Trifluoroiodomethane in basic medium
You didn't give a mechanism for your expected product, so I can only speculate as to how you intended to form the final product.

If you thought to use an Sn2 mechanism, I'd say that the reaction is highly improbable as the halide is attached to a trisubstituted carbon, i.e. a carbon with a lot steric hinderance, and therefore, it would be rather difficult for an Sn2 reaction to take place.

If you chose to use an Sn1 mechanism: with the first step, when iodine leaves, you would create a primary carbocation, which is unstable. Additionally, being that fluorine is an electron withdrawing group, the three fluorines would likely serve to further retract electrons from the already electron-poor carbon, and not serve to stabilize the primary carbocation. Therefore, I doubt that this reaction would occur as well.

In the textbook provided mechanism, the oxygen attacks the accesible iodine, which is next to a very psuedopositive carbon. And although this places a  negative charge  on the carbon atom, the electron-withdrawing fluorines serve to help stabilize the carbanion via their inductive properties. In the second step, the carbons rids itself of its negative charge, by taking a hydrogen atom from a nearby hypoiodous acid (pKa 11).

References:
McMurry, J. (2015). Organic chemistry: with biological applications. Stamford, CT: Cengage Learning.