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Halogenation of phenols is faster in polar solvents in a basic environment due to the dissociation of phenol, with phenoxide ions being more susceptible to electrophilic attack as they are more electron-rich. Chlorination of toluene with chlorine without catalyst requires a polar solvent as well such as acetic acid.
Halogenation of saturated hydrocarbons is a substitution reaction. The reaction typically involves free radical pathways. The regiochemistry of the halogenation of alkanes is largely determined by the relative weakness of the C–H bonds. This trend is reflected by the faster reaction at tertiary and secondary positions.
Note the decrease in ΔG ‡ activation for the polar-solvent reaction conditions. This arises from the fact that polar solvents stabilize the formation of the carbocation intermediate to a greater extent than the non-polar-solvent conditions. This is apparent in the ΔE a, ΔΔG ‡ activation. On the right is an S N 2 reaction coordinate diagram.
A halogen addition reaction is a simple organic reaction where a halogen molecule is added to the carbon–carbon double bond of an alkene functional group. [1] The general chemical formula of the halogen addition reaction is: C=C + X 2 → X−C−C−X (X represents the halogens bromine or chlorine, and in this case, a solvent could be CH 2 ...
In organic chemistry, free-radical halogenation is a type of halogenation. This chemical reaction is typical of alkanes and alkyl-substituted aromatics under application of UV light. The reaction is used for the industrial synthesis of chloroform (CHCl 3), dichloromethane (CH 2 Cl 2), and hexachlorobutadiene. It proceeds by a free-radical chain ...
Reaction scheme of the photobromination of the methyl group of toluene Photobromination with elemental bromine proceeds analogous to photochlorination also via a radical mechanism. In the presence of oxygen, the hydrogen bromide formed is partly oxidised back to bromine, resulting in an increased yield.
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Benzyl bromide is used in organic synthesis for the introduction of the benzyl groups when the less expensive benzyl chloride is insufficiently reactive. [6] [7] Benzylations are often achieved in the presence of catalytic amounts of sodium iodide, which generates the more reactive benzyl iodide in situ. [3]