w-Fluorooleic acid can be isolated from a shrub, Dechapetalum toxicarium, that grows in Africa. The compound is highly toxic to warm-blooded animals; it has found use as an arrow poison in tribal warfare, in poisoning enemy water supplies, and by witch doctors "for terrorizing the native population." Powdered fruit of the plant has been used as a rat poison; hence v-fluorooleic acid has the common name "ratsbane." A synthesis of v-fluorooleic acid is outlined here. Give structures for compounds F-I:

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(1) NaNH2 1-Bromo-8-fluorooctane + sodium acetylide-→ F (C10H17F) (2) I(CH20I (1) KOH (2) H3O NaCN H2 OH o-Fluorooleic acid (46% yield, overall)