Solubility
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Solubility. Like dissolves like. Organic compounds are not expected to be soluble in water. Rule of Thumb: C/O ratio. However,. If the organic compound can be ionized. It is more likely to be water-soluble. since ionic compounds are polar, and thus water-soluble.

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Solubility

Solubility

Like dissolves like

Organic compounds are not expected to be soluble in water

Rule of Thumb: C/O ratio


Solubility

However,

If the organic compound can be ionized

It is more likely to be water-soluble

since ionic compounds are polar, and thus water-soluble

Requirement: the presence of an ionizable atom/group

What is an ionizable atom/group

one which can form a conjugate acid or conjugate base upon treatment with an acid or base


Solubility

Classification of Organic Compounds

from a solubilitypoint of view



Solubility

Phenols have very different acid-base properties

compared to alcohols

a phenolate, the conjugate base of a phenol, is much more stable than an alkoxide

phenolate

the conjugate base of an alcohol

alkoxide



Solubility

extensive charge delocalization into the aromatic ring

electron/charge delocalization is a stabilizing factor

more stable weaker conjugate base

the conjugate base of a stronger acid is a weaker conjugate base

thus a phenols is a stronger acid than an alcohol


Solubility

all insoluble with water if C/O ratio > 4

not strongly basic enough

to ionize in the presence of NaOH (aq) (remember why not)

But oxygen will protonate upon treatment with H2SO4 (conc)


Solubility

Samples to be tested

N-ethylaniline

a-naphthol (a phenol)

benzoic acid

butanol

para-dichlorobenzene