ANSWER

REACTION

Reduction or Hydogenation of Alkene double bond takes place to Alkanes single bond in presence of
Adam’s catalyst (PtO2) in Acetic Acid/MeOH medium at 50 psi. Rest all bonds are not affected.

EXPLANATION

Platinum dioxide also known as Adam’s catalyst, is usually represented as platinum(IV) oxide
hydrate, PtO2•H2O. It is a catalyst for hydrogenation and hydrogenolysis in organic synthesis.

The oxide itself is not an active catalyst, but it becomes active after exposure to hydrogen
whereupon it converts to platinum black, which is responsible for reactions.

Adams' catalyst is used for many applications. It has shown to be valuable for hydrogenation,
hydrogenolysis, dehydrogenation, and oxidation reactions. During the reaction, platinum metal
(platinum black) is formed which has been cited to be the active catalyst. Hydrogenation occurs with
syn stereochemistry when used on an alkyne resulting in a cis-alkene. Some of the most important
transformations include the hydrogenation of ketones to alcohols or ethers (the latter product
forming in the presence of alcohols and acids) and the reduction of nitro compounds to amines.
However, reductions of alkenes can be performed with Adam's catalyst in the presence of nitro
groups without reducing the nitro group. When reducing nitro compounds to amines, platinum
catalysts are preferred over palladium catalysts to minimize hydrogenolysis. The catalyst is also used
for the hydrogenolysis of phenyl phosphate esters, a reaction that does not occur with palladium
catalysts. The pH of the solvent significantly affects the reaction course, and reactions of the catalyst
are often enhanced by conducting the reduction in neat acetic acid, or solutions of acetic acid in
other solvents.

MECHANISM

Steps in the hydrogenation of a C=C double bond at a catalyst surface, for example Ni or Pt :
(1) The reactants are adsorbed on the catalyst surface and H2 dissociates.
(2) An H atom bonds to one C atom. The other C atom is still attached to the surface.
(3) A second C atom bonds to an H atom. The molecule leaves the surface.