diff --git a/docs/snc4mz.md b/docs/snc4mz.md index 9f6ffce..5302bb2 100644 --- a/docs/snc4mz.md +++ b/docs/snc4mz.md @@ -392,6 +392,59 @@ $$\ce{alkene + H2O ->[6 mol/L H+] alkaneOH}$$ !!! example (Source: Kognity) +### Nucleophilic substitution + +!!! definition + - A **nucleophile** is a species with a lone pair or a negative charge. + +Nucleophilic substitution replaces a group of atoms attached to a C with a nucleophile. Both processes involve the **leaving group** taking both electrons, becoming negative in the process, and forming a carbocation as the other product, which attracts and bonds with the nucleophile. + +Effectively all reactions here involve the formation or stealing of dative covalent bonds. + +Where $\ce{X}$ is a halogen: +$$\ce{R-X_{(l)} + OH-_{(aq)} -> R-OH_{(aq)} + X-_{(aq)}}$$ + +If substituting with hydroxide, it must be **warm** and **aqueous** (dilute). + +Generally: + +| Carbocation type | Substitution type | +| --- | --- | +| Primary | SN2 | +| Secondary | Both/either | +| Tertiary | SN1 | + +#### SN1 + +This **two-step** reaction involves the heterolytic fission of the C-X bond to form a carbocation + halide ion (slow), followed by the nucleophile's lone pairs/negative charge attracting it to the carbocation. + +The "1" refers to the order of the rate-limiting step being a **unimolecular** collision. + + +(Source: Kognity) + +!!! warning + Be sure to draw VSEPR, unlike in the diagrams above. + +#### SN2 + +This **single-step** reaction has the nucleophile forming a bond with the central atom **opposite the leaving group** in a "back-side attack". The oncoming nucleophile repels the other groups, causing them to move away, effectively **reflecting** ("inverting") the remaining groups across the vertical axis. + +The "2" refers to the order of the rate-limiting step being a **bimolecular** collision. + +(Source: Kognity) + +!!! warning + Dashes must be drawn for the transition state for bonds breaking/forming. In this case, drawing the front/back lines for the bottom two atoms may be ignored in favour of regular lines instead to avoid the ambiguity of forming bonds. + +#### Factors affecting substitution type + +**Steric hindrance** is the effect of other parts of a molecule getting in the way to the central atom, preventing a reaction. If there is not enough space for a backside attack, SN2 cannot happen. Therefore, this makes 3° SN2 substitution not viable. + +**Steric stress reduction** is the resistance of groups against being forced together. In a 3° carbocation, pushing the groups together for a backside attack increases steric stress. This encourages SN1 substitution **only for 3°** to maintain a tetrahedral geometry. + +The **positive inductive effect** is the effect that causes more highly substituted carbons to be more stable. Electrons on neighbouring carbon atoms can move closer to the carbon ion, creating an electron-donating effect that slightly balances its charge, increasing its stability and thus window of opportunity for a **SN1** substitution. + ### Alcohols An **alcohol** is an organic compound with a $\ce{-OH}$ (hydroxyl) functional group.