Aldehydes and Ketones - Result Question 52
####62. 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.
$(2001,5 M)$
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Solution:
- $B+NaOH / I _2 \longrightarrow C _6 H _5 COONa+CHI _3$
