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Hammond's postulate is useful for understanding the relationship between the rate of a reaction and the stability of the products. While the rate of a reaction depends just on the activation energy (often represented in organic chemistry as ΔG ‡ “delta G double dagger”), the final ratios of products in chemical equilibrium depends only ...
Carbocations were also found to be involved in the S N 1 reaction, the E1 reaction, and in rearrangement reactions such as the Whitmore 1,2 shift. The chemical establishment was reluctant to accept the notion of a carbocation and for a long time the Journal of the American Chemical Society refused articles that mentioned them.
The carbocation intermediate formed in the reaction's rate determining step (RDS) is an sp 2 hybridized carbon with trigonal planar molecular geometry. This allows two different ways for the nucleophilic attack, one on either side of the planar molecule.
The reaction product he obtained instead he called paraceton which he believed to be an acetone dimer. In his second publication in 1860 he reacted paraceton with sulfuric acid (the actual pinacol rearrangement). Again Fittig was unable to assign a molecular structure to the reaction product which he assumed to be another isomer or a polymer.
Adding the hydrogen ion to one carbon atom in the alkene creates a positive charge on the other carbon, forming a carbocation intermediate. The more substituted the carbocation, the more stable it is, due to induction and hyperconjugation. The major product of the addition reaction will be the one formed from the more stable intermediate.
A process approaches pure kinetic control at low temperature and short reaction time. For a sufficiently long time scale, every reaction approaches pure thermodynamic control, at least in principle. [11] [12] This time scale becomes shorter as the temperature is raised. In every reaction, the first product formed is that which is most easily ...
If the substrate that is undergoing S N 2 reaction has a chiral centre, then inversion of configuration (stereochemistry and optical activity) may occur; this is called the Walden inversion. For example, 1-bromo-1-fluoroethane can undergo nucleophilic attack to form 1-fluoroethan-1-ol, with the nucleophile being an HO − group. In this case ...
Hyperconjugation can be used to rationalize a variety of chemical phenomena, including the anomeric effect, the gauche effect, the rotational barrier of ethane, the beta-silicon effect, the vibrational frequency of exocyclic carbonyl groups, and the relative stability of substituted carbocations and substituted carbon centred radicals, and the thermodynamic Zaitsev's rule for alkene stability.