The document discusses the nomenclature, preparation, and properties of ethers. There are two systems for naming ethers - the common system names them based on the groups bonded to oxygen, while IUPAC names the larger alkyl group as the parent and the smaller group as a prefix. Ethers can be prepared through Williamson's synthesis from alcohols, by reaction of alkyl halides with silver oxide, or by dehydration of alcohols. Ethers are colorless, highly flammable, and good solvents but are resistant to oxidation and reaction with acids except for cleavage by HI or HBr.
The document discusses the nomenclature, preparation, and properties of ethers. There are two systems for naming ethers - the common system names them based on the groups bonded to oxygen, while IUPAC names the larger alkyl group as the parent and the smaller group as a prefix. Ethers can be prepared through Williamson's synthesis from alcohols, by reaction of alkyl halides with silver oxide, or by dehydration of alcohols. Ethers are colorless, highly flammable, and good solvents but are resistant to oxidation and reaction with acids except for cleavage by HI or HBr.
The document discusses the nomenclature, preparation, and properties of ethers. There are two systems for naming ethers - the common system names them based on the groups bonded to oxygen, while IUPAC names the larger alkyl group as the parent and the smaller group as a prefix. Ethers can be prepared through Williamson's synthesis from alcohols, by reaction of alkyl halides with silver oxide, or by dehydration of alcohols. Ethers are colorless, highly flammable, and good solvents but are resistant to oxidation and reaction with acids except for cleavage by HI or HBr.
The document discusses the nomenclature, preparation, and properties of ethers. There are two systems for naming ethers - the common system names them based on the groups bonded to oxygen, while IUPAC names the larger alkyl group as the parent and the smaller group as a prefix. Ethers can be prepared through Williamson's synthesis from alcohols, by reaction of alkyl halides with silver oxide, or by dehydration of alcohols. Ethers are colorless, highly flammable, and good solvents but are resistant to oxidation and reaction with acids except for cleavage by HI or HBr.
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ETHERS
By: Dr Saima Najm
PhD Pharm. Chem. Assistant Professor L.C.P.S NOMENCLATURE COMMON SYSTEM OF NAMING ◦ In common system of naming ethers (simple and mixed), ethers are named by naming the two groups bonded to oxygen followed by the word ether. For example: ◦ CH3-O-CH3 Dimethyl ether ◦ C2H5-O-CH3 Ethyl methyl ether ◦ C2H5-O-C2H5 Diethyl ether ◦ C6H5-O-CH3 Phenyl methyl ether NOMENCLATURE IUPAC SYSTEM OF NAMING ◦ In IUPAC system, large alkyl group is take as parent molecule and given the last name (suffix) while the smaller alky group along with oxygen is used as a prefix and given the name ALKOXY (e.g methoxy, ethoxy, propoxy etc) ◦ CH3-O-CH3 Methoxy methane ◦ C2H5-O-CH3 Methoxy ethane ◦ C2H5-O-C2H5 Ethoxy ethane ◦ C6H5-O-CH3 Methoxy benzene PREPARATION OF ETHERS 1. WILLIAMSON’S SYNTHESIS (CONVERSION OF ALCOHOLS INTO ETHERS) The reaction of primary alcohol with sodium gives an alkoxide
2CH3CH2OH + 2Na 2CH3CH2O-Na+
Alkoxide when treated with RCl forms ether
CH3CH2O-Na+ + CH3CH2Cl CH3CH2-O-CH3CH2 + NaCl
2. REACTION OF ALKYL HALIDE WITH DRY SILVER OXIDE When alkyl halides are heated with dry silver oxide, ethers are produced.
2C2H5Br + Ag2O C2H5-O-C2H5 + 2AgBr
3. DEHYDRATION OF ALCOHOLS Ethers can be prepared by heating excess of alcohol with conc. H2SO4 at 140°C 2CH3CH2OH CH3CH2-O-CH3CH2 + H2O
When alcohols are of different types, then mixed ethers can be
prepared. 𝐶𝑜𝑛𝑐.𝐻2𝑆𝑂4 140 °𝐶
CH3OH + CH3CH2OH CH3-O-CH3CH2 + CH3-O-CH3 +
CH3CH2-O-CH3CH2 + H2O PHYSICAL PROPERTIES OF ETHERS 1. Ethers are colorless, highly inflammable compounds of low boiling points 2. Their chemical inactivity and their ability to dissolve fats, oil, gums and many more other organic compound make them very good solvent 3. Ethers are soluble in conc. sulfuric acid. This property is used as a distinguishing test between ethers and saturated hydrocarbons. 4. Lower ethers act as anesthetics 5. Ethers are lighter than water CHEMICAL PROPERTIES OF ETHERS
The ethereal O atom is a region of high electron density due to
lone pairs Ether O atom are Lewis bases, like an alcohol –OH group, the –OR group is a poor leaving group and needs to be converted to a better leaving group before substitution can occur. Resistance to Oxidations: Ethers are resistant to attack by the usual chemical oxidizing agent. Reagents like NH3, Na, alkali and acids have no action on ethers REACTION OF ETHER WITH HI AND HBr The most important reaction of ether is cleavage by acids such as HI and HBr
Reaction with HBr: The O atom of ether possess an unshared
electron pair which accepts a proton from HBr to form Oxonium ion. No further reaction takes place. R2O + HBr R2O+ -H + Br-
Reaction with HI: The O atom of ether accepts a proton from
HI to form oxonium ion, which reacts with I- to form R-OH and RI R2O + HI R2O+-H + + I- R2O+-H + + I- R-OH + RI