Hydrocarbons - Result Question 73
####60. An alkene $(A) C _{16} H _{16}$ on ozonolysis gives only one product $(B) C _8 H _8 O$. Compound $(B)$ on reaction with $NaOH / I _2$ yields sodium benzoate. Compound $(B)$ reacts with $KOH / NH _2 NH _2$ yielding a hydrocarbon $(C) C _8 H _{10}$. Write the structures of compounds $(B)$ and $(C)$. Based on this information two isomeric structures can be proposed for alkene $(A)$. Write their structures and identify the isomer which on catalytic hydrogenation $\left(H _2 / Pd-C\right)$ gives a racemic mixture.
(2001)
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Solution:
- $B+NaOH+I _2 \longrightarrow C _6 H _5-COONa$ (Iodoform reaction)
$\therefore B$ is $C _6 H _5-\stackrel{O}{C}-CH _3$
$B+N _2 H _4 \xrightarrow{KOH}$ Hydrocarbon $(C)$ “Wolff-Kishner Reduction”
$\therefore C$ is $C _6 H _5-CH _2-CH _3$
Hence, $A$ can be one of the following :
I on catalytic hydrogenation, would give meso compound while II on catalytic hydrogenation, would produce racemic mixtures.
