Flashcards in ch 8 - Carboxylic Acids Deck (22)
contain both carbonyl and hydroxyl group bonded to the same carbon; always terminal
naming carboxylic acids
when priority group, add -oic acid to parent chain and the carbon it is attached to becomes carbon 1.
when in a chain: list the cycloalkane and add "carboxylic acid" at the end. Salts of carboxylic acids are named with the cation followed by -oate; molecules with a carboxylic group on each end are named by adding suffix -dioic acid
pairs of molecules connected by two hydrogen bonds
dicarboxylic acids in which each carboxylic acid is positioned on the beta-carbon of the other (two carboxylic acids separated by a single carbon)
synthesis of primary alcohol to carboxylic acid
use KMnO4 (secondary and tertiary ETOh cannot be synthesized to carboxylic acids)
Nucleophilic Acyl Substitution
similar to nucleophilic addition to an aldehyde or ketone except for the presence of a leaving group in this reaction; nucleophile opens up to the carbonyl, forms a tetrahedral intermediate, and then the carbonyl reforms, kicking off the leaving group; nucleophilic molecule replaces the leaving group of an acyl derivative
all molecules with a carboxylic acid-derived carbonyl, including carboxylic acids, amides, esters, anhydrides and others.
acyl derivatives focused on by the mcat
carboxylic acids, amides, esters, anhydrides
R-double bond O-C-N-R'
formation of amide from carboxylic acid
driven by ammonia (NH3) or an amine (NH2-R)
named by replacing the -oic acid suffix of carboxylic acid with -amide; any alkyl groups on the nitrogen are placed at the beginning of the name with the prefix N-. Has resonance with the double bond changing from the O-C to C-N bond.
cyclic amides named by replacing the -oic acid of the parent carboxylic acid with -lactam; also named by indicating the specific carbon that is bonded during cyclization of the compound
hybrid between a carboxylic acid and an ether (ROR'), can be made by reacting carboxylic acids with alcohols under acidic conditions
condensation reaction with water a side product; occurs most rapidly with primary alcohols
name alkane chain beside oxygen (ex ethyl) and then add -oate as suffix to parent alkane on other side with carboxyl
esters that are cyclic; named by replacing -oic acid with -lactone
ex. R-C(double bond)O and O connected to C(double bond) O and R'
formed by the condensation of two carboxylic acids; named by replacing the acid at the end of the name of the parent carboxylic acid with anhydride; same with cyclic; occurs via nucleophilic acyl substitution
Reduction of carboxylic acids to primary alcohol
reduced by LiAlH4, sometimes with aldehyde as an intermediate; occurs by nucleophilic addition of hydride to the carbonyl group
complete loss of carboxyl group as CO2
process by which a long-chain carboxylic acid reacts with sodium or potassium hydroxide and forms a salt; occurs by mixing fatty acids with lye (sodium or potassium hydroxide), resulting in formation of salt known as soap