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.
![### Solvolysis of tert-Butyl Chloride
**Objective:**
Draw a full arrow-pushing mechanism for the solvolysis of tert-butyl chloride as observed in the laboratory.
**Reaction:**
\[ \text{tert-butyl chloride} (\text{C}_4\text{H}_9\text{Cl}) + \text{H}_2\text{O} \rightarrow \text{tert-butyl alcohol} (\text{C}_4\text{H}_9\text{OH}) + \text{HCl} \]
**Chemical Equation:**
\[ \begin{array}{c@{}c@{}c@{}c@{}c@{}c}
& & & | \\
\text{Cl} & - & \text{C} & \left( \begin{matrix}
| \\
\text{C} \\
| \end{matrix} \right) & + & \text{H}_2\text{O} &
\rightarrow \\
& & & | & & & \\
& & | & \\
& \text{OH} & - & \text{C} & \left( \begin{matrix}
| \\
\text{C} \\
| \end{matrix} \right) & + & \text{HCl}
\end{array} \]
**Mechanism:**
1. **Formation of the Carbocation:**
- The chloride ion (Cl⁻) leaves the tert-butyl chloride molecule via heterolytic cleavage.
- This creates a tert-butyl carbocation (a tertiary carbocation) which is highly stabilized due to hyperconjugation and inductive effects from the surrounding alkyl groups.
**Step Illustration:**
\[ (\text{CH}_3)_3\text{C-Cl} \rightarrow (\text{CH}_3)_3\text{C}^+ + \text{Cl}^-\]
2. **Nucleophilic Attack by Water:**
- Water (H₂O), acting as a nucleophile, attacks the positively charged carbon center of the tert-butyl carbocation.
- This attack leads to the formation of an oxonium ion (protonated alcohol).
**Step Illustration:**
\[ (\text{CH}_3)_3\text{C}^+ + \text{H}_2](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F2babee6a-a0c4-4bd8-9fb9-15d7f34728da%2F424011fa-5600-47b1-9718-dd47cb5a1f08%2F5rmm0b7_processed.jpeg&w=3840&q=75)
Step by step
Solved in 3 steps with 2 images
