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The Cossee-Arlman mechanism propagates a polymer through alkene coordination followed by insertion into a metal–carbon bond. Repetition extends the metal-bound chain. Regioselectivity controls monomer connectivity; it does not by itself specify tacticity.

The favoured insertion leaves nickel attached to the methyl-substituted alkyne carbon; the aryl group bonds to the SiMe${}_3$-substituted carbon. This is the connectivity leading to the illustrated ring-closed product: the carbon carrying methyl subsequently attacks the ester carbonyl.

The bulky trimethylsilyl substituent is kept away from the crowded phosphine-ligated nickel centre in the insertion arrangement. The alternative orientation would place Ni next to the more demanding SiMe${}_3$ end. regioselectivity can also reflect electronic polarization of a silyl-substituted alkyne and stabilization of the resulting alkenyl complex. The ortho ester helps capture the insertion product by oxygen coordination and subsequent ring closure. Steric discrimination at insertion, reinforced by the accessible intramolecular cyclization, accounts for the observed direction; the product drawing alone is not a quantitative separation of steric and electronic contributions.

Write $R$ for the current growing chain. Propene first binds at the available site of $[\mathrm{C}{\mathrm{p}}_2\mathrm{ZrR}{]}^{+}$, giving a coordinated alkene adjacent to the metal-bound chain. In the Cossee-Arlman mechanism, the chain migrates to the substituted alkene carbon while the terminal carbon forms the new Zr–C bond:The electron-pair arrows for insertion take the old Zr–R bond toward the substituted alkene carbon and the alkene pi bond toward the new Zr–terminal-carbon bond. A four-center arrangement permits both bonds to change in one migratory insertion; Zr remains Zr(IV). The product again has an accessible site, so coordination and insertion can repeat.

Predominant 1,2 insertion leaves a primary Zr–CH${}_2$ chain end and generates head-to-tail polypropylene. It avoids the more crowded alternative secondary Zr–CH(Me) end and unfavorable methyl contacts with the cyclopentadienyl ligands in the insertion geometry. This explains regioselectivity. An unbridged, unsubstituted zirconocene does not by itself establish a fixed tacticity; the schematic alignment of methyl groups in a polymer drawing is not evidence for an isotactic product.

A is 1-propyl-1,2,4-triazole, with propyl on the nitrogen that is adjacent to one N and one C in the triazole ring, rather than on the nitrogen between the two carbon atoms.

DBU removes the ring NH proton, producing a resonance-stabilized triazolide anion. Nitrogen attacks the primary bromide carbon by an SN2 reaction, displacing bromide and giving the N-propyl product. Alkylation at the equivalent tautomer-related N1/N2 positions gives the same constitutional product, while N4 alkylation would give a different isomer. Charge distribution in the triazolide and the accessibility of its nitrogen lone pairs favor the N1 product under the stated conditions. This is kinetic regioselectivity, not an assertion that the unalkylated tautomer has a permanently localized negative charge.

Preferential formation of one product or reaction at one site. chemoselectivity, regioselectivity and stereoselectivity describe different comparisons.

Tacticity describes the stereochemical ordering of configurational units along a polymer chain. It is distinct from the head-to-tail or head-to-head connectivity described by regioselectivity.