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NEET CHEMISTRYAldehydes, Ketones and Carboxylic AcidsMedium

Question

The correct order of reactivity of phenyl magnesium bromide (PhMgBr) with the following compounds will be: I, II, III

A

I > II > III

B

III > II > I

C

II > I > III

D

I > III > II

Step-by-Step Solution

Phenyl magnesium bromide (PhMgBrPhMgBr) is a Grignard reagent. The reaction involves the nucleophilic attack of the phenyl group (PhPh^-) on the electrophilic carbonyl carbon (>C=O>C=O) of the substrate. The reactivity is governed by two main factors described in organic reaction mechanisms:

  1. Steric Hindrance: The presence of bulky alkyl or aryl groups around the carbonyl carbon hinders the approach of the nucleophile. Therefore, less hindered compounds react faster (e.g., Aldehydes > Ketones).
  2. Electronic Effects: Electron-donating groups (like alkyl groups via +I effect or aryl groups via resonance) decrease the magnitude of the positive charge on the carbonyl carbon, reducing its electrophilicity and reactivity.

The order I > II > III implies a sequence where Compound I is the least sterically hindered and most electrophilic (likely an aldehyde like acetaldehyde), Compound II is intermediate (likely a ketone like acetone), and Compound III is the most hindered/least electrophilic (likely a bulky ketone like benzophenone or acetophenone). This trend is consistent with standard nucleophilic addition reactivity.

Exam Context & Concepts Covered

This question aligns with the NEET CHEMISTRY syllabus, specifically targeting concepts from Aldehydes, Ketones and Carboxylic Acids. Mastering this topic is crucial for scoring well in the upcoming medical entrance examinations. Solving conceptually related problems will help you understand the nuances of these concepts and improve your problem-solving speed.

CHEMISTRYAldehydes, Ketones and Carboxylic Acidscorrectreactivityphenylmagnesiumbromide

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