Home >
Community >
Is alkyl halide more reactive than vinyl halide towards the nucleophilic substitution reaction?
Upvote
13
Downvote
+ Chemical reactions
+ Chemistry
+ Organic chemistry
Posted by
Kevin Smyth
Is alkyl halide more reactive than vinyl halide towards the nucleophilic substitution reaction?
Vinylic carbon is sp2 hybridized. Direct nucleophilic approach is unfavourable because of electronic repulsion between more electron rich pielectrons and nucleophile.
In SN1 case, a cation is generated in sp2 carbon centre and resides over the sp2 orbital, which is energetically not favourable. So SN1 or SN2 are not favourable.
Allylic systems do show SN1 and SN2 very well. There is no such restriction. Again the show SN1prime and SN2prime also.
Vinylic carbon is sp2 hybridized. Direct nucleophilic approach is unfavourable because of electronic repulsion between more electron rich pielectrons and nucleophile.
In SN1 case, a cation is generated in sp2 carbon centre and resides over the sp2 orbital, which is energetically not favourable. So SN1 or SN2 are not favourable.
Allylic systems do show SN1 and SN2 very well. There is no such restriction. Again the show SN1prime and SN2prime also.
Halogen containing organic compounds are relatively rare in terrestrial plants and animals. The thyroid hormones T3 and T4are exceptions; as is fluoroacetate, the toxic agent in the South African shrub Dichapetalum cymosum, known as "gifblaar". However, the halogen rich environment of the ocean has produced many interesting natural products incorporating large amounts of halogen. Some examples are shown below. The ocean is the largest known source for atmospheric methyl bromide and methyl iodide. Furthermore, the ocean is also estimated to supply 10-20% of atmospheric methyl chloride, with other significant contributions coming from biomass burning, salt marshes and wood-rotting fungi. Many subsequent chemical and biological processes produce poly-halogenated methanes.
Halogen containing organic compounds are relatively rare in terrestrial plants and animals. The thyroid hormones T3 and T4are exceptions; as is fluoroacetate, the toxic agent in the South African shrub Dichapetalum cymosum, known as "gifblaar". However, the halogen rich environment of the ocean has produced many interesting natural products incorporating large amounts of halogen. Some examples are shown below. The ocean is the largest known source for atmospheric methyl bromide and methyl iodide. Furthermore, the ocean is also estimated to supply 10-20% of atmospheric methyl chloride, with other significant contributions coming from biomass burning, salt marshes and wood-rotting fungi. Many subsequent chemical and biological processes produce poly-halogenated methanes.
Vinylic carbon is sp2 hybridized. Direct nucleophilic approach is unfavourable because of electronic repulsion between more electron rich pi electrons and nucleophile.
In SN1 case, a cation is generated in sp2 carbon centre and resides over the sp2 orbital, which is energetically not favourable. So SN1 or SN2 are not favourable.
Allylic systems do show SN1 and SN2 very well. There is no such restriction. Again the show SN1 prime and SN2 prime also.
Vinylic carbon is sp2 hybridized. Direct nucleophilic approach is unfavourable because of electronic repulsion between more electron rich pi electrons and nucleophile.
In SN1 case, a cation is generated in sp2 carbon centre and resides over the sp2 orbital, which is energetically not favourable. So SN1 or SN2 are not favourable.
Allylic systems do show SN1 and SN2 very well. There is no such restriction. Again the show SN1 prime and SN2 prime also.
More
VOTE
Alkyl Halide Occurrence
Halogen containing organic compounds are relatively rare in terrestrial plants and animals. The thyroid hormones T3 and T4are exceptions; as is fluoroacetate, the toxic agent in the South African shrub Dichapetalum cymosum, known as "gifblaar". However, the halogen rich environment of the ocean has produced many interesting natural products incorporating large amounts of halogen. Some examples are shown below.
The ocean is the largest known source for atmospheric methyl bromide and methyl iodide. Furthermore, the ocean is also estimated to supply 10-20% of atmospheric methyl chloride, with other significant contributions coming from biomass burning, salt marshes and wood-rotting fungi. Many subsequent chemical and biological processes produce poly-halogenated methanes.
Alkyl Halide Occurrence
Halogen containing organic compounds are relatively rare in terrestrial plants and animals. The thyroid hormones T3 and T4are exceptions; as is fluoroacetate, the toxic agent in the South African shrub Dichapetalum cymosum, known as "gifblaar". However, the halogen rich environment of the ocean has produced many interesting natural products incorporating large amounts of halogen. Some examples are shown below.
The ocean is the largest known source for atmospheric methyl bromide and methyl iodide. Furthermore, the ocean is also estimated to supply 10-20% of atmospheric methyl chloride, with other significant contributions coming from biomass burning, salt marshes and wood-rotting fungi. Many subsequent chemical and biological processes produce poly-halogenated methanes.
More
VOTE