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Some Arrow-Pushing Guidelines (Section 1.14)

Organic Chemistry I Review: Highlights of Key reactions , Mechanisms, and Principles 1 Some Arrow-Pushing Guidelines (Section ) 1. Arrows follow electron movement. 2. Some rules for the appearance of arrows The arrow must begin from the electron source. There are two sources: a. An atom (which must have a lone pair to give) b. A bond pair (an old bond that breaks) An arrow must always point directly to an atom, because when electrons move, they always go to some new atom. 3. Ignore any Spectator Atoms. Any metal atom is always a spectator When you have a metal spectator atom, realize that the non-metal next to it must have negative charge 4.

5. E1 Reactions. 3º > 2º > 1º (Controlled by cation stability) Recognition: A. Neutral, weak nucleophile. No anionic nucleophile/base, and B. 3º or 2º alkyl halide. (Controlled by cation stability). (For 2º alkyl halides, E1 is often accompanied by variable amounts of SN1.) Orientation: The most substituted alkene forms

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