Common organic reaction types (substitution, elimination, addition, oxidation) and their general mechanism pattern. Front: the reaction name or reagent set. Back: what it does and to which functional group.
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- SN2 reaction
- Bimolecular nucleophilic substitution of an alkyl halide by a nucleophile with inversion of stereochemistry in one concerted step
- SN2 substrates (best for)
- Primary alkyl halides and alkyl tosylates; requires strong nucleophile and aprotic solvent
- SN1 reaction
- Unimolecular nucleophilic substitution via a carbocation intermediate in two steps with racemization of stereochemistry
- SN1 substrates (best for)
- Tertiary and benzylic or allylic alkyl halides in polar protic solvents; weak nucleophiles acceptable
- E2 reaction
- Bimolecular elimination from an alkyl halide with base to form an alkene in one concerted step
- E2 major product
- The more substituted alkene (Zaitsev's rule); H and X must be anti-periplanar
- E1 reaction
- Unimolecular elimination via a carbocation intermediate to form an alkene in two steps
- E1 and SN1 reactions
- Both proceed through the same carbocation intermediate and compete with each other
- Hofmann elimination
- Thermal elimination of a quaternary ammonium hydroxide to form the less substituted alkene and a tertiary amine
- Hydrogenation of an alkene
- Addition of H2 across a C=C double bond using a metal catalyst (Pt, Pd, Ni) to form an alkane
- Hydrogenation of an alkyne
- Addition of H2 to a C≡C triple bond; Lindlar catalyst (poisoned Pd) stops at the alkene stage
- Catalytic hydrogenation stereochemistry
- Both hydrogen atoms add from the same face of the double bond (syn addition)
- Hydration of an alkene
- Addition of H and OH across a C=C using dilute H2SO4 to form an alcohol, following Markovnikov's rule
- Markovnikov's rule
- In addition reactions, H adds to the carbon with more H atoms; OH or halogen adds to the more substituted carbon
- Hydrohalogenation of an alkene
- Addition of HX (X = Cl, Br, I) across a C=C to form an alkyl halide, following Markovnikov's rule