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Organic Chemistry Oxygen and Sulfur in Organic Compounds

Organic Chemistry Oxygen and Sulfur in Organic Compounds. Chapter 12 Part 06 Ethers. Page 104. Ar. Ar. O. O. R. Ar. H. R. O. O. H. R. 1. Ethers - contain the R-O-R functional group - the –OR group is termed alkoxy

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Organic Chemistry Oxygen and Sulfur in Organic Compounds

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  1. Organic Chemistry Oxygen and Sulfurin Organic Compounds

  2. Chapter 12Part 06Ethers Page 104

  3. Ar Ar O O R Ar H R O O H R 1. Ethers -contain the R-O-R functional group - the –OR group is termed alkoxy - derivatives of water where both hydrogens are replaced by R groups

  4. R O R’ R O R 2. Classification -can be symmetrical or unsymmetrical - symmetrical ethers contain two identical R groups - unsymmetrical ethers contain two different R groups

  5. 3. Nomenclature - IUPAC - Determine main chain (longest continuous chain that does NOT contain the –OR group - Identify the remaining short chain as an alkoxy group CH3O is methoxy C2H5O is ethoxy, etc. - Number the chain so the C to which the –OR is attached has the lowest number - Place the name of the alkoxy group in front of the name of the main chain indicate the position of the alkoxy group on the main chain with a number

  6. 3. Nomenclature - Common - Identify the 2 substituents, either alkyl or aryl, attached to the ether linkage. - Name the substituents alphabetically followed by the word ether - If the ether is symmetrical (2 substituents are the same), the prefix di- is used

  7. 3. Nomenclature Name the following ethers by either the IUPAC system or the common name. Indicate if it is symmetrical or unsymmetrical.

  8. H H H H H H H O C C C C H C C H C H H H H H H H IUPAC Ethoxypentane Ethylpentyl ether Unsymmetrical

  9. H H H H O C C H C H C H H H H IUPAC Ethoxyethane Diethyl ether - “ether” Symmetrical

  10. H H H H H C C O H C C H C H H H H H IUPAC Methoxybutane Butylmethyl ether Unsymmetrical

  11. H H H O C C H C H H H IUPAC Propoxycyclopentane Cyclopentylpropyl ether Unsymmetrical

  12. O Phenoxybenzene Diphenyl ether Symmetrical

  13. O Cyclohexylphenyl ether Cyclohexoxy benzene Unsymmetrical

  14. H H O C H IUPAC methoxy benzene Methylphenyl ether: anisole Unsymmetrical

  15. Properties and Uses • - prepared from dehydration of 2 alcohols • - colorless, • - slightly soluble in water • - very soluble in organic solvents • - density & boiling points similar to hydrocarbons of similar mass

  16. Properties and Uses • - largely unreactive (stable in acids and bases; resistant to oxidizing and reducing agents) • - excellent solvents for chemical reactions • - highly flammable • - form explosive organic peroxides on standing • Diethyl ether and tetrahydrofuran – most widely used organic solvents

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