Question

For the following hydrogenation reaction, draw the correct organic product and select the correct IUPAC name for the organic reactant. When drawing hydrogen atoms on a carbon atom, either include all hydrogen atoms or none on that carbon atom, or your structure may be marked incorrect.

Draw the correct products, in either order, for the following oxidative cleavage reaction.

Answer 1

Concepts and reason

Two reactions are given whose product with the correct organic product with the correct IUPAC name of the reactant needs to be written. Also, assign E/Z nomenclature to the given alkene by assigning priorities to the groups attached at the double bond carbon atom.

First reaction is catalytic hydrogenation of alkene and second reaction is oxidation reaction in the presence of potassium permanganate. Thus, form the reduction and the oxidation product following the correct me4chanism.

Fundamentals

• The hydrogenation of alkene, that is, the addition of hydrogen to the alkene on metal surface follows syn addition. In syn addition, the addition of the group occurs from the same side as shown below:

• Potassium permanganate is a strong oxidising reagent and it can cleave ${\rm{\pi }}$ as well as ${\rm{\sigma }}$ bond. Cold ${\rm{KMn}}{{\rm{O}}_{\rm{4}}}$ oxidises the double bond to diols but hot ${\rm{KMn}}{{\rm{O}}_{\rm{4}}}$ can oxidise the terminal double bond to acids or internal double bonds to mixture of ketone and acid. Consider the following example:

• E/Z system of nomenclature: Geometrical isomers can be given name by using E/Z system based on the priority given to the substituents based on the molecular weights.

If the bulky substituents are lie opposite side then the isomer is termed as E and if the substituents are on the same side then it is termed as Z.

Write the name of the given reactant by giving the priority to the group having greater atomic weight as shown below:

Now, write the correct product of the given catalytic hydrogenation reaction as shown below:

Write the product of the oxidation reaction of the given compound as shown below:

Thus, the double bond is oxidised to form the corresponding acid.

Ans: