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