Question

An alkene A with molecular formula C₅H₁₀ on ozonolysis gives a mixture of two compounds B and C. Compound B gives positive Fehling test and also reacts with iodine and NaOH solution. Compound C does not give Fehling solution test but forms iodoform. Identity the compounds A, B and C.

Answer 1

\[\begin{array}{cc}
\ce{CH3CH=C-CH3->[(i) O3][(ii) Zn/H2O]\underset{(B)}{CH3CHO} + CH3-C-CH3}\\
\phantom{......}|\phantom{.........................................................}||\\
\ce{\phantom{......}\underset{(A)}{CH3}}\phantom{....................................................}\ce{\underset{(C)}{O}}\\
\end{array}\]

\[\ce{\underset{(B)}{CH3CHO} + 3I2 + 4NaOH ->HCOONa + CHI3 + 3NaI + 3H2O}\]

\[\ce{\underset{(C)}{CH3COCH3} + 4NaOH + 3I2 ->CHI3 + 3NaI + 3H2O + CH3COONa}\]