Question

1-What are the bases that can deprotonate a hydroxyl group OH? 2-what is the first mechanistic step in the reaction between Ethoxide ion and 4-chloro-1-butanol?

Answer 1

1. Depends on a a substance. For example, in carboxylic acids it can be easely deprotonatet by hydroxyl-anione. In the enols there had to be used a stronger base, such as LDA. In water HOH one protone can be removed by adding metal sodium.
2. The first step is deprotonation of OH group of the 4-chloro-1-butanol, and protonation of ethoxie ion formig ethanol.