Why there isn't any unimolecular addition reaction?

In summary, the conversation discusses the differences between unimolecular and bimolecular reactions in organic chemistry. Specifically, the focus is on the mechanism of addition reactions in which a double bond is converted into a single bond. While in unimolecular reactions, the bond automatically breaks and a nucleophile attacks the resulting carbocation, in bimolecular reactions two species must come together to form the new bond. This results in a different reaction rate equation, with the unimolecular reaction being proportional to the concentration of one species only, while the bimolecular reaction is proportional to the concentration of both species involved. The conversation also mentions the stability of molecules with charge separation and how this affects the reaction mechanism.
  • #1
Tahmeed
81
4
In my textbook, i have read about unimolecular elimination and nucleophilic unimolecular substitution reaction of organic compounds. In those reactions, firstly one bond breaks automatically then as soon as a carbocation forms then a nucleophile attacks the carbocation to complete the reaction.

Now, my question is, why the same doesn't happen in case of addition reaction of molecules having double bond? one bond breaking may cause a charge separation and then nucleophile/electrophile can attack the positive or negative charged side? I know molecules with charge separation aren't supposed to be much stable. But even in the case of a carbocation the same happens.

I have googled for unimolecular addition reaction but all the results were about unimolecular substitution/elimination.
 
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  • #2
"Unimolecular" and "bimolecular" refer to the kinetics of the reaction. In other words, in a unimolecular elimination/substitution, the reaction rate looks like:
$$\frac{d[A]}{dt} \propto k[A]$$
whereas a bimolecular reaction rate looks like:
$$\frac{d[A]}{dt} \propto k[A][ B] $$
How would you get a reaction rate that looks unimolecular for an electrophilic alkene addition reaction where two species have to come together?
 

1. Why do unimolecular addition reactions not occur?

Unimolecular addition reactions involve the addition of a molecule to a single reactant molecule, resulting in the formation of a new product. However, this type of reaction is typically not observed in nature or in laboratory settings. This is because unimolecular addition reactions are highly unfavorable due to the high energy requirements needed to overcome the activation energy barrier.

2. What is the difference between unimolecular and bimolecular reactions?

Unimolecular reactions involve a single molecule as the reactant, while bimolecular reactions involve two molecules coming together to form a product. In unimolecular reactions, the rate of reaction is solely dependent on the concentration of the reactant molecule, while in bimolecular reactions, the rate is dependent on the concentration of both reactant molecules.

3. Can unimolecular addition reactions be catalyzed?

In theory, unimolecular addition reactions can be catalyzed, but in practice, it is very difficult to find a catalyst that can overcome the high activation energy barrier and make these reactions favorable. Additionally, catalyzing a unimolecular reaction would require the catalyst to interact with the single reactant molecule, which is not always possible.

4. Are there any exceptions to the rule that unimolecular addition reactions do not occur?

There are a few rare exceptions to this rule, but they are typically limited to specific cases where the reactant molecule is highly unstable or reactive. In these cases, the reactant molecule may undergo a unimolecular addition reaction to form a more stable product.

5. How do unimolecular reactions compare to other types of reactions?

Unimolecular reactions are typically slower than bimolecular reactions due to the higher energy requirements needed to overcome the activation energy barrier. They also tend to be more unpredictable and are less commonly observed in nature. However, unimolecular reactions can play important roles in some chemical processes and are still studied by scientists to gain a better understanding of reaction mechanisms.

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