Diethyl ether or Ethoxy ethane is a colorless sweet liquid. Its molecular formula is CH3-CH2-O-CH2-CH3. Its IUPAC name is Ethoxyethane. For the laboratory preparation of diethyl ether, ethanol (ethyl alcohol) is dehydrated by using conc. H2SO4 at about 140 °C.
In lab, Diethyl ether is formed by heating excess of ethyl alcohol (ethanol) with conc. sulphuric acid. This process is carried out at about 140 °C.
This chemical change occurs in following two steps:
Sulphuric acid acts as dehydrating agent and it combines with ethyl alcohol to form ethyl hydrogen sulphate at about 110 °C.
Ethyl hydrogen sulphate reacts with another molecule of ethyl alcohol at about 140 °C to form diethyl ether.
About 100 ml of ethanol is kept in a round bottom flask. 50 ml of concentrated sulphuric acid is gradually added to ethanol with constant stirring. The flask is then fitted with a dropping funnel and a thermometer as shown in above figure. The mixture is then heated to about 140 °C for several minutes. Then the ether starts to distill over and is collected in a receiver at ice cold condition. For larger amount of yielding of diethyl ether, ethanol is added gradually from the dropping funnel.
Note: If the receiver is not kept at ice cold condition, diethyl ether may not condense to liquid form since the boiling point of nearly equal to room temperature (34.6 °C).
Purification and Dehydration
Thus formed diethyl ether contains many impurities including ethanol, S02, and water. Acidic impurities are removed by washing with NaOH and washing with water. Then it is dehydrated over anhydrous CaCl2. Finally, it is redistilled at about 34-36 °C.
General Properties of Diethyl Ether
Molecular mass: 74.12 g/mol
State: Liquid due to intermolecular H-bonding
Odor: Sweet smell
Solubility: Slightly soluble in water due to non-polar nature and presence of H-bonding
Formic acid is a weak organic acid. Its molecular formula is HCOOH. According to IUPAC, it is termed as methanoic acid. It is the simplest form of carboxylic acid. Since formic acid has antibacterial property, it is added in livestock feed to prevent the growth of bacteria. Although formic acid is generally weak in nature, it can be dangerous at higher concentration. It produces burns and blisters on the skin and injures the eyes and the mucous membranes in the mouth, throat, and respiratory system.
Then how is formic acid prepared in laboratory?
Laboratory preparation of formic acid involves the reaction of oxalic acid crystals with glycerol.
Formation of glycerol monoformate: Firstly, glycerol is treated with oxalic acid crystals at about 120oC or 393 K to form glycerol monoxalate. Glycerol monoxalate decomposes itself to give glycerol monoformate.
Hydrolysis of glycerol monoformate: The glycerol monoxalate thus formed reacts with fresh water [obtained from oxalic acid crystals, (COOH)2.2H2O] to produce formic acid.
In this reaction, glycerol is recovered back which can be used over again and again. Hence glycerol acts as catalyst.
The mixture of about 40 g oxalic acid crystal and 50 mL anhydrous glycerol is taken in a distillation flask which is placed over a sand bath. The flask is provided with the thermometer and the delivery tube is surrounded with a condenser. Upon heating the mixture at about 120oC, the reaction initiates with the evolution of CO2. When the evolution of CO2 stops, then the flask is cooled and fresh oxalic acid crystals are again added in the flask. The flask is again heated upto 120oC to form aqueous formic acid. Finally it is collected in reciever.
Laboratory Preparation of Formic Acid ( Methanoic Acid )
Preparation of anhydrous formic acid
Formic acid is soluble in water and forms aqueous formic acid during its preparation. Hence we must dehydrate it to get anhydrous formic acid in lab as follows:
The aqueous formic acid is first neutralized by lead carbonate (PbCO3) or litharge(PbO) to get lead formate. The solution of lead formate thus formed is filtered and concentrated to get lead formate crystals.
The crystals of lead formate are filled in the inner tube of condenser. One end of the condenser is fitted with hydrogen sulphide gas generator and the other end is fitted with a buchner flask guarded with a calcium chloride tube as shown in the above figure.
Conversion of aqueous formic acid into anhydrous formic acid
H2S gas is passed through he condenser while steam is passed through its outer jacket. The anhydrous formic acid collects into the buchner flask.
We cannot subject aqueous formic acid to fractional distillation to remove water because boiling point of formic acid is nearly equal to that of water. (Boiling point of water : 100oC; Boiling point of formic acid : 100.5oC)
Dehydrating agents like Conc. H2SO4, KOH, P2O5etc cannot be used as formic acid reacts with them.
General properties of formic acid
Molecular mass: 42.03 g/mol
State: Liquid due to intermolecular H-bonding
Odor: Sharp pungent smell
Solubility: Soluble in water and most of the polar organic solvents
Those compounds which are formed by combination of ions are called ionic compounds. They are also called electrovalent compounds. Electrostatic force of attraction between positively charged and negatively charged ions hold them together in the crystal lattice. The bond between oppositely charged ions in these compounds is called ionic bond or electrovalent bond.
Formation of Ionic Compounds
Before going through the properties of ionic compounds, lets look about their formation. Ionic compounds are formed by the combination of metal and non-metal. Metal atom loses electron whereas non metal atom gains electrons, and thereby both attain octet. The metal atom becomes positively charged after losing electron and non-metal atom becomes negatively charged after gaining electron. These charged species are called ions.
Being oppositely charged species, metal and non-metal ions attract each other with strong electrostatic force of attraction. This bond which is formed by the complete transfer of one or more electrons from one atom to other is called ionic bond and the compounds thus formed are called electrovalent or ionic compounds. Examples of ionic compounds are: NaCl, KCl, NaOH, CaCl2, HCl etc.
Let us see the formation of an ionic compound, NaCl as an example. Its formation takes place in following steps:
Sodium atom loses the outermost electron and becomes positively charged ion with octet. Na → Na+ + e–
Chlorine gains that electron, and becomes negatively charged with octet. Cl + e– → Cl–
Sodium and chloride ions are held together by electrostatic forces of attraction. Na+ + Cl– → Na+Cl or NaCl
Note: Electrovalency of an element is the number of electrons lost or gained by an atom of the element while forming an ionic bond.In above example, elecrtovalency of sodium and chlorine is 1
Properties of Ionic Compounds
High melting and boiling point:
Ionic compounds have high melting and boiling points. Since the constituents of ionic compounds are held together by strong electrostatic force of attraction, they require large amount of energy to dissociate.
Ions in ionic compounds are arranged in regular three dimensional pattern called crystal lattice. Ions are oriented in fixed direction and placed in fixed place unlike amorphous solid.
Hard and Brittle:
Since force of attraction between ions is very high ionic compounds are hard in nature. Also, due to the formation of crystal lattice, these are generally brittle in nature and break into pieces on strong hitting.
High enthalpy of fusion and vaporization:
Enthalpy of fusion is the amount of energy required to change one mole of solid into its liquid form at its melting point. Similarly, enthalpy of vaporization is the amount of energy required to change one mole of liquid into its vapour form at its boiling point. Due to the strong electrostatic force acting on ions, they require high energy to dissociate and have high enthalpy of fusion and vaporization.
Although ionic solids consists of ions, they do not conduct electricity due to immobility of ions. But in solution form, ions change into electrolytes and conduct electricity. However, electrolytic solution have low conductivity than that of metals.
Ionic solids are generally soluble in polar solvent like water and are insoluble in non polar solvent like benzene.