Allylic Carbon vs. Vinylic Carbon — What's the Difference?
Edited by Tayyaba Rehman — By Fiza Rafique — Published on December 2, 2023
Allylic Carbon is adjacent to a carbon-carbon double bond, while Vinylic Carbon is directly involved in the double bond itself.
Difference Between Allylic Carbon and Vinylic Carbon
Table of Contents
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Key Differences
In the context of organic chemistry, understanding the distinction between Allylic Carbon and Vinylic Carbon is fundamental. An Allylic Carbon refers to any carbon atom positioned immediately next to a carbon-carbon double bond. This positioning often imparts certain reactive properties to the allylic position.
On the contrary, a Vinylic Carbon is a carbon atom that is directly participating in the double bond, essentially being one of the two carbon atoms forming the double bond. Due to its involvement in the double bond, the Vinylic Carbon is typically less reactive in certain chemical reactions compared to the Allylic Carbon.
The reactivity of the Allylic Carbon is attributed to the potential for resonance stabilization following certain chemical transformations, a property the Vinylic Carbon doesn't possess.
To summarize, while both Allylic Carbon and Vinylic Carbon are related to carbon-carbon double bonds, their positions relative to the double bond and their resulting reactivities vary significantly.
Comparison Chart
Position relative to C=C bond
Adjacent to the double bond
Directly involved in the double bond
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Reactivity
Generally more reactive due to potential for resonance stabilization
Less reactive due to involvement in the double bond
Examples
CH2=CH-CH2- in propene
CH2=CH- in ethene
Hydrogen substitution
Allylic hydrogens can be abstracted in certain reactions
Vinylic hydrogens are less prone to chemical reactions
Common reactions
Often involved in allylic bromination or oxidation
Resistant to many reactions due to double bond involvement
Compare with Definitions
Allylic Carbon
Not involved in the double bond but influenced by its presence.
Even though the Allylic Carbon isn't part of the double bond, it's greatly impacted by it.
Vinylic Carbon
Integral part of the structure of unsaturated hydrocarbons with double bonds.
The properties of alkenes are largely influenced by the nature of the Vinylic Carbon.
Allylic Carbon
Carbon adjacent to the double bond and often more reactive due to resonance stabilization.
Allylic positions are reactive sites in many organic transformations.
Vinylic Carbon
Carbon directly participating in a carbon-carbon double bond.
In ethene, both carbons are Vinylic Carbons.
Allylic Carbon
A carbon atom positioned immediately next to a carbon-carbon double bond.
The last carbon in propene is an example of an Allylic Carbon.
Vinylic Carbon
A carbon that doesn't have the same resonance stabilization as an allylic position.
Vinylic Carbons lack the dynamic reactivity seen in Allylic Carbons.
Allylic Carbon
Carbon that, when transformed, can be stabilized by the neighboring double bond.
Allylic bromination specifically targets the Allylic Carbon due to its unique reactivity.
Vinylic Carbon
Carbon that is less reactive in many reactions due to its involvement in the double bond.
The reactivity of Vinylic Carbons is restricted by their bond commitments.
Allylic Carbon
Carbon that can exhibit unique chemical behaviors due to its proximity to the double bond.
The position of the Allylic Carbon in a molecule can determine its reactivity and fate in a chemical reaction.
Vinylic Carbon
One of the two carbons forming the double bond in alkenes.
Vinylic Carbons are integral to the structure of alkenes.
Common Curiosities
Where can you find a Vinylic Carbon?
A Vinylic Carbon is directly involved in a carbon-carbon double bond.
What defines an Allylic Carbon?
An Allylic Carbon is the carbon immediately next to a carbon-carbon double bond.
How does the reactivity of Vinylic Carbon compare to Allylic Carbon?
Vinylic Carbons are generally less reactive than Allylic Carbons due to their involvement in the double bond.
Why are Allylic Carbons more reactive in certain reactions?
Allylic Carbons can achieve resonance stabilization, making them more reactive in some contexts.
Can both Vinylic and Allylic Carbons be found in the same molecule?
Yes, in molecules with double bonds, Vinylic Carbons form the bond, and Allylic Carbons are adjacent to it.
Is resonance a feature of Vinylic Carbons?
No, resonance is a feature attributed to Allylic Carbons due to their position next to the double bond.
How can you identify an Allylic Carbon in a molecule?
Look for carbons adjacent to, but not part of, a carbon-carbon double bond.
Which carbon is more likely to undergo bromination, Allylic or Vinylic?
Allylic Carbons are more prone to bromination due to their unique reactivity.
Are Vinylic Carbons susceptible to the same reactions as Allylic Carbons?
No, Vinylic Carbons are often less reactive due to their involvement in the double bond.
Are Allylic Carbons directly involved in the double bond?
No, Allylic Carbons are adjacent to, but not part of, the double bond.
Which type of carbon, Allylic or Vinylic, plays a more crucial role in alkene structure?
Vinylic Carbon, as it's directly involved in forming the double bond in alkenes.
Can an alkene have multiple Allylic Carbons?
Yes, larger alkenes can have multiple carbons adjacent to the double bond, all considered Allylic.
What's the significance of the term "vinylic" in organic chemistry?
It refers to the carbon atoms directly involved in double bonds, crucial for understanding alkene reactivity.
Can a carbon atom be both Allylic and Vinylic?
No, a carbon is either involved in the double bond (Vinylic) or adjacent to it (Allylic), but not both.
Are there any specific reactions exclusive to Vinylic Carbons?
Vinylic Carbons, due to their position, often resist reactions that Allylic Carbons can undergo.
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Fiza RafiqueFiza Rafique is a skilled content writer at AskDifference.com, where she meticulously refines and enhances written pieces. Drawing from her vast editorial expertise, Fiza ensures clarity, accuracy, and precision in every article. Passionate about language, she continually seeks to elevate the quality of content for readers worldwide.
Edited by
Tayyaba RehmanTayyaba Rehman is a distinguished writer, currently serving as a primary contributor to askdifference.com. As a researcher in semantics and etymology, Tayyaba's passion for the complexity of languages and their distinctions has found a perfect home on the platform. Tayyaba delves into the intricacies of language, distinguishing between commonly confused words and phrases, thereby providing clarity for readers worldwide.
