Orgo I Experiments I-3

Partition Coefficient

ratio of solubility in organic phase to aqueous phase

K > 1 is more soluble

in organic

Liquid Liquid Extraction

between two immiscible liquids

O-H bond has

partial ionic character

Branched chains have better

solubility than straight chains

Upper layer is

the less dense layer

Diethyl is

less dense than water → upper layer

Methylene is

more dense than water → bottom layer

Diethyl ether forces

dipole dipole

9-Fluorenone Nonpolar

induced dipole-induced dipole,

9-Fluorenone Polar

hydrogen bonding, dipole-induced dipole, dipole-dipole

Concentrate organic layer

in the heating block

9-Fluorenone is

more soluble in the organic layer; and less dense than water

The salt of benzoic acid

is highly ionic; very soluble in water and not in diethyl ether

Benzoic contains ionic bonds between

carboxylic group and sodium ion

Benzoic Acid used

in place of 9-Fluorenone

Sodium Bicarbonate used

instead of water

Benzoic Acid is polar

due to Hydrogen bonding

Benzoic Acid is more polar

than 9-Fluorenone

Benzoic Acid amount is higher

in aqueous than organic

Sodium Benzoate is

more polar than everything

Amount in organic is less

with Benzoic rather than 9-Fluoenone

Separatory funnel is

better for determining partition coefficient

Glass pipet used

NOT filter pipet

No test for

carboxylic acid

pH affects

the solubility of organic acids

P-nitrobenzoic and p-chloroaniline are

both soluble in inorganic before NaOH and HCl, after they are both soluble in diethyl but p-chloroaniline is not soluble in water

The solvents must have

a favorable distribution coefficient and not react chemically for the components to be separated

Some organic compounds can be

reversibly chemically altered to become soluble in water

Organic Acids include

carboxylic acids (strong) and phenols (weak)

Can be converted to

their salt when combined with an inorganic base

Salts are soluble in

water, but not in organic solvents

Organic bases include

amines

COOH + NaOH

salt

COOH ionized by

NaHCO3

Phenols cannot be deprotonated by

sodium bicarbonate

Amines + HCl

salt

Ammonium Ion

not soluble in ether, soluble in water

Top should be open

while draining

Amine, Phenol, and Carboxylic Acid

are soluble in organic solvents