Organic Chemistry: Concepts and Applications - Headley Allan D. 2020
Nucleophilic Substitution Reactions at sp3 Carbons
15.4 The Nucleophile
A nucleophile is defined as a species that has at least one unshared pair of electrons, which you will recall from Chapter 7 on acid and bases, is the same definition as a Lewis base. Nu: or Nu:− is the abbreviation used for a nucleophile, which means a nucleus loving species, remember that a nucleus is positive owing to the presence of protons. Nucleophiles can be neutral or can have a negative formal charge, such as the hydroxide ion, which has a formal charge of −1. Other examples of nucleophiles include H2O, R3N:, I−, CN:−, and H2S. For nucleophiles, typically there is only one atom, which is the nucleophilic atom and that is the atom with the unshared pair of electrons, examples are shown below.
Problem 15.3
Which of the following molecules are electrophiles and which are nucleophiles? For each electrophile identified, indicate the electrophilic atom and for the nucleophile, identify the atom with the unshared pair of electrons.
