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The effect of the sigma electron displacement towards the more electronegative atom by which one end becomes positively charged and the other end negatively charged is known as the inductive effect. The - I effect is a permanent effect & generally represented by an arrow on the bond.
Distinguishing between both mechanisms requires consideration of inductive and mesomeric effects that could stabilize or destabilize a potential carbocation in the S N 1 pathway. Usage of hydrohalic acids takes advantage of the fact that these agents are able to protonate the ether oxygen atom and also provide a halide anion as a suitable ...
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.
Due to the electron-withdrawing effect of the carbonyl group, the ketone product is always less reactive than the original molecule, so multiple acylations do not occur. Also, there are no carbocation rearrangements, as the acylium ion is stabilized by a resonance structure in which the positive charge is on the oxygen.
An alkyl group which is situated trans- to the leaving –OH group may migrate to the carbocation center, but cis- alkyl groups migrate at a very low rate. In the absence of trans- alkyl groups, ring contraction may occur as the major product instead, i.e. the ring carbon itself may migrate.
A carbocation is an ion with a positively charged carbon atom. Among the simplest examples are the methenium CH + 3, methanium CH + 5, acylium ions RCO +, and vinyl C ...
The three alkyl groups on the tertiary carbon contribute to a strong inductive effect. This is because each alkyl group will share its electron density with the central carbocation to stabilize it. Additionally, the surrounding sp3 hybridized carbons can stabilize the carbocation through hyperconjugation. [5]
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.