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JEE Advance 2008
paper 2
Question
In the following reaction sequence, the correct structures of E, F and G are
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Select the correct option:
A
(A) $\mathrm{E}=$ CC(=O)C1=CC=CC=C1 CC(=O)C1=CC=CC=C1 |(1.44402,-0.746078,;-0.0481341,0.120335,;-0.0962681,1.37182,;-1.29962,-0.746078,;-1.17684,-2.24104,;-2.41013,-3.09486,;-3.7662,-2.45371,;-3.88898,-0.958741,;-2.65569,-0.104926,)| RDKit 2D 0 0 0 0 0 0 0 0 0 0999 V3000 M V30 BEGIN CTAB M V30 COUNTS 9 9 0 0 0 M V30 BEGIN ATOM M V30 1 O -0.096268 1.371821 0.000000 0 M V30 2 C 1.444022 -0.746078 0.000000 0 M V30 3 C -0.048134 0.120335 0.000000 0 M V30 4 C -1.299620 -0.746078 0.000000 0 M V30 5 C -1.176838 -2.241044 0.000000 0 M V30 6 C -2.410127 -3.094859 0.000000 0 M V30 7 C -3.766196 -2.453708 0.000000 0 M V30 8 C -3.888977 -0.958741 0.000000 0 M V30 9 C -2.655689 -0.104926 0.000000 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 1 3 4 M V30 2 2 3 1 M V30 3 1 2 3 M V30 4 2 4 5 M V30 5 1 5 6 M V30 6 2 6 7 M V30 7 1 7 8 M V30 8 2 8 9 M V30 9 1 9 4 M V30 END BOND M V30 END CTAB M END InChI=1S/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H3 KWOLFJPFCHCOCG-UHFFFAOYSA-N F = *C(=O)C1=CC=CC=C1 *C(=O)C1=CC=CC=C1 |(1.57833,-0.60617,;-0.0686231,0.0800602,;-0.16012,1.26953,;-1.34959,-0.743416,;-1.27801,-2.24171,;-2.53977,-3.05284,;-3.87312,-2.36569,;-3.9447,-0.867398,;-2.68294,-0.0562617,),$O-Na+;;;;;;;;$,atomProp:0.molFileAlias.O-Na+| RDKit 2D 0 0 0 0 0 0 0 0 0 0999 V3000 M V30 BEGIN CTAB M V30 COUNTS 9 9 0 0 0 M V30 BEGIN ATOM M V30 1 C -1.349587 -0.743416 0.000000 0 M V30 2 R 1.578330 -0.606170 0.000000 0 M V30 3 C -0.068623 0.080060 0.000000 0 M V30 4 O -0.160120 1.269527 0.000000 0 M V30 5 C -1.278006 -2.241708 0.000000 0 M V30 6 C -2.539774 -3.052844 0.000000 0 M V30 7 C -3.873122 -2.365689 0.000000 0 M V30 8 C -3.944703 -0.867398 0.000000 0 M V30 9 C -2.682935 -0.056262 0.000000 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 1 3 1 M V30 2 2 3 4 M V30 3 1 2 3 M V30 4 2 1 5 M V30 5 1 5 6 M V30 6 2 6 7 M V30 7 1 7 8 M V30 8 2 8 9 M V30 9 1 9 1 M V30 END BOND M V30 END CTAB M END $\mathrm{G}=\mathrm{CHI}_3$
B
(B) $\mathrm{E}=$ CC(=O)C1=CC=CC=C1 CC(=O)C1=CC=CC=C1 |(1.41611,-0.756061,;-0.0240019,0.108009,;-0.0240019,1.35611,;-1.36811,-0.708057,;-1.33503,-2.20769,;-2.61721,-2.98616,;-3.93247,-2.26499,;-3.96556,-0.765357,;-2.68337,0.0131105,)| RDKit 2D 0 0 0 0 0 0 0 0 0 0999 V3000 M V30 BEGIN CTAB M V30 COUNTS 9 9 0 0 0 M V30 BEGIN ATOM M V30 1 C -0.024002 0.108009 0.000000 0 M V30 2 C -1.368111 -0.708057 0.000000 0 M V30 3 C 1.416115 -0.756061 0.000000 0 M V30 4 O -0.024002 1.356110 0.000000 0 M V30 5 C -1.335029 -2.207693 0.000000 0 M V30 6 C -2.617211 -2.986160 0.000000 0 M V30 7 C -3.932474 -2.264992 0.000000 0 M V30 8 C -3.965555 -0.765357 0.000000 0 M V30 9 C -2.683374 0.013110 0.000000 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 1 1 2 M V30 2 2 1 4 M V30 3 1 3 1 M V30 4 2 2 5 M V30 5 1 5 6 M V30 6 2 6 7 M V30 7 1 7 8 M V30 8 2 8 9 M V30 9 1 9 2 M V30 END BOND M V30 END CTAB M END InChI=1S/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H3 KWOLFJPFCHCOCG-UHFFFAOYSA-N $F=$ [*-]C(=O)C1=CC=CC=C1 [*-]C(=O)C1=CC=CC=C1 |(1.60151,-0.656735,;-0.195868,0.0806516,;-0.103695,1.2789,;-1.30195,-0.702821,;-1.1631,-2.19638,;-2.38714,-3.06341,;-3.75002,-2.43687,;-3.88887,-0.943313,;-2.66483,-0.0762874,),$O-Na+;;;;;;;;$,atomProp:0.molFileAlias.O-Na+| RDKit 2D 0 0 0 0 0 0 0 0 0 0999 V3000 M V30 BEGIN CTAB M V30 COUNTS 9 9 0 0 0 M V30 BEGIN ATOM M V30 1 O -0.103695 1.278904 0.000000 0 M V30 2 C -1.301948 -0.702821 0.000000 0 M V30 3 C -0.195868 0.080652 0.000000 0 M V30 4 R 1.601511 -0.656735 0.000000 0 CHG=-1 M V30 5 C -1.163100 -2.196381 0.000000 0 M V30 6 C -2.387136 -3.063407 0.000000 0 M V30 7 C -3.750021 -2.436873 0.000000 0 M V30 8 C -3.888869 -0.943313 0.000000 0 M V30 9 C -2.664833 -0.076287 0.000000 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 3 1 M V30 2 1 3 2 M V30 3 1 4 3 M V30 4 2 2 5 M V30 5 1 5 6 M V30 6 2 6 7 M V30 7 1 7 8 M V30 8 2 8 9 M V30 9 1 9 2 M V30 END BOND M V30 END CTAB M END $\mathrm{G}=\mathrm{CHI}_3$
C
(C) $\mathrm{E}=$ CC(=O)C1=CC=CC=C1 CC(=O)C1=CC=CC=C1 |(1.43615,-0.777915,;-0.0478717,0.131647,;-0.0957433,1.37631,;-1.29254,-0.730043,;-1.16975,-2.22501,;-2.40304,-3.07882,;-3.75911,-2.43767,;-3.88189,-0.942706,;-2.6486,-0.0888915,)| RDKit 2D 0 0 0 0 0 0 0 0 0 0999 V3000 M V30 BEGIN CTAB M V30 COUNTS 9 9 0 0 0 M V30 BEGIN ATOM M V30 1 O -0.095743 1.376310 0.000000 0 M V30 2 C 1.436150 -0.777915 0.000000 0 M V30 3 C -1.292535 -0.730043 0.000000 0 M V30 4 C -0.047872 0.131647 0.000000 0 M V30 5 C -1.169754 -2.225009 0.000000 0 M V30 6 C -2.403042 -3.078824 0.000000 0 M V30 7 C -3.759112 -2.437673 0.000000 0 M V30 8 C -3.881893 -0.942706 0.000000 0 M V30 9 C -2.648605 -0.088891 0.000000 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 4 1 M V30 2 1 4 3 M V30 3 1 2 4 M V30 4 2 3 5 M V30 5 1 5 6 M V30 6 2 6 7 M V30 7 1 7 8 M V30 8 2 8 9 M V30 9 1 9 3 M V30 END BOND M V30 END CTAB M END InChI=1S/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H3 KWOLFJPFCHCOCG-UHFFFAOYSA-N F = [*-]C(=O)C1=CC=CC=C1 [*-]C(=O)C1=CC=CC=C1 |(1.62655,-0.62125,;-0.0903637,0.101659,;-0.180727,1.2312,;-1.35545,-0.711614,;-1.28387,-2.2099,;-2.54564,-3.02104,;-3.87899,-2.33389,;-3.95057,-0.835595,;-2.6888,-0.0244591,),$O-Na+;;;;;;;;$,atomProp:0.molFileAlias.O-Na+| RDKit 2D 0 0 0 0 0 0 0 0 0 0999 V3000 M V30 BEGIN CTAB M V30 COUNTS 9 9 0 0 0 M V30 BEGIN ATOM M V30 1 C -1.355455 -0.711614 0.000000 0 M V30 2 R 1.626546 -0.621250 0.000000 0 CHG=-1 M V30 3 O -0.180727 1.231205 0.000000 0 M V30 4 C -0.090364 0.101659 0.000000 0 M V30 5 C -1.283874 -2.209905 0.000000 0 M V30 6 C -2.545642 -3.021041 0.000000 0 M V30 7 C -3.878990 -2.333887 0.000000 0 M V30 8 C -3.950571 -0.835595 0.000000 0 M V30 9 C -2.688803 -0.024459 0.000000 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 1 4 1 M V30 2 2 4 3 M V30 3 1 2 4 M V30 4 2 1 5 M V30 5 1 5 6 M V30 6 2 6 7 M V30 7 1 7 8 M V30 8 2 8 9 M V30 9 1 9 1 M V30 END BOND M V30 END CTAB M END $\mathrm{G}=\stackrel{*}{\mathrm{C}} \mathrm{HI}_3$
D
(D) $E=$ CC(=O)C1=CC=CC=C1 CC(=O)C1=CC=CC=C1 |(1.44663,-0.771534,;-0.0964417,0.0964417,;0,1.35018,;-1.35018,-0.675092,;-1.30811,-2.1745,;-2.58559,-2.96065,;-3.90516,-2.24738,;-3.94724,-0.747975,;-2.66975,0.0381715,)| RDKit 2D 0 0 0 0 0 0 0 0 0 0999 V3000 M V30 BEGIN CTAB M V30 COUNTS 9 9 0 0 0 M V30 BEGIN ATOM M V30 1 C -0.096442 0.096442 0.000000 0 M V30 2 C -1.350184 -0.675092 0.000000 0 M V30 3 O 0.000000 1.350184 0.000000 0 M V30 4 C 1.446626 -0.771534 0.000000 0 M V30 5 C -1.308105 -2.174502 0.000000 0 M V30 6 C -2.585593 -2.960648 0.000000 0 M V30 7 C -3.905159 -2.247384 0.000000 0 M V30 8 C -3.947238 -0.747975 0.000000 0 M V30 9 C -2.669750 0.038171 0.000000 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 1 3 M V30 2 1 4 1 M V30 3 1 1 2 M V30 4 2 2 5 M V30 5 1 5 6 M V30 6 2 6 7 M V30 7 1 7 8 M V30 8 2 8 9 M V30 9 1 9 2 M V30 END BOND M V30 END CTAB M END InChI=1S/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H3 KWOLFJPFCHCOCG-UHFFFAOYSA-N F = *C(=O)C1=CC=CC=C1 *C(=O)C1=CC=CC=C1 |(1.6147,-0.629847,;-0.125969,0.0572588,;-0.125969,1.24824,;-1.36276,-0.675654,;-1.34573,-2.17556,;-2.63616,-2.94026,;-3.94363,-2.20506,;-3.96067,-0.705158,;-2.67023,0.0595454,),$O-Na+;;;;;;;;$,atomProp:0.molFileAlias.O-Na+| RDKit 2D 0 0 0 0 0 0 0 0 0 0999 V3000 M V30 BEGIN CTAB M V30 COUNTS 9 9 0 0 0 M V30 BEGIN ATOM M V30 1 C -1.362760 -0.675654 0.000000 0 M V30 2 C -0.125969 0.057259 0.000000 0 M V30 3 R 1.614699 -0.629847 0.000000 0 M V30 4 O -0.125969 1.248243 0.000000 0 M V30 5 C -1.345726 -2.175558 0.000000 0 M V30 6 C -2.636164 -2.940261 0.000000 0 M V30 7 C -3.943635 -2.205061 0.000000 0 M V30 8 C -3.960669 -0.705158 0.000000 0 M V30 9 C -2.670232 0.059545 0.000000 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 1 2 1 M V30 2 2 2 4 M V30 3 1 3 2 M V30 4 2 1 5 M V30 5 1 5 6 M V30 6 2 6 7 M V30 7 1 7 8 M V30 8 2 8 9 M V30 9 1 9 1 M V30 END BOND M V30 END CTAB M END $\mathrm{G}=\dot{\mathrm{C}} \mathrm{H}_3 \mathrm{I}$
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