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DEHALOGENATION

Dehalogenation can be defined as a process of removal of halogen atoms from a molecule thus resulting in the formation of a compound with different functional group.

REACTIONS
These are some reactions which undergo dehalogenation reaction in the process of formation of the final product.
1. 2. 3. 4. 5. Wurtz reaction RaschigHooker process Dows process Ammonolysis of substitutued aromatic chloro compounds Nucleophilic Substitution Reactions of Alkyl Halides.

WURTZ REACTION
1. Has its limited importance to the fact that it brings about the union of two alkyl groups and thus yielding an alkane of higher carbon number than the reactant 2. It is suited only for the synthesis for symmetrical alkane R-R.

2 R-X + 2 Na

R-R + 2Na-X

3. For unsymmetrical alkanes the reaction is as follows


3R-X+3R-X +6Na R-R +R-R+R-R+6Na-X

RASCHIGHOOKER PROCESS
1. The RaschigHooker process is a chemical process for the production of phenol starting from Chlorobenzene. 2. In this process phenol is obtained by heating chlorobenzene with steam at 698K using Ca3(PO4)2 or SiO2. 3. It can also be synthesized by using Cu as a catalyst at 673K under pressure. 4. The main steps in this process are the production of chlorobenzene from benzene, hydrochloric acid and oxygen, and followed by the subsequent hydrolysis of chlorobenzene to phenol.

DOWS PROCESS
1. Dow's Process may also refer to the hydrolysis of chlorobenzene in the preparation of phenol. 2. Benzene can be easily converted to chlorobenzene by electrophilic aromatic substitution. O 3. In this process chlorobenzene is heated at 350 C, under high pressure with aq. NaOH, the reaction produces sodium phenoxide, which on acidification yields phenol.

REACTION

Chlorobenzene

Sodium Phenoxide

Phenol

Ammonolysis of aromatic chloro substituted compounds


In this case we do not require any catalyst as the ring is highly deactivated due to the presence of the Nitro group. In this case we make use of 16 moles of NH3 per mole of PNCB

NUCLEOPHILIC SUBSTITUTION REACTION OF ALKYL HALIDES.


1. In this type of reaction a nucleophile, a species with an unshared electron pair, reacts with an alkyl halide thus replacing the halogen substituent. 2. This reaction is initiated by a nucleophile, thus it is called as nucleophilic substitution reaction.

SN1 REACTION
1. The SN1 reaction is a substitution reaction in organic chemistry. 2. "SN" stands for nucleophilic substitution and the "1" represents the fact that the rate-determining step is unimolecular. 3. The reaction of tertiary butyl chloride with sodium hydroxide in a mixture of acetone and water forms a tertiary butyl alcohol is an example of SN1 reaction.

REACTION

t-butyl chloride

Rate [(CH3)-CCl] Rate=K [(CH3)-CCl]

t-butyl alcohol

MECHANISM

SN1 ENERGY DIAGRAM

Rate-determining step is formation of carbocation


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CHARACTERISTICS
1. The rate of reaction is independent of the concentration of the nucleophile 2. Two transition state occur in the course of the reaction 3. Product obtained is a racemic mixture i.e. 50% retention and 50% inversion of configuration. 4. Tertiary alkyl halide are more favoured for the reaction as compared to secondary and primary alkyl halides.

SN2 Reaction
"SN" stands for nucleophilic substitution and the 2" represents the fact that the rate-determining step is bimolecular. The main characteristic of this reaction is that the nucleophile attacks carbon atom containing the leaving group from the back side i.e from the opposite side of the leaving group. In SN2 reaction there is a simultaneous formation of the C-O bond and breaking of the C-N bond. Follows second order (bimolecular) kinetics. That is, rate=k[substrate][nucleophile]

Mechanism

SN2 Energy Diagram

Auwers Synthesis
This is a reaction that involves a step where addition Halogenation is done. This reaction end products are flavonol from a coumarone. The first step in this procedure is an acid catalyzed aldol condensation between benzaldehyde and a 3-oxypentanone to an ohydroxychalcone. Bromination of the alkene group gives a dibromoadduct which rearranges to the flavonol by reaction with potassium hydroxide.

Mechanism

Reaction Alkenes are readily converted by chlorine & bromine into saturated compounds that contain two halogen atoms attached to adjacent carbons.

MECHANISM

Reagents & their Reaction

Halohydrin Formation Addition of chlorine or bromine in the presence of water can yield compounds containing halogen and hydroxyl on adjacent carbon atom.

1. Is made to react with steam at high temperature and pressure thus yielding a phenol. 2. The main steps in this process are the production of chlorobenzene from benzene, hydrochloric acid and oxygen, and followed by the subsequent hydrolysis of chlorobenzene to phenol