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Chapter 6

Chapter 6. Alkyl Halides, Alcohols, Amines, Ethers, and Their Sulfur-Containing Relatives. Nomenclature. Phenyl. Alkane. Carboxylic Acid. Alkene. Alcohol. Alkyne. Ether. Cycloalkane. Amine. Halide. Thioether. Thiol. Alcohol Nomenclature. hydroxyl group. 2-pentanol.

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Chapter 6

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  1. Chapter 6 Alkyl Halides, Alcohols, Amines, Ethers, and Their Sulfur-Containing Relatives

  2. Nomenclature Phenyl Alkane Carboxylic Acid Alkene Alcohol Alkyne Ether Cycloalkane Amine Halide Thioether Thiol

  3. Alcohol Nomenclature hydroxyl group 2-pentanol 1) Find the longest carbon chain containing the alcohol 2) Start numbering from the end closest to the alcohol 3) Finish with -ol as the suffix (takes priority over -ene & -yne)

  4. Alcohol Nomenclature 1,2-ethanediol 1,2,3-propanetriol ethylene glycol glycerine

  5. Amine Nomenclature methylpropyl amine 1) Name all of the substituents coming off the nitrgoen (ignore hydrogens) 2) Place them in alphabetical order add a space then amine Best way to name amines until the structures become too complicated

  6. Alternative Amine Nomenclature amino group 2-pentanamine 1) Find the longest carbon chain containing the amine 2) Start numbering from the end closest to the amine 3) Finish with -amine as the suffix (does NOT take priority over -ol, -ene, or -yne)

  7. Amine Nomenclature Figure 6.29 primary amine secondaryamine tertiaryamine ammonium ion

  8. Top 3 Selling Drugs in the US Plavix Lipitor Advair (Salmeterol)

  9. Ether Nomenclature methylpropyl ether 1) Name both substituents coming off the oxygen 2) Place them in alphabetical order add a space then ether methoxy group ethoxy group propoxy group

  10. Thiol Nomenclature mercapto group 2-pentanethiol 1) Find the longest carbon chain containing the thiol 2) Start numbering from the end closest to the thiol 3) Name normally then add thiol to the end disulfide

  11. Thioether Nomenclature methylpropyl sulfide 1) Name both substituents coming off the sulfur 2) Place them in alphabetical order add a space then sulfide

  12. Solvents in Organic Chemistry Adapted from: Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; New York: Harper & Row, 1987.

  13. Solvation

  14. Acid-Base Properties of Alcohols pKa pKa -1.74 15.7 R = H 15.5 R = CH3 -2.2 -1.9 15.9 R = CH2CH3 R = C(CH3)3 17 -2.6

  15. Acid-Base Properties of Amines Amine pKa 9.24 10.63 10.78 9.80

  16. Activation of Alkyl Halides

  17. Nitrogen Inversion

  18. Nitrogen Inversion

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