Question
Download Solution PDFIn organic chemistry, which of the following is an empirical rule used to predict the regioselectivity of electrophilic addition reactions of alkanes and alkynes?
Answer (Detailed Solution Below)
Detailed Solution
Download Solution PDFThe correct answer is Markovnikov's rule.
Key Points
- Markovnikov's rule:
- Markovnikov's rule is a principle that predicts the outcome of an addition reaction of an unsymmetrical alkene.
- It states that in the addition of a polar reagent to an unsymmetrical alkene, the electrophile will add to the carbon atom that has the most hydrogen atoms attached to it, while the nucleophile will add to the carbon atom that has the least hydrogen atoms attached to it.
- This is because the more substituted carbocation intermediate is more stable due to the electron-donating effect of the alkyl groups.
- This rule is named after Russian chemist Vladimir Markovnikov who first proposed it in 1869.
Additional Information
| Rule | Description |
|---|---|
| Cornforth's rules |
A set of rules that predict the stereochemistry of certain types of organic reactions. Rule 1: In an electrocyclic reaction, the new sigma bond is formed in such a way as to maximize the overlap of the interacting orbitals. Rule 2: In a cycloaddition reaction, the new sigma bonds are formed in such a way as to minimize the number of four-membered rings formed. |
| Bredt's rule |
A rule that states that a double bond cannot be located at the bridgehead of a bridged bicyclic system if it leads to a strained conformation. This is because the double bond would introduce additional ring strain, making the molecule less stable. |
| Baldwin's rules |
A set of rules that describe the feasibility and stereochemistry of intramolecular reactions. The rules specify the minimum number of atoms in the transition state of a reaction, as well as the angles between the reacting bonds. The rules are as follows: Rule 1: The number of atoms in the transition state of a reaction cannot exceed the number of atoms in the smallest ring that can be drawn around the reacting bonds. Rule 2: The angles between the reacting bonds must correspond to bond angles in stable molecules. Rule 3: The reaction must proceed through a transition state that is no more strained than the reactant or product. |
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