Read the following passage given below and answer the question. Andehydes and ketones undergo nucleophilic addition reactions. A nucleophile attacks the electrophilic carbon atom of polar carbonyl group from perpendicular to plane of \(sp^2\) hybridized orbitals of carbonyl carbon. The hybridization of carbon changes from \(sp^2\) \(sp^3\) and a tetrahedral alkoxide intermediate is formed. This captures \(H^+\) to give neutral product. In carboxylic acids, carbonyl carbon is less electrophilic than carbonyl carbon carbon of aldehydes and ketones. |
The correct order of reactivity for addition reaction of following carbonyl compounds with \(C_2H_5MgI\) is (I) Methanal (II) Propan-2-one (III) Ethanal (IV) 2,2,4,4-Tetramethylpentan-3-one Choose the correct answer from the option given below: |
I > III > II > IV IV > III > II > I I > II > IV > III III > II > I > IV |
I > III > II > IV |
The correct answer is option 1. I > III > II > IV. The reactivity of carbonyl compounds towards nucleophilic addition with C₂H₅MgI depends on:
(I) Methanal (HCHO): Methanal has no alkyl group attached to the carbonyl carbon. Hence, there is no +I effect and no steric hindrance. The carbonyl carbon is highly electrophilic. ∴ Most reactive. (III) Ethanal (CH₃CHO): Ethanal has one alkyl group which shows +I effect, reducing electrophilicity slightly compared to methanal. However, steric hindrance is still low. ∴ Less reactive than methanal but more reactive than ketones. (II) Propan-2-one (CH₃COCH₃): It has two alkyl groups, increasing +I effect and steric hindrance, which decreases electrophilicity of the carbonyl carbon. ∴ Less reactive than aldehydes. (IV) 2,2,4,4-Tetramethylpentan-3-one: This ketone is highly bulky due to four methyl groups near the carbonyl carbon. This creates very high steric hindrance, making nucleophilic attack difficult. ∴ Least reactive. Final order of reactivity: Methanal > Ethanal > Propan-2-one > 2,2,4,4-Tetramethylpentan-3-one Hence, I > III > II > IV |