Ch. 9: Carboxylic Acid Derivatives + Ch. 10 Nitrogen and Phosophorus-Containing Compounds Flashcards
what are 3 carboxylic acid derivatives that we focus on on the MCAT?
- amides
- esters
- anhydrides
what is a commonality between how these three carboxylic acid derivatives are formed?
they are each formed by a condensation reaction with a carboxylic acid
defn: condensation reaction
a reaction that combines two molecules into one, while losing a small molecule
what is the small molecule that is lost in the condensation reactions that create amides, esters, and anhydrides? how does this molecule form?
water!
created from the hydroxyl group of the carboxylic acid and a hydrogen associated with the incoming nucleophile
general formula + naming scheme: amides
general formula: RCONR2
naming: replace the -oic acid with -amide
alkyl substituents on the nitrogen atom are listed as prefixes, and their location is specified with N-
how are amides generally synthesized?
by the condensation reaction of other carboxylic acid derivatives with either ammonia or an amine
what is required for the synthesis of amides to occur? what does that imply about what type of amines will undergo this reaction?
the loss of hydrogen from the nucleophile is required
only primary and secondary amines will undergo this reaction
defn + naming scheme: lactams
cyclic amides
named according to the carbon atom bonded to the nitrogen: Beta-lactams contain a bond between the beta-carbon and the N, gamma-lactams contain a bond between the gamma-carbon and the N, and so on
amides may or may not participate in hydrogen bonding, what does this depend on?
how does this affect their boiling points?
depends on the number of alkyl groups they have bonded, and therefore their boiling points may be lower or on the same level as the boiling points of carboxylic acids
defn + how are they formed + how are they named: esters
the dehydration synthesis products of other carboxylic acid derivatives and alcohol
named: by placing the esterifying group as a prefix
the suffix -oate replaces -oic acid
defn: esterifying group
the substituent bonded to the oxygen
defn: Fischer esterification
under acidic conditions, mixtures of carboxylic acids and alcohols will condense into esters
how else can esters be obtained?
from the reaction of anhydrides with alcohols
defn + naming scheme: lactones
cyclic esters
named in the same way as lactams: with the name of the precursor acid molecule also included
why do esters usually have lower boiling points than their related carboxylic acids?
because they lack hydrogen bonding
defn (bio and chem): triacylglycerols
the storage form of fats in the body
esters of long-chain carboxylic acids (fatty acids) and glycerol (1,2,3-propanetriol)
defn: saponification
the process by which fats are hydrolyzed under basic conditions to produce soap
what does subsequent acidification of the soap regenerate?
the atty acids
explain the process of saponification of a triacylglycerol
treat the triacylglycerol with NaOH to produce fatty acid salts (soap) as well as glycerol
how do anhydrides form?
they are the condensation dimers of 2 carboxylic acids
aka + general formula: anhydride
aka: acid anhydride
general formula RC(O)OC(O)R
how are symmetrical anhydrides named? how are asymmetrical anhydrides named?
symmetrical: named by substituting the word anhydride for the word acid in a carboxylic acid
asymmetrical: name the two chains alphabetically, followed by anhydride
what are phthalic and succinic anhydrides?
cyclic anhydrides arising from intramolecular condensation or dehydration of diacids
how are acid anhydrides synthesized?
two molecules of a carboxylic acid come together and lose a molecule of water