Reading a scheme

Start with the conditions. A strong base, an acid, a metal, a peroxide: the reagent line narrows the reaction type before you look at a single bond.

Find what changed. Compare starting material and product atom by atom: which bond formed, which left, and whether the carbon count grew.

Substitution vs. elimination vs. addition is a bookkeeping question: same number of σ bonds, fewer, or more.

Mechanism follows structure. A tertiary or benzylic center with a weak nucleophile points to a cation; a primary center with a strong nucleophile does not.

Every example here is a real reaction with a real citation. The yields are the authors’ own.

Enols and enolate formation (fundamentals): All · Keto–enol tautomerization · Silyl enol ethers · Kinetic enolates · Alkene isomerization · Enamines · Enol esters · Thermodynamic enolates · Imine–enamine tautomerization · Lactam–lactim tautomerization

Imine–enamine tautomerization

1 real reaction from the literature, on enamines. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.

Loading examples…

Imine–enamine tautomerization: an enamine gives the tautomer.

Imine–enamine tautomerizationJ. Am. Chem. Soc. 1964, 86, 4283