE AAA on thie fe Baton Reaction Correct option i (2) The product formed in the following photochet Me. Me i \ by Me Pi” Ph Ph. Me Ph4. The major product of the following intramolecular cycloaddition reaction is ‘cor ° @ (b) ro) A hy © ©. ° dd) Ans. (a) 9 40. The strongest band observed in the IR spectrum of the final product of the following reaction appears, approximately at 100 cm“ (Upto one decimal place) Hy ZA~on _s RACH. on ‘Ans. (17.0) > oy S y CH, Veen, au OH Correct answer is (170)17. The product(s) formed in the following reaction is(are) acowry amy cH, (@ 1 only (b) only (© only (@) Mixture of | and It Ans. ** F a ow Ss nen CH, Mechansinr Z wev — LE so. ——* E 19. The number of following diene(s) that undergo Diels-Alder reaction with methyl acrylate is OOO CKOCO LO oo tf Sol. ChoidDicne Cisoid Dene TrmoidDiene Cis olf Dene HAC. i wh O Trans oid Diene Cod Diene Cisoid Diene Correct answer is 5.55. The major product formed in the following reaction is 9 Lei ptyct Ho Stet a CH, @ a CH; (b) a CH, © al CH. oe Ans. (d) ¢ Exec Sol. be Correct option is (d) >, Ke, (ibjor)