1. Tardigrade
  2. Question
  3. Chemistry
  4. A compound A having the molecular formula C5H12O, on oxidation gives a compound B with molecular formula C5H10O . Compound B give a 2, 4-dinitrophenylhydrazine derivative but did not answer haloform test or silver mirror test. The structure of compound A is

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Q. A compound A having the molecular formula $ {{C}_{5}}{{H}_{12}}O, $ on oxidation gives a compound B with molecular formula $ {{C}_{5}}{{H}_{10}}O\,. $ Compound B give a 2, 4-dinitrophenylhydrazine derivative but did not answer haloform test or silver mirror test. The structure of compound A is

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Solution:

Since, the compound B gave a 2, 4-dinitrophenylhydrazine derivative but did not answer halo form test or silver mirror test, it must contains $ a>C=O $ group, but it is neither a methyl ketone nor an aldehyde. Moreover, compound B is obtained by the oxidation of compound A, having molecular formula $ {{C}_{5}}{{H}_{12}}O, $ so the compound A must be a secondary alcohol. Thus. A is $ \underset{(secondary\,alcohol)}{\mathop{C{{H}_{3}}C{{H}_{2}}-\underset{OH}{\mathop{\underset{\mathbf{|}}{\mathop{CH}}\,}}\,-C{{H}_{2}}-C{{H}_{3}}}}\,\xrightarrow[-\,{{H}_{2}}O]{[O]} $ $ \underset{\begin{smallmatrix} (do\,not\,answer\,haloform\, \\ test\,or\,silver\,mirror\,test) \end{smallmatrix}}{\mathop{C{{H}_{3}}C{{H}_{2}}\overset{O}{\mathop{\overset{\mathbf{||}}{\mathop{C}}\,}}\,-C{{H}_{2}}C{{H}_{3}}}}\, $