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Hello Guys, In this Lecture, we are going to discuss a very important topic from Organic reaction Mechanism- SN1 for Jee Mains, Advanced , NEET and AIIMS.
A nucleophilic substitution reaction that occurs by an SN1 mechanism proceeds in two steps. In the first step, the bond between the carbon atom and the leaving group breaks to produce a carbocation and, most commonly, an anionic leaving group. In the second step, the carbocation reacts with the nucleophile to form the substitution product.
The formation of a carbocation is the slow, or rate-determining, step. The subsequent step, formation of a bond between the nucleophile and the carbocation, occurs very rapidly. Because the slow step of the reaction involves only the substrate, the reaction is unimolecular.Because only the substrate is present in the transition state, the rate of the reaction depends only on its concentration, and not on the concentration of the nucleophile.
Figure 7.3 shows an energy diagram tracing the progress of a reaction that occurs by an SN1 mechanism. The rate of the reaction reflects the activation energy required to form the carbocation intermediate. The activation energy required for step 2, addition of the nucleophile to the carbocation, is much smaller, so step 2 is very fast. The rate of step 2 has no effect on the overall rate of the reaction.
The rates of SN1 reactions decrease in the order 3° 2° 1°, which is the reverse of the order observed in SN2 reactions. The relative reactivity of haloalkanes in SN1 reactions corresponds to the relative stability of carbocation intermediates that form during the reaction. We recall from Chapter 4 that the order of stability of carbocations is tertiary secondary primary. A tertiary carbocation forms faster than a less stable secondary carbocation, which in turn forms very much faster than a highly unstable primary carbocation. However, SN1 mechanisms are also favored by resonance-stabilized primary carbocations such as benzyl and allyl.
In contrast to SN2 reactions at stereogenic centers, which occur with inversion of configuration, an SN1 reaction gives a racemic mixture of enantiomers that has no optical rotation. For example, (S)-3-bromo-3-methylhexane reacts with water to give a racemic mixture of 3-methyl-3-hexanols. The reaction occurs via an achiral carbocation intermediate with a plane of symmetry (Figure 7.4). The carbocation intermediate’s plane of symmetry allows the nucleophile to attack equally well from either side. The product is then a racemic mixture of enantiomers. Thus, a chiral substrate loses chirality in a reaction that occurs by an SN1 mechanism.
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