Flashcards in Organic Chemistry Chapter 9: Carboxylic Acid Derivatives Deck (27)
the condensation produce of carboxylic acids and ammonia or amines
What are the alkyl group on a substituted amide denoted with?
Cyclic amides are called
lactams - named by the greek letter of the carbon forming the bond with the nitrogen
condensation products of carboxylic acids with alcohols (fisher esterification)
lactones - named by the number of carbons in the ring and the Greek letter of the carbon forming the bond with the oxygen.
form of fat storage that contain three ester bonds between glycerol and fatty acids
breakdown of fat using a strong base to form soap (salts of long-chain carboxylic acids)
condensation dimers of carboxylic acids
Symmetric anhydrides are named for:
the parent carboxylic acid, followed by anhydride
Asymmetric anhydrides are named:
by listing the parent carboxylic acids alphabetically, followed by anhydride.
How can cyclic anhydrides be synthesized?
By heating dioic acids. Five or six-membered rings are generally stable.
In nucleophilic substitution reactions, which is most reactive?
Anhydride, amides, esters
Anhydride, esters, amides
describes when a reaction cannot proceed (or significantly slows because of substituents crowding the reactive site.
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 sigma 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 pi electron clouds above and below the plane of the molecule.
experienced through the unhybridized p-orbitals, increasing stability. Conjugated carbonyl-containing compounds are more reactive because they can stabilize their transition states.
Increased strain can
make it more reactive (ex. B-lactams are prone to hydrolysis because they have significant ring strain.
is due to torsional strain from eclipsing interactions and angle strain from compressing bond angles below 109.5
How can anhydrides be cleaved?
an addition of a nucleophile.
Anhydride + ammonia or amine
results in an amide and a carboxylic acid
Anhydride + alcohol
ester and a carboxylic acid
Anhydride + water
2 carboxylic acids
exchange of one esterifying group for another on an ester. The attacking nucleophile is an alcohol.