Solubility behavior of organic compounds

Dotsha J. Raheem Muslih S. Hamasharif College of Science Department of Chemistry

1. Solubility (definition) 2. Information obtained from solubility 3. Types of solubility 4. Factors affecting solubility 5. Water soluble compounds

Solubility ( definition)
The amount of solute needed to form a solution in a given quantity of solvent. Soluble if it dissolves to the extent of (3.3g/ 100 ml ) of solvent

Information obtained from solubility

i. Presence of a functional group.
Because hydrocarbons are insoluble in water, observing that an unknown is partially soluble in water indicates that a polar functional group is present.

ii. Solubility in certain solvents often leads to more specific information about functional group.

iii. Certain conclusions about molecular size and composition may sometimes be made from solubility tests.

CH3(CH2)nCH2OH
monofunctional compounds

If ( n) higher than 5 is water insoluble If ( n) fewer than 5 is water soluble

types of solubility
The solubility of organic compounds can be divided into two categories:

e.g. benzoic acid dissolves in 5% NaOH but not in H2O Utilized for identification of functional groups

e.g. CHCl3 in C2H5-O-C2H5 To determine solvents for chemical reactions and purification (as in recrystallization)

Factors affecting solubility

1-Temperature: A-if the solution process absorbs energy then the solubility will be increase with increasing temperature. B-if the solution process releases energy then the solubility will decrease with increasing temperature.

Factors affecting solubility

2-Polarity:
Like dissolves like

 Polar compounds dissolve in polar solvents

H
CH3NH2
methyl amine

H2O
water

O H H

H
Hydrogen bonding

CH3 N

Ionic compounds dissolve in polar solvents.

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 non polar compounds dissolve in non polar solvents e.g. Iodine(I2)is a (non polar) and soluble in non polar solvents like carbon tetrachloride(CCl4).

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Factors affecting solubility

3-Molecular Size:
In general, an increases in molecular weight leads an increase in intermolecular forces and decreased solubility.

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Q//What are the intermolecular forces? Q//What is the relation between melting point and solubility

Factors affecting solubility

4-Effect of chain branching on solubility. 1-Compounds having a branched chain are more soluble than the corresponding straight-chain compound (branching lowers intermolecular forces and decreases intermolecular attraction).

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2-The position of the functional group in the carbon chain also affects solubility.

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Water soluble compounds

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Solubility in H2O
When a compound dissolves in water, its expected to be: - Low M. wt. compound - Polar - ionic

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A compound soluble in H2O and in ether

SA: Acids (carboxylic) SB: Bases (amines) S1: Neutral compounds (alcohols, aldehydes, ketones, esters) General characteristics: - Polar (non ionic) - Contain 5 or less C atoms - Has a functional group that is polar and capable of forming H-bonds
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A compound soluble in H2O but not in ether

S2: Salts of organic acids (RCO2Na, RSO3Na), amine hydrochlorides (RNH3Cl), amino acids, carbohydrates, polyhydroxy compounds and polybasic acids. General characteristics: - Ionic ( a salt) - Contain two or more polar groups but not more than 4C atoms per functional group
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