I. Competition Between Substitution and Elimination
a. Conditions that favor SN2 reactions also favor E2 reactions; conditions
that favor SN1 reactions also favor E1 reactions.
b. First decide whether the conditions favor SN2/E2 or SN1/E1. Then decide
I. The Hydrolysis of Nitriles
a. Nitriles are hard to hydrolyze, but they can by slowly hydrolyzed into
carboxylic acids when heated with water and an acid.
b. First the acid protonates the cyano group of the nitrile, making it easier for
water to add to
I. Reactions of Amides
a. Amides are very unreactive.
b. Amides dont react with halide ions, carboxylate ions, alcohols, or water
because these nucleophiles are weaker than the leaving group of an amide.
c. Amides react with water and alcohols if the reac
I. Soaps, Detergents, and Micelles
a. Fats and oils are triesters of glycerol.
b. When the ester groups of a fat or oil are hydrolyzed in a basic solution,
glycerol and carboxylate ions form.
c. Long chained unbranched carboxylic acids that come off of fa
I. Acid-Catalyzed Ester Hydrolysis and Transesterification
a. Acid or the hydroxide ion can be used to catalyze the rate of ester
a.i. In these reactions all organic intermediates and products in acidic
solution are positively charged or neutr
I. The Reactions of Acid Anhydrides
a. Acid anhydrides dont react with sodium chloride or sodium bromide
because those bases are weaker than the departing carboxylate ion.
b. Anhydrides react with water to form two equivalents of a carboxylic acid.
I. How Class I Carbonyl Compounds React
a. The reactivity of carbonyl compounds is due to the polarity of the C=O
a.i. Since the carbon is electron deficient, it will be attacked by
a.ii. When the nucleophile adds, the weakest bond of
I. The Structures of Carboxylic Acids and Carboxylic Acid Derivatives
a. The carbonyl carbon in carboxylic acids and carboxylic acid derivatives is
a.i. The three atoms attached to the carbonyl carbon are in a plane.
b. The carbonyl oxygen
I. Functional Groups in Bio-molecules
a. The carbonyl group (oxygen doubled bonded to a carbon) is the most
important functional group.
b. An acyl group is a carbonyl group bonded to an alkyl or aryl group.
c. Class I carbonyl compounds are those with an
I. This requires dehydration by P2O5. How Cells Activate Carboxylic Acids
a. Acyl halides and acyl anhydrides are too reactive to be used in biological
a.i. They would quickly hydrolyze since cells have so much water.
b. Biological organisms acti