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Q. Identify the alkyne in the following sequence of reactions,
Alkyne $\xrightarrow[\text{Lindlar's catalyst}]{H_2} A \xrightarrow{\text{Ozonolysis}} B only \xleftarrow[\text{Process}]{\text{Wacker}} CH_2 = CH_2$

BITSATBITSAT 2009

Solution:

In Wacker process, alkene is oxidised into aldehyde.
$ CH_2 = CH_2 + \frac{1}{2} \xrightarrow[H_2 O]{PdCl_2 \, CuCl} CH_3 CHO$
Since on ozonolysis, only alkenes produce aldehydes, '$A$' must be an alkene. To decide the structure of alkene that undergoes ozonolysis, bring the products together in such a way that $O$ atoms are face to face and, replace $O$ by double (=) bond. Thus,

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