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JEE Advance 2012
paper 2
Question
In the following reactions sequence, the compound J is an intermediate. $$ \text { I } \xrightarrow{\left(\mathrm{CH}_3 \mathrm{CO}\right)_2 \mathrm{O}} \text { J } \xrightarrow[\substack{\text { (ii) } \mathrm{SOCl}_2 \\ \text { (ii) anhyd. } \mathrm{AlCl}_3}]{\text { (i) } \mathrm{H}_2, \mathrm{Pd} / \mathrm{C}} \mathrm{~K} $$ $\mathrm{J}\left(\mathrm{C}_9 \mathrm{H}_8 \mathrm{O}_2\right)$ gives effervescence on treatment with $\mathrm{NaHCO}_3$ and positive Baeyer's test
The compound I is
Select the correct option:
A
[H]C(=O)C1=CC=CC=C1 [H]C(=O)C1=CC=CC=C1 |(1.41998,2.15338,;0.0156042,1.45119,;-1.52921,2.15338,;0.0156042,0.608565,;-1.38878,-0.234063,;-1.38878,-1.77888,;0.0156042,-2.34063,;1.41998,-1.77888,;1.41998,-0.234063,)| 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 1.419984 -0.234063 0.000000 0 M V30 2 O -1.529213 2.153382 0.000000 0 M V30 3 C 0.015604 0.608565 0.000000 0 M V30 4 H 1.419984 2.153382 0.000000 0 M V30 5 C 1.419984 -1.778881 0.000000 0 M V30 6 C -1.388775 -1.778881 0.000000 0 M V30 7 C 0.015604 1.451192 0.000000 0 M V30 8 C 0.015604 -2.340633 0.000000 0 M V30 9 C -1.388775 -0.234063 0.000000 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 3 9 M V30 2 1 6 9 M V30 3 1 5 8 M V30 4 2 7 2 M V30 5 1 1 3 M V30 6 1 7 4 M V30 7 2 8 6 M V30 8 1 3 7 M V30 9 2 5 1 M V30 END BOND M V30 END CTAB M END InChI=1S/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H HUMNYLRZRPPJDN-UHFFFAOYSA-N
B
OCC1=CC=CC=C1 OCC1=CC=CC=C1 |(1.57271,2.38499,;-0.224673,1.69369,;-0.224673,0.864126,;-1.60728,0.0345651,;-1.60728,-1.4863,;-0.224673,-2.03934,;1.15793,-1.4863,;1.15793,0.0345651,)| RDKit 2D 0 0 0 0 0 0 0 0 0 0999 V3000 M V30 BEGIN CTAB M V30 COUNTS 8 8 0 0 0 M V30 BEGIN ATOM M V30 1 C 1.157929 0.034565 0.000000 0 M V30 2 C -1.607275 0.034565 0.000000 0 M V30 3 O 1.572710 2.384989 0.000000 0 M V30 4 C -0.224673 0.864126 0.000000 0 M V30 5 C -1.607275 -1.486297 0.000000 0 M V30 6 C 1.157929 -1.486297 0.000000 0 M V30 7 C -0.224673 -2.039338 0.000000 0 M V30 8 C -0.224673 1.693688 0.000000 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 1 8 3 M V30 2 2 4 2 M V30 3 1 1 4 M V30 4 1 4 8 M V30 5 1 5 2 M V30 6 1 6 7 M V30 7 2 6 1 M V30 8 2 7 5 M V30 END BOND M V30 END CTAB M END InChI=1S/C7H8O/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2 WVDDGKGOMKODPV-UHFFFAOYSA-N
C
CC(=O)C1=CC=CC=C1 CC(=O)C1=CC=CC=C1 |(1.77356,1.97062,;0,1.3567,;-1.5007,2.17526,;0,0.538131,;-1.5007,-0.280434,;-1.5007,-1.64471,;0,-2.19042,;1.36427,-1.64471,;1.36427,-0.280434,)| 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 -1.500702 -0.280434 0.000000 0 M V30 2 C -1.500702 -1.644709 0.000000 0 M V30 3 C 1.364275 -1.644709 0.000000 0 M V30 4 C 0.000000 -2.190419 0.000000 0 M V30 5 C 0.000000 0.538131 0.000000 0 M V30 6 C 1.364275 -0.280434 0.000000 0 M V30 7 O -1.500702 2.175260 0.000000 0 M V30 8 C 0.000000 1.356695 0.000000 0 M V30 9 C 1.773557 1.970619 0.000000 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 8 7 M V30 2 1 5 8 M V30 3 2 5 1 M V30 4 1 6 5 M V30 5 1 2 1 M V30 6 2 3 6 M V30 7 2 4 2 M V30 8 1 8 9 M V30 9 1 3 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
D
[H]C([H])=C([H])C1=CC=CC=C1 [H]C([H])=C([H])C1=CC=CC=C1 |(1.93816,0.938262,;0.582133,1.69161,;1.48615,2.9723,;-0.321886,1.08893,;-1.75325,1.84228,;-0.321886,0.184913,;-1.82858,-0.719106,;-1.82858,-2.2258,;-0.321886,-2.82848,;1.18481,-2.2258,;1.18481,-0.719106,)| RDKit 2D 0 0 0 0 0 0 0 0 0 0999 V3000 M V30 BEGIN CTAB M V30 COUNTS 11 11 0 0 0 M V30 BEGIN ATOM M V30 1 C -0.321886 0.184913 0.000000 0 M V30 2 C 1.184813 -2.225804 0.000000 0 M V30 3 H 1.938162 0.938262 0.000000 0 M V30 4 H 1.486152 2.972305 0.000000 0 M V30 5 C 1.184813 -0.719106 0.000000 0 M V30 6 C -0.321886 -2.828483 0.000000 0 M V30 7 H -1.753249 1.842281 0.000000 0 M V30 8 C 0.582133 1.691611 0.000000 0 M V30 9 C -1.828584 -2.225804 0.000000 0 M V30 10 C -1.828584 -0.719106 0.000000 0 M V30 11 C -0.321886 1.088932 0.000000 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 1 2 6 M V30 2 1 1 11 M V30 3 2 6 9 M V30 4 1 3 8 M V30 5 1 9 10 M V30 6 2 2 5 M V30 7 1 11 7 M V30 8 2 8 11 M V30 9 1 8 4 M V30 10 2 1 10 M V30 11 1 5 1 M V30 END BOND M V30 END CTAB M END InChI=1S/C8H8/c1-2-8-6-4-3-5-7-8/h2-7H,1H2 PPBRXRYQALVLMV-UHFFFAOYSA-N
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