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.

Oxidative cleavage of alkenes and diols

1 real reaction from the literature, on 1,2-diols. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.

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Oxidative cleavage: di-tert-butyl tartrate (a 1,2-diol) with Pb(OAc)4; benzene (gives 2 equiv of the glyoxylate) gives tert-butyl 2-oxoacetate (the aliphatic aldehyde).

Oxidative cleavageOrg. Synth. Coll. Vol. 4, p. 124