The most stable free radical among the following is (1) C6 H5 C H2 (2) CH3-Ċ H-CH3 (3) C6 H5 Ċ H

The most stable free radical among the following is (1) C6...

The most stable free radical among the following is (1) $\mathrm{C}_6 \mathrm{H}_5 \mathrm{C} \mathrm{H}_2$ (2) $\mathrm{CH}_3-\dot{\mathrm{C}} \mathrm{H}-\mathrm{CH}_3$ (3) $\mathrm{C}_6 \mathrm{H}_5 \dot{\mathrm{C}} \mathrm{HCH}_3$ (4) $\mathrm{CH}_3 \dot{\mathrm{C}} \mathrm{H}_2$ (a) $3>1>4>2$ (b) $1>3>2>4$ (c) $3>1>2>4$ (d) $3>2>1>4$

The most stable free radical among the following is
(1) $\mathrm{C}_6 \mathrm{H}_5 \mathrm{C} \mathrm{H}_2$
(2) $\mathrm{CH}_3-\dot{\mathrm{C}} \mathrm{H}-\mathrm{CH}_3$
(3) $\mathrm{C}_6 \mathrm{H}_5 \dot{\mathrm{C}} \mathrm{HCH}_3$
(4) $\mathrm{CH}_3 \dot{\mathrm{C}} \mathrm{H}_2$
(a) $3>1>4>2$
(b) $1>3>2>4$
(c) $3>1>2>4$
(d) $3>2>1>4$

Key Concepts

Free Radical Stability

Free radical stability refers to the relative energy and reactivity of molecules containing an unpaired electron. In general, radicals that can stabilize this electron through delocalization or through other electronic effects are lower in energy and hence more stable.

Resonance Stabilization

Resonance stabilization involves the delocalization of the unpaired electron across multiple atoms or bonds, reducing the electron’s localization at one site. This distribution of electron density over a larger framework, especially in conjugated systems or aromatic rings, lowers the overall energy of the radical and enhances its stability.

Hyperconjugation

Hyperconjugation is the stabilizing interaction that arises from the overlap of the electron density of ?-bonds (typically C–H or C–C bonds) with an adjacent empty or partially filled p-orbital. In radicals, the presence of alkyl substituents can donate electron density through hyperconjugation, leading to increased stability of the radical species.

Benzylic Radical

A benzylic radical is a radical that forms on a carbon atom adjacent to an aromatic ring. These radicals benefit from resonance stabilization as the unpaired electron can be delocalized into the aromatic ring, significantly lowering the radical’s energy and increasing its stability compared to radicals without such delocalization.

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