Q53E - Organic Chemistry (Mcmurry)

Question

What product(s) would you expect to obtain from the following

reactions?

(a) 

(b) 

(c) 

(d) 

Step-by-Step Solution

Answer

Answer

Step-by-step Solution Step 1: Catalytic Hydrogenation

Catalytic hydrogenation is treatment with hydrogen in the presence of a catalyst such as nickel, palladium, or platinum. The mechanism begins by bonding hydrogen atoms to metal through pressurized hydrogen gas. The compound then bonds to the metal through hydrogen atoms, completing the reduction process.

Step 2: Product obtained for reaction (a)

                                    Catalytic hydrogenation

Catalytic hydrogenation reduces both the aromatic ketone and the nitro group.

Step 3: Nitration

Nitration is a chemical process for the addition or introduction of a nitro group into an organic compound.

For example conversion of toluene to trinitrotoluene (TNT).

Nitration is notably used for the production of explosives.

Step 4: Product obtained for reaction (b)

In this reaction, nitration is followed by reduction with Fe produces substituted anilines.

Step 5: product obtained for reaction (c) and (d)

(c) In this reaction aqueous KMnO₄, oxidizes alkyl side chains to benzoic acid. 

(d) There is a direct substitution of the methoxy group in the given reaction because it is a more powerful activating group. Rearranged and unarranged side chains are present in the product.