First slide
Aliphatic aldehydes and ketones
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 Br2H2O . 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 ZnH2O 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.

Moderate
Question

Which of the following statement regarding A and B is correct?

Solution

Both A and B are alcohols with one degree of unsaturation but none of them decolourise Br2H2O solution, hence they are cyclic.

A  or  BΔConc.  H2SO4C7H12CZn/H2OO3C7H12O2DNaBH4C7H16O2E

E has only one methyl group and gives iodoform test hence, E may be 

CH3CHCH2CH2CH2CH2CH2OH                            |                         OH

(B) A has a chiral carbon but B does not.

 

 

Question

Which of the following statement regarding A and B is incorrect?

Solution

Both A and B are alcohols with one degree of unsaturation but none of them decolourise Br2H2O solution, hence they are cyclic.

A  or  BΔConc.  H2SO4C7H12CZn/H2OO3C7H12O2DNaBH4C7H16O2E

E has only one methyl group and gives iodoform test hence, E may be 

CH3CHCH2CH2CH2CH2CH2OH                            |                         OH

(D) B is a tertiary alcohol, does not react with SOCl2.

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