Rank the following radicals in decreasing order of stability. Classify each as primary, second- ary, or tertiary. (a) The isopentyl radical, (CH3)2CHCH₂ - CH₂ (d) (b) The 3-methyl-2-butyl (c) The 2-methyl-2-butyl radical, CH3-CH-CH(CH3)2 radical, CH3-C(CH3)CH₂CH3

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Chapter1: Chemical Foundations
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**Problem 4-30**

Rank the following radicals in decreasing order of stability. Classify each as primary, secondary, or tertiary.

(a) The isopentyl radical, \((CH_3)_2CHCH_2 \cdot CH_2\)

(b) The 3-methyl-2-butyl radical, \(CH_3 \cdot CHCH(CH_3)_2\)

(c) The 2-methyl-2-butyl radical, \(CH_3 \cdot C(CH_3)CH_2CH_3\)

(d) Diagram: A hexagonal carbon ring with a dot indicating a radical on one of the carbons.

### Explanation of Diagram:

The diagram represents a cyclohexyl radical. This is shown as a hexagon (cyclohexane) with a single dot on one of the vertices, indicating the presence of an unpaired electron, typical of a radical species.

### Discussion:

In evaluating the stability of the radicals:

1. **Primary Radical**: The radical is on a carbon bonded to only one other carbon.
2. **Secondary Radical**: The radical is on a carbon bonded to two other carbons.
3. **Tertiary Radical**: The radical is on a carbon bonded to three other carbons.

Tertiary radicals tend to be more stable than secondary radicals, which are more stable than primary radicals due to hyperconjugation and inductive effects from neighboring carbon atoms. The diagram in (d) suggests a stabilized radical, possibly due to resonance within the cyclohexyl structure.
Transcribed Image Text:**Problem 4-30** Rank the following radicals in decreasing order of stability. Classify each as primary, secondary, or tertiary. (a) The isopentyl radical, \((CH_3)_2CHCH_2 \cdot CH_2\) (b) The 3-methyl-2-butyl radical, \(CH_3 \cdot CHCH(CH_3)_2\) (c) The 2-methyl-2-butyl radical, \(CH_3 \cdot C(CH_3)CH_2CH_3\) (d) Diagram: A hexagonal carbon ring with a dot indicating a radical on one of the carbons. ### Explanation of Diagram: The diagram represents a cyclohexyl radical. This is shown as a hexagon (cyclohexane) with a single dot on one of the vertices, indicating the presence of an unpaired electron, typical of a radical species. ### Discussion: In evaluating the stability of the radicals: 1. **Primary Radical**: The radical is on a carbon bonded to only one other carbon. 2. **Secondary Radical**: The radical is on a carbon bonded to two other carbons. 3. **Tertiary Radical**: The radical is on a carbon bonded to three other carbons. Tertiary radicals tend to be more stable than secondary radicals, which are more stable than primary radicals due to hyperconjugation and inductive effects from neighboring carbon atoms. The diagram in (d) suggests a stabilized radical, possibly due to resonance within the cyclohexyl structure.
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