Comprehension:
Nucleophilic Addition Reactions
Organic compounds containing carbon-oxygen double bond (>C=O ) are called carbonyl group, which is one of the most important functional group in organic chemistry. In aldehydes, the carbonyl group is bonded to a carbon and hydrogen while in ketones, it is bonded to two carbon atoms.The carbonyl compounds in which carbon of carbonyl group is bonded to carbon or hydrogen and oxygen of hydroxyl moiety (-OH) are known as carboxylic acids , while in compounds where carbon is attached to carbon or hydrogen and nitrogen of -NH2 moiety or to halogens are called amides and acyl halides respectively. Aldehydes, ketones, and carboxylic acids are widespread in plants and animal kingdom. They add fragrance and flavour to nature, for example, vanillin ( from vanilla bean), salicylaldehyde ( from meadow sweet ) and cinnamaldehyde ( cinnamon) have pleasant fragrances.
The carbonyl carbon atom is sp2-hybridised and forms three sigma ( σ ) bonds. The fourth valence electron of carbon remains in its p-orbital and forms a π-bond with oxygen by overlap with p-orbital of an oxygen. In addition , the oxygen atom also has two non bonding electron pairs. Thus, the carbonyl carbon and the three atoms attached to it lie in the same plane and the π-electron cloud is above and below this plane. The bond angles are approximately 120° and trigonal coplanar structure.
The carbon-oxygen double bond is polarised due to higher electronegativity of oxygen relative to carbon. Hence, the carbonyl carbon is an electrophilic (Lewis acid), and carbonyl oxygen , a nucleophilic (Lewis base) centre. Carbonyl compounds have substantial dipole moments and are more polar than ethers. Aldehyde and ketone can be prepared by oxidation of alcohols, dehydrogenation of alcohols, and ozonolysis of alkenes etc.
Identify the name reaction and product in the following chemical reaction.
Answer & explanation
Correct answer: option 2
The correct answer is Option (2) → Gattermann-Koch reaction ; Benzaldehyde
Aromatic aldehydes and ketones are prepared by several named reactions, which are recognised from the starting material and the reagent:
Gattermann–Koch reaction: benzene + CO and HCl with anhydrous AlCl3 (or CuCl) gives benzaldehyde.
Etard reaction: toluene + chromyl chloride (\( \ce{CrO2Cl2} \)), then hydrolysis, gives benzaldehyde.
Rosenmund reduction: an acyl chloride + \( \ce{H2} \) over Pd–BaSO4 gives an aldehyde.
Friedel–Crafts acylation: benzene + an acyl chloride with anhydrous \( \ce{AlCl3} \) gives an aromatic ketone.
The reaction shown uses benzene with CO and HCl in the presence of anhydrous \( \ce{AlCl3} \), so it is the Gattermann–Koch reaction, and the product is benzaldehyde.
Why the other options are incorrect
Option (1) Etard Reaction ; Benzaldehyde — Incorrect. The product is right, but the Etard reaction starts from toluene and uses chromyl chloride.
\( \displaystyle \ce{C6H5CH3} \xrightarrow[\text{(ii) }\ce{H3O+}]{\text{(i) }\ce{CrO2Cl2},\ \ce{CS2}} \ce{C6H5CHO} \)
Option (3) Rosenmund reduction ; Benzoic acid — Incorrect. Rosenmund reduction starts from an acyl chloride and gives an aldehyde, not an acid.
\( \displaystyle \ce{C6H5COCl + H2} \xrightarrow{\ce{Pd}-\ce{BaSO4}} \ce{C6H5CHO + HCl} \)
Option (4) Friedel-Crafts acylation reaction; Benzoyl chloride — Incorrect. Acylation uses an acyl chloride as the reagent and gives a ketone; benzoyl chloride is not its product.
\( \displaystyle \ce{C6H6 + CH3COCl} \xrightarrow{\text{anhyd. }\ce{AlCl3}} \ce{C6H5COCH3 + HCl} \)
NCERT (2026-27 edition):
By Gatterman–Koch Reaction
