Carboxylic Acid Derivatives (9)

Amides

are the condensation products of carboxylic acids and ammonia or amines

-amide; N-

amides are given the suffix _____. The alkyl groups on a substituted amide are written at the beginning of the name with the prefix ______

Lactams

Cyclic amides; they are named by the Greek letter of the carbon forming the bond with the nitrogen (beta-lactam, gamma-lactam, and so on)

Esters

are the condensation products of carboxylic acids with alcohols (Fischer esterification)

-oate

esters are given the suffix _____. The esterifying group is written as a substituent, without a number

Lactones

cyclic esters; these are named by the number of carbons in the ring and the Greek letter of the carbon forming the bond with the oxygen (alpha-acetolactone, beta-propiolactone, and so on)

Triacylglycerols

a form of fat storage, include three ester bonds between glycerol and fatty acids

Saponification

is the breakdown of fat using a strong base to form soap

Soap

salts of long-chain carboxylic acids

Anhydrides

are the 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

Esters; Amides

in nucleophilic substitution reactions, anhydrides are more reactive than ________, which are more reactive than ________

Steric Hindrance

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

Protecting Groups

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

Induction

refers to uneven distribution of charge across a sigma bond because of differences in electronegativity

Greater

the more electronegative groups in a carbonyl-containing compound, the _________ its reactivity

Conjugation

refers to the presence of alternating single and multiple bonds, which creates delocalized pi electron clouds above and below the plane of the molecule

Resonance

electrons experience _________ through the unhybridized p-orbitals, increasing stability

More

conjugated carbonyl-containing compounds are more reactive because they can stabilize their transition states

Increased

_________ strain in a molecule can make it more reactive

beta-lactams

are prone to hydrolysis because they have significant ring strain

Ring Strain

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

Cleaved

anhydrides can be ________ by the addition of a nucleophile

Ammonia or Amine

addition of this results in an amide and a carboxylic aid

Alcohol

addition of this results in an ester and a carboxylic acid

Water

addition of this results in two carboxylic acids

Transesterification

is the exchange of one esterrifying group for another on an ester. The attacking nucleophile is an alcohol

Amides

can be hydrolyzed to carboxylic acids under strongly acidic or basic conditions. The attacking nucleophile is water or the hydroxide anion