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
Reactive Intermediates
In chemistry, reactive intermediates are termed as short-lived, highly reactive atoms with high energy. They rapidly transform into stable particles during a chemical reaction. In specific cases, by means of matrix isolation and at low-temperature reactive intermediates can be isolated.
Hydride Shift
A hydride shift is a rearrangement of a hydrogen atom in a carbocation that occurs to make the molecule more stable. In organic chemistry, rearrangement of the carbocation is very easily seen. This rearrangement can be because of the movement of a carbocation to attain stability in the compound. Such structural reorganization movement is called a shift within molecules. After the shifting of carbocation over the different carbon then they form structural isomers of the previous existing molecule.
Vinylic Carbocation
A carbocation where the positive charge is on the alkene carbon is known as the vinyl carbocation or vinyl cation. The empirical formula for vinyl cation is C2H3+. In the vinyl carbocation, the positive charge is on the carbon atom with the double bond therefore it is sp hybridized. It is known to be a part of various reactions, for example, electrophilic addition of alkynes and solvolysis as well. It plays the role of a reactive intermediate in these reactions.
Cycloheptatrienyl Cation
It is an aromatic carbocation having a general formula, [C7 H7]+. It is also known as the aromatic tropylium ion. Its name is derived from the molecule tropine, which is a seven membered carbon atom ring. Cycloheptatriene or tropylidene was first synthesized from tropine.
Stability of Vinyl Carbocation
Carbocations are positively charged carbon atoms. It is also known as a carbonium ion.
![**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.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F8c939cff-bc46-4066-b22a-d4e55e2c89ab%2Fe65dd4d8-8369-4b2f-8588-80cb7d87add7%2F7g2nrcv_processed.jpeg&w=3840&q=75)
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