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JEE Mains · Chemistry · STD 12 - 7. Alcohol, phenol and ethers

Two compounds \(A\) and \(B\) with same molecular formula \(\left( C _{3} H _{6} O \right)\) undergo Grignard's reaction with methylmagnesium bromide to give products \(C\) and \(D\). products \(C\) and \(D\) show following chemical tests.
Test \(C\) \(D\)
Ceric ammonium nitrate Test Positive positive
Lucas Test Turbidity obtained after five minutes Turbidity obtained immediately
Iodoform Test Positive Negative
\(C\) and \(D\) respectively are 

  1. A \(C = {H_3}C - \begin{array}{*{20}{c}} {C{H_3}\,\,\,\,\,\,\,\,} \\ |\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\ {C - OH} \\ |\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\ {C{H_3\,\,\,\,\,\,\,\,}} \end{array}\) \(\begin{array}{*{20}{c}} {D = {H_3}C - C{H_2} - CH - C{H_3}} \\ {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|} \\ {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,OH} \end{array}\)
  2. B \(C = H _{3} C - CH _{2}- C H _{2}- CH _{2}- OH\) \(D = {H_3}C - \begin{array}{*{20}{c}} {C{H_3}\,\,\,\,\,} \\ |\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\ {C - OH} \\ |\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\ {C{H_3}\,\,\,\,\,} \end{array}\)
  3. C \(\begin{array}{*{20}{c}} {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,OH} \\ {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|} \\ {C = {H_3}C - C{H_2} - CH - C{H_3}} \end{array}\) \(D = {H_3}C - \begin{array}{*{20}{c}} {C{H_3}\,\,\,\,\,} \\ |\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\ {C - OH} \\ |\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\ {C{H_3}\,\,\,\,\,} \end{array}\)
  4. D \(C = H _{3} C - CH _{2}- CH _{2}- CH _{2}- OH\) \(\begin{array}{*{20}{c}} {D = {H_3}C - C{H_2} - CH - C{H_3}} \\ {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|} \\ {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,OH} \end{array}\)
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Correct Answer

(C) \(\begin{array}{*{20}{c}} {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,OH} \\ {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|} \\ {C = {H_3}C - C{H_2} - CH - C{H_3}} \end{array}\) \(D = {H_3}C - \begin{array}{*{20}{c}} {C{H_3}\,\,\,\,\,} \\ |\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\ {C - OH} \\ |\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\ {C{H_3}\,\,\,\,\,} \end{array}\)

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\(\begin{array}{*{20}{c}} {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,O} \\ {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,||} \\ {C{H_3}C - C{H_2} - C - H} \\ {(A)} \end{array}\) \(\xrightarrow{CH_3MgBr}\)…
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