Ch. 9: Carboxylic Acid Derivatives Flashcards
how are amides, esters, and anhydrides all formed
condensation reactions with carboxylic acids
what are amides
carbonyl with alpha nitrogen
RCONR2
what kind of amines will form amides with a carboxylic acid
primary and secondary only, amine must lose a hydrogen
what are cyclic amides called
lactams
what are esters
carbonyl with alpha ether
RCOOR
what occurs during a fischer esterification
acidic conditions: carboxylic acids + alcohols –> esters
what are cyclic esters called
lactones
carboxylic acid vs ester boiling point
carboxylic acid > esters
esters cannot hydrogen bond
carboxylic acid vs amides boiling point
???
hydrogen boding depends on number of alkyl groups present
what functional group links carboxylic acids and glycerol
esters
triacylglycerols are formed by esters of long chain carboxylic acids (fatty acids) and glycerols
what occurs during saponification
fats are hydrolyzed to produce soaps
[rCOO- + Na]
how are anhydrides formed
carboxylic acid condensation
RCO + RCO
carboxylic acid vs anhydride
carboxylic acid < anhydride
anhydrides must have a much greater weight than their carboxylic acid derivatives
what are cyclic anhydrides called
phthalic or succinic anhydrides
ordered reactivity of amides, anhydrides, carboxylic acids, and esters to nucleophilic substitution
anhydrides > carboxylic acids = esters > amides
most electrophilic least electrophilic
what does induction refer to
distribution of charge across sigma bonds
electronegative atoms create partial positive charges on their adjacent atoms
what does conjugation refer to
alternating single and multiple bonds, delocalizing electrons throughout the entire pi system
what are enones
alpha, beta - unsaturated carbonyl system
conjugated carbonyl structure
what occurs during a cleavage reaction
molecule splits in two
what occurs during a nucleophilic acyl substitution of an anhydride
nucleophile (ammonia, alcohol) attacks one carbonyl (that acts as an electrophile) and the other carbonyl becomes the leaving group
what will revert an anhydride back to carboxylic acids
water
what occurs during transesterification
alcohol acts as an nucleophile that attacks an ester (acting as an electrophile) and one ester is transformed to another as the original -OR group leaves and is replaced with that of the nucleophile
what will revert an amide back to a carboxylic acid
acid to protonate (or base to attack) + water
