Acidity of Organic Compounds

"Is CH3CH2OH deprotonated when pH>7, i.e. alkaline?"
"Does ethanol neutralise aqueous sodium hydroxide?"

The answers are: NO!

Acidity decreases in the order: carboxylic acid > phenol > water (it's not acidic!) > alcohol.


"What is the product formed when CH3CHBrCH2CH2COOH is heated with NaOH dissolved in ethanol?"

The product is CH3CH=CHCH2COO-Na+. To get the carboxylic acid, you need to add H2SO4(aq).

Ethanolic NaOH favours elimination while NaOH(aq) favours nucleophilic substitution. That's why ethanolic NaOH is used in the elimination of HBr to form an alkene.

Do note that ethanolic NaOH still contains some water. Elimination of HBr requires OH- ions. In pure ethanol, NaOH does not ionise. Hence, the OH- ions will neutralise the acidic -COOH group.


"Will there be an acid-base reaction between NaOH and HCl in CCl4?"

NO. For NaOH to neutralise HCl, there must be H+ and OH- ions. However, NaOH and HCl do not ionise in CCl4.

NOTE: NaOH is insoluble in CCl4. Thus, the question is actually invalid.