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

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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

phenolate

But


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

no charge delocalization here


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


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