The scheme represents the reaction of an alkene with hydrogen bromide. The reaction occurs via Markovnikovâ€™s rule. The hydrogen atom of the hydrogen bromide gets substituted to the carbon atom that is least substituted. The reaction proceeds through the formation of a carbocation. The addition of hydrogen chloride and hydrogen iodide proceeds through the same mechanistic pathway.
The major reactions of the unsaturated hydrocarbon molecules are the electrophilic addition reactions and oxidation reactions. The reason for undergoing electrophilic addition is because the unsaturated bond increases the nucleophilicity of the carbon atoms and hence, they undergo electrophilic additions. In rare cases, reduction reactions do occur in alkene molecules. Depending upon the harsh reaction conditions, alkenes lose two hydrogen atoms in the form of hydrogen gas and form alkynes. For such reduction reactions, high temperature and catalyst are required.
The most common electrophilic addition reaction is explained as follows: During the electrophilic addition reactions of the alkene molecule, an electrophile is generated. The nucleophile in this reaction is the carbon center along with an unsaturated bond that binds with the electrophilic atom. The nucleophilic carbon atom binds with the electrophilic atom in such a way that a three-membered transition state is formed. This three-membered transition state is highly strained and shows high reactivity. The nucleophile formed during the homolytic or heterolytic cleavage of the molecule attacks the three-membered transition state from the backside. This leads to the opening of a strained transition state and electrophilic addition reactions. The anti- addition of the other substituent is the last step in the addition reaction of alkenes. For electrophilic addition reactions of halogen acids to alkenes, Markovnikov and anti-Markovnikov rules are followed. As per the Markovnikov rule, the positive part of the halogen acid i.e., hydrogen, binds to that alkyl group that has a higher number of hydrogen atoms, and the negative part which is the halogen atom, binds to the carbon atom which has less number of hydrogen atoms. The reverse of the Markovnikov rule is followed in the case of the anti-Markovnikov rule. The anti-Markovnikov addition of alkenes is followed when the addition reaction takes place in the presence of no light or basically in dark conditions. The other important condition to follow anti-Markovnikov addition is the usage of a peroxide-based reagent, such as hydrogen peroxide, barium peroxide, or sodium peroxide.
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