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Chapter 13/16: Alcohols, Ethers and Amines

Chapter 13/16: Alcohols, Ethers and Amines. Suggested Problems: Chapter 13:3-12,14,25,26,39,40, 43(a-c), 44( a,b ) Chapter 16 : 3,4,6,7-15. Functional Groups Based on Water. Replacing one hydrogen on water by an organic group affords an alcohol R-O-H

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Chapter 13/16: Alcohols, Ethers and Amines

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  1. Chapter 13/16: Alcohols, Ethers and Amines Suggested Problems: Chapter 13:3-12,14,25,26,39,40, 43(a-c), 44(a,b) Chapter 16: 3,4,6,7-15

  2. Functional Groups Based on Water • Replacing one hydrogen on water by an organic group affords an alcohol R-O-H • Replacing the second hydrogen on water by an organic groups yields an ether R-O-R’

  3. N N N H H R R R R H R R Functional Groups Based on Ammonia • Replacing one or more hydrogens on ammonia (NH3) gives an organic amine

  4. Alcohols • The functional group of an alcohol is the hydroxyl group • The generic formula of an alcohol is R-OH CH3-CH2-OH ethanol ethyl alcohol

  5. Naming Alcohols • IUPAC: • Follow the normal rules • Add the suffix ‘-ol’ to the parent chain • Give the OH group the lowest number • Or, for very simple alcohols • Name the alkyl group and call it an alcohol • This is a common name

  6. Examples

  7. Examples

  8. Examples • 4-methyl-2-hexanol 1,2-dibromo-2-butanol

  9. Example • Aromatic alcohols are called phenols (from phenyl alcohol)

  10. Primary Alcohols • Primary alcohols have one carbon group bonded to the C with the OH • Name:

  11. Secondary Alcohols • Secondary alcohols have two carbon groups bonded to the C with the OH • Name:

  12. Tertiary Alcohols • Tertiary alcohols have three carbon groups bonded to the C with the OH • Name:

  13. Ethers • The functional group of an ether is an oxygen bridging two alkyl groups • The generic formula of an ether is R-O-R’ CH3-CH2-O-CH2-CH3 diethyl ether

  14. Naming Ethers • Name each alkyl group and call it an ether • Give names in alphabetical order if needed • Each alkyl group is treated as a separate word • This is a common name

  15. Examples ethyl methyl ether methyl phenyl ether

  16. Amines • The functional group of an amine is a nitrogen bonded to 1, 2 or 3 alkyl groups • The generic formula of an amine is R-NH2or R2NH, or R3N CH3-NH2 methylamine

  17. Naming Amines • Name the alkyl groups and call it an amine by tacking amine to the end of the name Isopropylamine trimethylamine

  18. Reactions of Alcohols • One characteristic reaction of alcohols is oxidation • In organic chemistry, ‘oxidation’ means • adding bonds between C and O or • removing bonds between C and H

  19. Oxidation of Primary Alcohols • Primary alcohols are oxidized to aldehydes

  20. Oxidation of Secondary Alcohols • Secondary alcohols are oxidized to ketones • Tertiary alcohols are not oxidized • Carbon can not have five bonds

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