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ch17 Material Type: Notes; Professor: Hatton; Class: Organic Chemistry II; Subject: Chemistry; University: George Mason University; Term: Spring 2011;
Typology: Study notes
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About The Authors These PowerPoint Lecture Slides were created and prepared by Professor William Tam and his wife, Dr. Phillis Chang. Professor William Tam received his B.Sc. at the University of Hong Kong in 1990 and his Ph.D. at the University of Toronto (Canada) in
2. Nomenclature and Physical Properties Nomenclature of Carboxylic Acids and Derivatives ● (^) Rules Carboxylic acid as parent (suffix): ending with “–oic acid” (^) Carboxylate as parent (suffix): ending with “– oate”
Examples Sodium benzoate Ethanenitrile O Na
Cl
Benzoyl chloride H 3
Ch. 17 - 8 2C. Acidity of Carboxylic Acids O R O
pK a ~ 4- Compare ● pK a of H 2 O ~ 16 ● pK a of H 2 CO 3 ~ 7 ● pK^ of HF ~ 3
1
3
1
2
3
CH 3
2
(^) The conjugate base B 1 is more stable (the anion is more delocalized) than B 2 due to resonance stabilization O CH 3
3
3
● Thus, A 1 is a stronger acid than A 2
2
Acidity of Carboxylic Acids, Phenols and Alcohols O
3
O
Acidity of Carboxylic Acids, Phenols and Alcohols O H
O O O O
Question
If you are given three unknown samples: one is benzoic acid; one is phenol; and one is cyclohexyl alcohol; how would you distinguish them by simple chemical tests? ● (^) Recall: acidity of O
O R O H Na^ OH
O R O Na
pKa^0.^70 1.^48 O OH Cl Cl Cl O OH H Cl Cl O OH H H Cl O OH H H H
^ >
Stability of conjugate bases O O Cl Cl Cl O O H Cl Cl
O O H H Cl
O O H H H
Ch. 17 - 4 - Chlorobutanoic acid ( pK a
Cl 2 - Chlorobutanoic acid ( pK a
Cl 3 - Chlorobutanoic acid ( pK a
Cl
^ >