Hydrocarbons 2 Question 55

59. (a) Identify $(A),(B),(C),(D)$ and $(E)$ in the following schemes and write their structures :

(b) Identify $(X),(Y)$ and $(Z)$ in the following synthetic scheme and write their structures. Explain the formation of labelled formaldehyde $\left(\mathrm{H}{2} \mathrm{C}^{} \mathrm{O}\right)$ as one of the products when compound $(Z)$ is treated with $\mathrm{HBr}$ and subsequently ozonolysed. Mark the $\mathrm{C}^{}$ carbon in the entire scheme. $\mathrm{BaC}^{*} \mathrm{O}{3}+\mathrm{H}{2} \mathrm{SO}{4} \rightarrow(X)$ gas

$\left[\mathrm{C}^{*}\right.$ denotes $\mathrm{C}^{14}$ ]

$$ \mathrm{H}{2} \mathrm{C}=\mathrm{CH}-\mathrm{Br} \xrightarrow[\substack{\text { (ii) } X \ \text { (iii) } \mathrm{H}{3} \mathrm{O}^{+}}]{\text {(i) Mg/ether }}(Y) \xrightarrow{\mathrm{LiAlH}_{4}}(Z) $$

(2001)

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Solution:

(a)

(b) $\mathrm{BaCO}{3}+\mathrm{H}{2} \mathrm{SO}{4} \longrightarrow \stackrel{*}{\mathrm{CO}{2}}+\mathrm{BaSO}_{4}$