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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 K is
Select the correct option:
A
C1=CC2=C(C=C1)CCC2 C1=CC2=C(C=C1)CCC2 |(-2.29766,0.578028,;-0.867041,1.35836,;0.303464,0.578028,;0.303464,-0.592478,;-0.867041,-1.37282,;-2.29766,-0.592478,;1.47397,-1.37282,;2.77453,0.0578028,;1.47397,1.35836,)| RDKit 2D 0 0 0 0 0 0 0 0 0 0999 V3000 M V30 BEGIN CTAB M V30 COUNTS 9 10 0 0 0 M V30 BEGIN ATOM M V30 1 C 0.303464 -0.592478 0.000000 0 M V30 2 C 1.473970 -1.372816 0.000000 0 M V30 3 C 0.303464 0.578028 0.000000 0 M V30 4 C 1.473970 1.358365 0.000000 0 M V30 5 C -0.867041 1.358365 0.000000 0 M V30 6 C -0.867041 -1.372816 0.000000 0 M V30 7 C -2.297660 0.578028 0.000000 0 M V30 8 C 2.774532 0.057803 0.000000 0 M V30 9 C -2.297660 -0.592478 0.000000 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 1 8 4 M V30 2 2 1 3 M V30 3 1 4 3 M V30 4 2 6 9 M V30 5 2 5 7 M V30 6 1 3 5 M V30 7 1 9 7 M V30 8 1 6 1 M V30 9 1 2 1 M V30 10 1 2 8 M V30 END BOND M V30 END CTAB M END InChI=1S/C9H10/c1-2-5-9-7-3-6-8(9)4-1/h1-2,4-5H,3,6-7H2 PQNFLJBBNBOBRQ-UHFFFAOYSA-N
B
O=C1CCC2=C(C=CC=C2)O1 O=C1CCC2=C(C=CC=C2)O1 |(3.77759,-1.34163,;2.3494,-0.661542,;2.3494,0.970674,;0.989222,1.51475,;-0.370958,0.970674,;-0.370958,-0.661542,;-1.73114,-1.20561,;-3.09132,-0.661542,;-3.09132,0.698638,;-1.73114,1.51475,;0.921213,-1.1376,)| RDKit 2D 0 0 0 0 0 0 0 0 0 0999 V3000 M V30 BEGIN CTAB M V30 COUNTS 11 12 0 0 0 M V30 BEGIN ATOM M V30 1 C -0.370958 -0.661542 0.000000 0 M V30 2 C 0.989222 1.514746 0.000000 0 M V30 3 O 0.921213 -1.137605 0.000000 0 M V30 4 O 3.777590 -1.341632 0.000000 0 M V30 5 C -1.731138 1.514746 0.000000 0 M V30 6 C -1.731138 -1.205614 0.000000 0 M V30 7 C -0.370958 0.970674 0.000000 0 M V30 8 C 2.349401 0.970674 0.000000 0 M V30 9 C 2.349401 -0.661542 0.000000 0 M V30 10 C -3.091317 0.698638 0.000000 0 M V30 11 C -3.091317 -0.661542 0.000000 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 1 9 3 M V30 2 1 9 8 M V30 3 2 5 10 M V30 4 2 6 11 M V30 5 1 3 1 M V30 6 1 11 10 M V30 7 1 8 2 M V30 8 2 1 7 M V30 9 1 2 7 M V30 10 2 4 9 M V30 11 1 1 6 M V30 12 1 7 5 M V30 END BOND M V30 END CTAB M END InChI=1S/C9H8O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-4H,5-6H2 VMUXSMXIQBNMGZ-UHFFFAOYSA-N
C
O=C1CCC2=C1C=CC=C2 O=C1CCC2=C1C=CC=C2 |(2.15913,-2.34458,;1.36436,-1.01996,;2.55652,0.437125,;1.36436,1.49682,;0.0397386,0.966973,;0.0397386,-0.49011,;-1.15242,-1.01996,;-2.6095,-0.49011,;-2.6095,0.966973,;-1.15242,1.49682,)| RDKit 2D 0 0 0 0 0 0 0 0 0 0999 V3000 M V30 BEGIN CTAB M V30 COUNTS 10 11 0 0 0 M V30 BEGIN ATOM M V30 1 O 2.159132 -2.344579 0.000000 0 M V30 2 C 1.364360 1.496822 0.000000 0 M V30 3 C 0.039739 -0.490110 0.000000 0 M V30 4 C -2.609503 0.966973 0.000000 0 M V30 5 C 1.364360 -1.019958 0.000000 0 M V30 6 C -1.152420 -1.019958 0.000000 0 M V30 7 C -2.609503 -0.490110 0.000000 0 M V30 8 C 0.039739 0.966973 0.000000 0 M V30 9 C 2.556518 0.437125 0.000000 0 M V30 10 C -1.152420 1.496822 0.000000 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 1 9 2 M V30 2 1 2 8 M V30 3 1 6 3 M V30 4 2 6 7 M V30 5 1 5 9 M V30 6 1 5 3 M V30 7 1 7 4 M V30 8 2 3 8 M V30 9 1 8 10 M V30 10 2 1 5 M V30 11 2 10 4 M V30 END BOND M V30 END CTAB M END InChI=1S/C9H8O/c10-9-6-5-7-3-1-2-4-8(7)9/h1-4H,5-6H2 QNXSIUBBGPHDDE-UHFFFAOYSA-N
D
O=C1CC2=C(C=CC=C2)C1 O=C1CC2=C(C=CC=C2)C1 |(3.74314,0,;2.24588,0,;1.07412,-1.43216,;-0.097647,-0.65098,;-0.097647,0.781176,;-1.26941,1.30196,;-2.70157,0.781176,;-2.70157,-0.65098,;-1.26941,-1.43216,;1.07412,1.30196,)| RDKit 2D 0 0 0 0 0 0 0 0 0 0999 V3000 M V30 BEGIN CTAB M V30 COUNTS 10 11 0 0 0 M V30 BEGIN ATOM M V30 1 C 2.245881 0.000000 0.000000 0 M V30 2 C -2.701567 -0.650980 0.000000 0 M V30 3 C 1.074117 -1.432156 0.000000 0 M V30 4 C -0.097647 0.781176 0.000000 0 M V30 5 C -1.269411 1.301960 0.000000 0 M V30 6 C -0.097647 -0.650980 0.000000 0 M V30 7 C -2.701567 0.781176 0.000000 0 M V30 8 C -1.269411 -1.432156 0.000000 0 M V30 9 O 3.743136 0.000000 0.000000 0 M V30 10 C 1.074117 1.301960 0.000000 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 5 7 M V30 2 2 9 1 M V30 3 1 3 1 M V30 4 1 1 10 M V30 5 1 3 6 M V30 6 1 4 5 M V30 7 1 10 4 M V30 8 1 6 8 M V30 9 2 8 2 M V30 10 2 6 4 M V30 11 1 2 7 M V30 END BOND M V30 END CTAB M END InChI=1S/C9H8O/c10-9-5-7-3-1-2-4-8(7)6-9/h1-4H,5-6H2 UMJJFEIKYGFCAT-UHFFFAOYSA-N
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