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Questions and Answers
Explain the role of stability in carbocation intermediates.
Stability of a carbocation has a direct effect on the reaction as it is a reactive intermediate in the electrophilic addition mechanism.
What factors determine the stability of a carbocation?
The stability of a carbocation depends on inductive effect, resonance effect, and hyperconjugation.
Define the positive inductive effect (+I) in carbocations.
Positive inductive effect occurs when an atom or group donates or shares a pair of electrons, acquiring a partial positive charge.
Explain the negative inductive effect (-I) in carbocations.
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How does an electron withdrawing group affect the stability of a carbocation?
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What is the effect of an electron donating group on the stability of a carbocation?
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What is the role of hyperconjugation in determining the stability of a carbocation?
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How many valence electrons does a carbon atom in a carbocation typically have?
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In terms of stability, how do methyl, primary, secondary, and tertiary carbocations compare?
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What are the three sigma covalent bonds typically formed by a carbon atom in a carbocation?
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Study Notes
Carbocation Structure
- The carbon atom in a carbocation is electron deficient, having only six valence electrons used to form three sigma covalent bonds with the substituents.
- The carbon atom has an unoccupied p orbital.
Stability of Carbocation Intermediates
- The stability of a carbocation has a direct effect on the reaction, as it is a reactive intermediate of the electrophilic addition mechanism.
- The stability of a carbocation depends on three factors: inductive effect, resonance effect, and hyperconjugation.
Inductive Effect
- Positive inductive effect (+I): occurs when an atom or group of atoms donates or shares a pair of electrons, acquiring a partial positive charge.
- Electron donating or releasing groups show a +I effect.
- Negative inductive effect (-I): occurs when an atom or group of atoms withdraws or attracts shared pair of electrons, acquiring a partial negative charge.
- Electron withdrawing or accepting groups show a -I effect.
- Electron withdrawing groups (EWG) destabilize a carbocation, while electron donating groups stabilize a carbocation.
Hyperconjugation and Stability of Carbocations
- The relative stability of methyl, primary, secondary, and tertiary carbocations can be explained in terms of hyperconjugation and inductive effects.
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Description
Test your knowledge on carbocation structure and stability by arranging a series of carbocations in order of increasing or decreasing stability. Understand the relative stability of methyl, primary, secondary, and tertiary carbocations in terms of hyperconjugation and inductive effects.
