A and B are two structural isomers with their molecular formula C7H14O and both gives-off effervescence on heating with Na-metal. However, neither A nor B decolourise brown colour of Br2−H2O . Treating either A or B with hot conc. sulphuric acid solution results in the formation of the same compound C (C7H12).C on treatment with O3 followed by Zn−H2O gives D (C7H12O2). D gives E(C7H16O2) on treatment with NaBH4. E has only one methyl group and forms yellow ppt. with I2/KOH. Also, A gives delayed turbidity on treatment with conc. HCl/ZnCl2 while B gives immediate turbidity on similar treatment.

Question

A and B are two structural isomers with their molecular formula C7H14O and both gives-off effervescence on heating with Na-metal. However, neither A nor B decolourise brown colour of Br2−H2O . Treating either A or B with hot conc. sulphuric acid solution results in the formation of the same compound  C (C7H12).C  on treatment with O3 followed by Zn−H2O gives D (C7H12O2). D gives E(C7H16O2) on treatment with NaBH4.  E has only one methyl group and forms yellow ppt. with I2/KOH. Also, A gives delayed turbidity on treatment with conc. HCl/ZnCl2 while B gives immediate turbidity on similar treatment.

Accepted Answer

Both A and B are alcohols with one degree of unsaturation but none of them decolourise Br2−H2O solution, hence they are cyclic.A  or  B→ΔConc.  H2SO4C7H12C→Zn/H2OO3C7H12O2D→NaBH4C7H16O2EE has only one methyl group and gives iodoform test hence, E may be CH3−CH−CH2CH2CH2CH2CH2OH                            |                         OH(B) A has a chiral carbon but B does not.

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