Chapter 6 Alkyl Halides Alcohols Amines Ethers and

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

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

Alcohol Nomenclature 2 -pentanol hydroxyl group 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)

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

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

Alternative Amine Nomenclature 2 -pentanamine amino group 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)

Amine Nomenclature Figure 6. 29 primary amine secondary amine tertiary amine ammonium ion

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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 propoxy group

Thiol Nomenclature 2 -pentanethiol mercapto group 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

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

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

Solvation

Acid-Base Properties of Alcohols p. Ka R=H -1. 74 15. 7 R = CH 3 -2. 2 15. 5 R = CH 2 CH 3 -1. 9 15. 9 R = C(CH 3)3 -2. 6 17

Acid-Base Properties of Amines Amine p. Ka 9. 24 10. 63 10. 78 9. 80

Activation of Alkyl Halides

Nitrogen Inversion

Nitrogen Inversion