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- Allylic_rearrangement abstract "An allylic rearrangement or allylic shift is an organic reaction in which the double bond in an allyl chemical compound shifts to the next carbon atom. It is encountered in nucleophilic substitution.In reaction conditions that favor a SN1 reaction mechanism the intermediate is a carbocation for which several resonance structures are possible. This explains the product distribution (or product spread) after recombination with nucleophile Y. This type of process is called an SN1' substitution. Alternatively, it is possible for nucleophile to attack directly at the allylic position, displacing the leaving group in a single step, in a process referred to as SN2' substitution. This is likely in cases when the allyl compound is unhindered, and a strong nucleophile is used. The products will be similar to those seen with SN1' substitution. Thus reaction of 1-chloro-2-butene with sodium hydroxide gives a mixture of 2-buten-1-ol and 1-buten-3-ol: reaction of 1-chloro-2-butene with sodium hydroxideNevertheless, the product in which the OH group is on the primary atom is minor. In the substitution of 1-chloro-3-methyl-2-butene, the tertiary 2-methyl-3-buten-2-ol is produced in a yield of 85%, while that for the primary 3-methyl-2-buten-1-ol is 15%.In one reaction mechanism the nucleophile attacks not directly at the electrophilic site but in a conjugate addition over the double bond:SN2 accent reaction mechanism".
- Allylic_rearrangement thumbnail AllylicRearrangementReaction.png?width=300.
- Allylic_rearrangement wikiPageID "1836606".
- Allylic_rearrangement wikiPageRevisionID "541193933".
- Allylic_rearrangement hasPhotoCollection Allylic_rearrangement.
- Allylic_rearrangement subject Category:Reaction_mechanisms.
- Allylic_rearrangement subject Category:Rearrangement_reactions.
- Allylic_rearrangement type ChemicalProcess113446390.
- Allylic_rearrangement type ChemicalReaction113447361.
- Allylic_rearrangement type Mechanism113512506.
- Allylic_rearrangement type NaturalProcess113518963.
- Allylic_rearrangement type PhysicalEntity100001930.
- Allylic_rearrangement type Process100029677.
- Allylic_rearrangement type ReactionMechanisms.
- Allylic_rearrangement type RearrangementReactions.
- Allylic_rearrangement comment "An allylic rearrangement or allylic shift is an organic reaction in which the double bond in an allyl chemical compound shifts to the next carbon atom. It is encountered in nucleophilic substitution.In reaction conditions that favor a SN1 reaction mechanism the intermediate is a carbocation for which several resonance structures are possible. This explains the product distribution (or product spread) after recombination with nucleophile Y. This type of process is called an SN1' substitution.".
- Allylic_rearrangement label "Allylic rearrangement".
- Allylic_rearrangement label "Allylomlegging".
- Allylic_rearrangement label "Réarrangement allylique".
- Allylic_rearrangement label "Transposición alílica".
- Allylic_rearrangement sameAs Transposición_alílica.
- Allylic_rearrangement sameAs Réarrangement_allylique.
- Allylic_rearrangement sameAs Trasposizione_allilica.
- Allylic_rearrangement sameAs Allylomlegging.
- Allylic_rearrangement sameAs m.05_v0n.
- Allylic_rearrangement sameAs Q2695010.
- Allylic_rearrangement sameAs Q2695010.
- Allylic_rearrangement sameAs Allylic_rearrangement.
- Allylic_rearrangement wasDerivedFrom Allylic_rearrangement?oldid=541193933.
- Allylic_rearrangement depiction AllylicRearrangementReaction.png.
- Allylic_rearrangement isPrimaryTopicOf Allylic_rearrangement.