Acids and Bases - Organic Chemistry Concepts: An EFL Approach - page 92

Table 6.3 Selected Functional Group Basicities
Compound Class Substrate Conjugate Acid pK a

Carbonyl −7

Phenol −6.4

Ether −3.5

Alcohol −2.4

Water −1.7

Ammonia 9.2

Amines 10.6

6.5.1 Basicity and Nucleophiles
In Chapter 5, we introduced the general idea of a nucleophile. A study of ionic
and lone-pair nucleophiles shows they are mostly the same species as the bases
which we discussed earlier. In many cases, the terms nucleophile and base
seem to be the same. In other words, nucleophiles act as bases and bases act as
nucleophiles.

However, because of various other factors, it is not always true that a strong base
is a good nucleophile. In this topic, we have mostly used the word base when
the reaction takes place with a proton.