Carboxylic Acid Derivatives

condensation products of carboxylic acids and ammonia or amines

condensation products of carboxylic acids with alcohols (Fischer Esterification)

condensation dimers of carboxylic acids

order of reactivity of carboxylic acid derivatives in nucleophilic substitution reactions

describes when a reaction cannot proceed (or significantly slows) because of substituents crowding the reactive site

groups, such as acetals, that can be used to increase steric hindrance or otherwise decrease the reactivity of a particular portion of a molecule

refers to uneven distribution of charge across a σ bond because of differences in electronegativity; the more electronegative groups in a carbonyl-containing compound, the greater its reactivity

refers to the presence of alternating single and multiple bonds, which creates delocalized π electron clouds above and below the plane of the molecule; electrons experience resonance through the unhybridized p-orbitals, increasing stability; conjugated carbonyl containing compounds are more reactive because they can stabilize their transition state

increased amounts can make a molecule more reactive; β-lactams are prone to hydrolysis because they have significant ring ____

is due to torsional strain from eclipsing interactions and angle strain form compressing bond angles below 109.5°

splits an anhydride in two by the addition of a nucleophile

cleavage reaction: nucleophile thats addition results in an amide and a carboxylic acid

cleavage reaction: nucleophile thats addition results in an ester and a carboxylic acid

cleavage reaction: nucleophile thats addition results in two carboxylic acids

the exchange of one esterifying group for another on an ester; the attacking nucleophile is an alcohol; one ester is simply transformed into another one

can be hydrolyzed to carboxylic acids under strongly acidic or basic conditions; the attacking nucleophile is water or the hydroxide ion