Complete the following sequence of reactions:

Problemas resueltos de alquinos


SOLUTION:
A(C9H12 ) has four unsaturations, three of which are hydrogenable (double and triple bonds). The fourth non-hydrogenatable unsaturation is a cycle.
Hydration with mercuric sulfate and hydrogenation with Lindar's catalyst indicate that A has a triple bond (2 unsaturations), The other two unsaturations are a double bond and a cycle . The last reaction allows us to determine the structure of compound A.

Problemas resueltos de alquinos

the compound breaks with ozone giving the expected products. Now all that remains is to find the molecule that, by reaction with H2 /Lindlar, gives the compound

Problemas resueltos de alquinos

Once the structure of compound A has been determined, we complete the rest of the reactions:

Problemas resueltos de alquinos

 



Problemas resueltos de alquinos

 


Problemas resueltos de alquinos

 

 


Problemas resueltos de alquinos

 


Problemas resueltos de alquinos