Anti-markovnikov Addition

Question

In presence of peroxides, HBr addition to propene gives:

RankGuru · Accepted Answer

1. **Kharasch Effect**: In the presence of organic peroxides ($R-O-O-R$), $HBr$ adds to alkenes via a **free radical mechanism** instead of the standard carbocation pathway.
2. **Radical Generation**: Peroxides initiate the cleavage of $HBr$ to form a Bromine radical ($Br\cdot$).
3. **Addition Step**: The $Br\cdot$ radical adds to the alkene first. It prefers to add to the terminal carbon to leave behind the more stable **secondary radical** ($CH_3-\dot{C}H-CH_2Br$).
4. **Hydrogen Transfer**: This secondary radical then abstracts a hydrogen atom from another $HBr$ molecule.
5. **Regiochemistry**: The result is **Anti-Markovnikov addition**, where the Bromine ends up on the terminal carbon, producing **1-Bromopropane**.
6. **Note**: This effect is highly specific to $HBr$ (not $HCl$ or $HI$).

Anti-markovnikov Addition

Select the correct option:

🔒 Solution Hidden from View

More hydrocarbons Practice Questions

A hydrocarbon with the molecular formula $C_{6} H_{10}$ is being analysed, and the total number of degr...

Among but-1-ene, cis-but-2-ene, trans-but-2-ene, and 2-methylpropene, the most thermodynamically sta...

Bromine adds to cyclohexene to form a dibromide, and the stereochemical relationship between the two...

Propene is subjected to hydroboration with diborane followed by oxidation using alkaline hydrogen pe...

When 2-methylbutane undergoes monochlorination, several constitutional isomers form, and the total n...

Benzene reacts with acetyl chloride in the presence of anhydrous aluminium chloride, and the major a...

A planar cyclic conjugated species is being assessed for aromatic character, and the number of deloc...

Restricted rotation about a carbon-carbon double bond can give rise to geometrical isomers, and the ...

Among ethane, ethene, and ethyne, the relative ease with which a terminal hydrogen is removed as a p...

A colourless organic liquid decolourises cold dilute alkaline potassium permanganate solution rapidl...

Hydrogen bromide is added to propene in the absence of any peroxide, and the major organic product n...

An unknown symmetrical alkene on reductive ozonolysis yields only propanal as the carbonyl product, ...

About This Question

Solution

Anti-markovnikov Addition

Select the correct option:

🔒 Solution Hidden from View

More hydrocarbons Practice Questions

A hydrocarbon with the molecular formula C6​H10​ is being analysed, and the total number of degr...

Among but-1-ene, cis-but-2-ene, trans-but-2-ene, and 2-methylpropene, the most thermodynamically sta...

Bromine adds to cyclohexene to form a dibromide, and the stereochemical relationship between the two...

Propene is subjected to hydroboration with diborane followed by oxidation using alkaline hydrogen pe...

When 2-methylbutane undergoes monochlorination, several constitutional isomers form, and the total n...

Benzene reacts with acetyl chloride in the presence of anhydrous aluminium chloride, and the major a...

A planar cyclic conjugated species is being assessed for aromatic character, and the number of deloc...

Restricted rotation about a carbon-carbon double bond can give rise to geometrical isomers, and the ...

Among ethane, ethene, and ethyne, the relative ease with which a terminal hydrogen is removed as a p...

A colourless organic liquid decolourises cold dilute alkaline potassium permanganate solution rapidl...

Hydrogen bromide is added to propene in the absence of any peroxide, and the major organic product n...

An unknown symmetrical alkene on reductive ozonolysis yields only propanal as the carbonyl product, ...

About This Question

Solution

A hydrocarbon with the molecular formula $C_{6} H_{10}$ is being analysed, and the total number of degr...