A) 3-hexanone
B) 2, 4-hexanedione
C) 2, 5-hexanedione
D) 2, 3-hexanedione
Correct Answer: B
Solution :
2, 4-hexanedione (a 1, 3-diketone) has the most acidic hydrogen. This is because the carbanion left after the removal of \[{{H}^{+}}\] is resonance stabilised in this case. \[\underset{2,\,4-\text{Hexanedione}}{\mathop{C{{H}_{3}}-\overset{O}{\mathop{\overset{||}{\mathop{C}}\,}}\,-C{{H}_{2}}-\overset{O}{\mathop{\overset{||}{\mathop{C}}\,}}\,-C{{H}_{2}}C{{H}_{3}}}}\,\underset{-{{H}_{2}}O}{\mathop{\xrightarrow{O{{H}^{-}}}}}\,\]\[C{{H}_{3}}-\overset{O}{\mathop{\overset{||}{\mathop{C}}\,}}\,\,-\overset{-}{\mathop{C}}\,H-\overset{O}{\mathop{\overset{||}{\mathop{C}}\,}}\,-C{{H}_{2}}C{{H}_{3}}\] \[C{{H}_{3}}-\overset{O}{\mathop{\overset{||}{\mathop{C}}\,}}\,-\overset{-}{\mathop{C}}\,H-\overset{O}{\mathop{\overset{||}{\mathop{C}}\,}}\,-C{{H}_{2}}C{{H}_{3}}\]\[\leftrightarrow C{{H}_{3}}-\overset{{{O}^{-}}}{\mathop{\overset{|\,\,\,\,}{\mathop{C\,\,}}\,}}\,=CH-\overset{O}{\mathop{\overset{||}{\mathop{C}}\,}}\,-C{{H}_{2}}C{{H}_{3}}\] \[\leftrightarrow C{{H}_{3}}-\overset{O\,\,}{\mathop{\overset{||\,\,\,\,}{\mathop{C\,\,}}\,}}\,-CH=\overset{{{O}^{-}}}{\mathop{\overset{|\,\,\,\,}{\mathop{C\,\,}}\,}}\,-C{{H}_{2}}C{{H}_{3}}\]
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