1 bromo 3 clorocyclobutane + Metallic sodium = ? ( the medium of reaction is dioxane )?
Ah, this is the Wurtz reaction.
Typically, you would react two alkyl halides to form an alkane that consists of their respective
#"R"-"Br" + "R"'-"Cl" stackrel("Na"(s)" ")(->) "R"-"R"'#
(with loss of#"NaCl"# and then#"NaBr"# )An example of the mechanism with methyl chloride and ethyl bromide would be:
- Since sodium has a radical
#3s# electron, it donates it to the more electronegative halogen (#"Cl"# ), and#"Cl"^(-)# donates one bonding electron, to form#"NaCl"# . The remaining radical electron goes to form an alkyl radical.- The reactive alkyl radical then reacts with another sodium atom to become a nucleophile. Since sodium has a low electronegativity compared to carbon (
#0.93# vs.#2.5# ),#"R"-"Na"# is really more like#"R":^((-))""^((+))"Na"# .- Finally, the nucleophile acts in an
#bb("S"_N2)# backside-attack on the other alkyl halide to form the final product.So the end result is that the
#"R"# and#"R"'# groups of two alkyl halides combine. Don't forget to count your carbons!In the case of your reaction, dioxane is a refluxed solvent, and at the temperature this reaction is performed for 1-bromo-3-chlorocyclobutane, sodium is a liquid.
A bond is made between the two halide centers.
Remember that the more electronegative halogen leaves first, while the better leaving group during the substitution step is the larger halogen (more acidic conjugate acid).
Since the intramolecular reaction occurs faster than the intermolecular reaction, the major product is made through the nucleophilic center attacking within the same molecule.
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1-Bromo-3-chlorocyclobutane reacts with metallic sodium in dioxane to form 1,3-cyclobutadiene.
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The reaction between 1-bromo-3-chlorocyclobutane and metallic sodium in dioxane medium is a type of nucleophilic substitution reaction known as a "Finkelstein reaction." In this reaction, the nucleophilic chlorine atom in 1-bromo-3-chlorocyclobutane is replaced by the more reactive nucleophile, sodium. The general reaction mechanism can be represented as follows:
1-bromo-3-chlorocyclobutane + Sodium → 1-chloro-3-sodiumcyclobutane + Sodium bromide
The specific product formed in this reaction is 1-chloro-3-sodiumcyclobutane, and sodium bromide is produced as a byproduct. This reaction is typically carried out in an inert solvent like dioxane to facilitate the reaction while preventing undesired side reactions.
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When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.
When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.
When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.
When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.
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