Arrange the steps followed during nucleophilic addition on a carbonyl group.
A. \(sp^2\) hybridised carbon of \(>C=O\) group changes to \(sp^3\) hybridised carbon
B. Nucleophile attacks the electrophilic carbon
C. Tetrahedral alkoxide ion is formed
D. Intermediate captures H+ to give neutral product.
Choose the correct answer from the options given below:
Answer & explanation
Correct answer: option 2
The correct answer is Option (2) → B → A → C → D
The carbonyl carbon is electrophilic because the C=O bond is polarised (Cδ+–Oδ−). In nucleophilic addition the new bond to carbon must form before anything else can change at that carbon:
B (first) — the nucleophile attacks the electrophilic carbon; this slow step starts the reaction.
A (second) — the change from sp2 to sp3 happens as the new C–Nu bond forms and the π electrons move onto oxygen; it cannot come before the attack.
C (third) — the result is the tetrahedral alkoxide ion, with the negative charge on oxygen.
D (last) — the alkoxide oxygen takes a proton in the fast second step, giving the neutral product.
\( \displaystyle \ce{R2C=O + Nu^-} \xrightarrow{\text{slow}} \ce{R2C(Nu)-O^-} \xrightarrow[\text{fast}]{\ce{H+}} \ce{R2C(Nu)-OH} \)
Shortcut: the attack of the nucleophile must come first and the protonation last. Only Option (2) starts with B and ends with D.
NCERT (2026-27 edition):
Mechanism of Nucleophilic Addition Reactions – “A nucleophile attacks the electrophilic carbon atom of the polar carbonyl group from a direction approximately perpendicular to the plane of sp2 hybridised orbitals of carbonyl carbon (Fig. 8.2). The hybridisation of carbon changes from sp2 to sp3 in this process, and a tetrahedral alkoxide intermediate is produced. This intermediate captures a proton from the reaction medium to give the electrically neutral product.”
