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MCAT Org. Chem Ch. 8

TermDefinition
Carboxylic Acids Contain: A carbonyl and a hydroxyl group connected to the same carbon. They are always terminal groups.
Suffix For Carboxylic Acids: -oic acid
Suffix For Salts Of Carboxylic Acids -oate
Suffix For Salts Of Dicarboxylic Acids -dioic acids
Carboxylic Acids Are: Polar and hydrogen bond very well, which results in high boiling points.
Carboxylic Acids Often Exist As: Dimers in solution
The Acidity Of A Carboxylic Acid Is Enhanced By: The resonance between its oxygen atoms. This can be further enhanced by substituents that are electron withdrawing and decreased by substituents that are electron-donating.
β-dicarboxylic acids Have A α-hydrogen That Is: Highly acidic
Carboxylic Acids Can Be Made By: The oxidation of primary alcohols or aldehydes using an oxidizing agent like potassium permanganate (KMnO4)
First Two Steps Of The Nucleophilic Acyl Substitution (Reaction In Carboxylic Acids): A nucleophile attacks the electrophilic carbonyl carbon, which opens the carbonyl and forms a tetrahedral intermediate. The carbonyl reforms and kicks off the leaving group.
Nucleophilic Acyl Substitution Rxn Continued: If the nucleophile is ammonia or an amine An amide is formed. Amides are given the suffix, -amid. Cyclic amides are called lactams.
Nucleophilic Acyl Substitution Rxn Continued: If the nucleophile is an alcohol: An ester is formed. Esters are given the suffix: -oate. Cyclic esters are called lactones.
Nucleophilic Acyl Substitution Rxn Continued: If The Nucleophile Is Another Carboxylic Acid: An anhydride is formed. Both linear and cyclic anhydrides are given the suffix anhydride.
Carboxylic Acids Can Be Reduced To A Primary Alcohol With: A strong reducing agent like lithium aluminum hydride (LiAlH4). Aldehyde intermediates are formed but are also reduced to primary alcohols.
Sodium Borohydride (NaBH4) Is: A common reducing agent for other organic reactions, but is not strong enough to reduce a carboxylic acid
β-Dicarboxylic Acids And Other β-keto Acids Can Undergo: Spontaneous decarboxylation when heated, losing a carbon as carbon dioxide. This reaction proceeds via a six-membered cyclic intermediate.
Mixing Long-Chain Carboxylic Acids (Fatty Acids) With A Strong Base Results In: The formation of salt called soap. The process is called saponification.
Soaps Contain: A Hydrophilic carboxylate head and hydrophobic alkyl chain tail
Soaps Organize In Hydrophilic Environments To Form: Micelles.
A Micelle Dissolves: Nonpolar organic molecules in its interior and can be solvated with water due to its exterior shell of hydrophilic groups.
Created by: SamB91