11: Carboxylic Acids and Its Derivatives (Part 2) Flashcards
The closer the electron-withdrawing group to the ________, the stronger the acid.
COOH
these can be prepared from carboxylic acid
carboxylic acid derivatives
these are called lactones
cyclic esters
Groups that donate electron density ____________ a benzene ring towards electrophilic attack and make a benzoic acid less acidic
activate
As the basicity of Z increases, the stability of RCOZ increases because of added ____________________________
resonance stabilization
these groups make a benzoic acid less acidic
activating groups
An ester in a five-membered ring is called a?
γ-lactone
An amide in a four-membered ring is called a?
β-lactam
Groups that donate electron density activate a benzene ring towards electrophilic attack and make a benzoic acid ___________
less acidic
Common electron donating groups are?
R groups
groups that have an N or O atom (with a lone pair)
activating groups make a benzoic acid?
less acidic
these contain two carbonyl groups joined by a single oxygen atom
anhydrides
Common electron-withdrawing groups are?
halogens
As the basicity of Z increases, the stability of RCOZ _____________ because of added resonance stabilization.
increases
Groups that withdraw electron density deactivate a benzene ring towards electrophilic attack, and make a benzoic acid?
more acidic
Electron-withdrawing groups stabilize a conjugate base, making a carboxylic acid?
more acidic
_________________________ groups stabilize a conjugate base, making a carboxylic acid more acidic
Electron-withdrawing
___________________ groups destabilize the conjugate base, making a carboxylic acid less acidic
Electron-donating
types of anhydrides
Symmetrical anhydrides
Mixed anhydrides
Cyclic anhydrides
The more electronegative the substituent, the __________ the acid
stronger
these are classified as 1°, 2°, or 3° depending on the number of carbon atoms bonded directly to the nitrogen atom
amides
examples of carboxylic acid derivatives
Acid chlorides
Anhydrides
Esters
Amides
deactivating groups make a benzoic acid?
more acidic
Common electron-withdrawing groups are the?
Halogens
groups with an atom Y
A ______________________ is a stronger acid than an alcohol or phenol because its conjugate base is most effectively resonance stabilized
carboxylic acid
Electron-donating groups destabilize the conjugate base, making a carboxylic acid?
less acidic
The larger the number of electronegative substituents, the __________ the acid
stronger
Groups that withdraw electron density _____________ a benzene ring towards electrophilic attack, and make a benzoic acid more acidic.
deactivate
Common electron-donating groups are?
alkyl groups
The closer the electron-withdrawing group to the COOH, the ____________ the acid.
stronger
Polarizable ________________ donate electron density, and thus exhibit an electron-donating inductive effect
alkyl groups
these have two identical alkyl groups bonded to the carbonyl carbons
symmetrical anhydrides
An amide in a four-membered ring is called a β-lactam, because the β carbon to the carbonyl is bonded to the?
heteroatom
these have two different alkyl groups
mixed anhydrides
these are called lactams
amides
alkyl groups are _________________, making them electron-donating groups
polarizable
these groups make a benzoic acid more acidic
deactivating groups
Substituents on a benzene ring either donate or withdraw an?
electron density
Groups that withdraw electron density deactivate a benzene ring towards _______________ attack, and make a benzoic acid more acidic
electrophilic
Groups that donate electron density activate a benzene ring towards ______________ attack and make a benzoic acid less acidic
electrophilic
