11: Carboxylic Acids and Its Derivatives (Part 1) Flashcards
these are formed from carboxylic acids in many reactions
metal salts of carboxylate anions
these are named by adding the suffix -dioic acid to the name of the parent alkane
diacids
The most important reactive feature of a carboxylic acid is its __________________, which is readily cleaved with base.
polar O – H bond
Carboxylic acids having > 5 C’s are water insoluble because the nonpolar alkyl portion is too large to dissolve in the?
polar H2O solvent
The ___________________ make the carboxy carbon electrophilic, so carboxylic acids react with nucleophiles.
polar C – O bonds
these are weakly basic—they react with strong acids by protonation of the carbonyl oxygen.
carboxylic acids
Carboxylic acids react as _____________________—that is, as proton donors
Brønsted–Lowry acids
____________________ of a carboxylic acid forms a resonance-stabilized conjugate base—a carboxylate anion
deprotonation
Alkyl benzenes having at least one benzylic C – H bond are oxidized with KMnO4 to?
benzoic acid
Carboxylic acids having > 5 C’s are water insoluble because the ________________ is too large to dissolve in the polar H2O solvent.
nonpolar alkyl portion
Deprotonation of a carboxylic acid forms a resonance-stabilized conjugate base—a?
carboxylate anion
carboxylic acids also exhibit _________________________________ because they possess a hydrogen atom bonded to an electronegative oxygen atom
intermolecular hydrogen bonding
With __________________, two carboxylic acids are formed as products
internal alkynes
These ________________ dissolve in a nonpolar fat-like environment but do not dissolve in water
“fatty” acids
__________________ having at least one benzylic C – H bond are oxidized with KMnO4 to benzoic acid
alkyl benzenes
Carboxylic acids having ≤ 5 C’s are water soluble because they can ___________________ with H2O
hydrogen bond
Both ___________ and _____________ alkynes are oxidatively cleaved with ozone to give carboxylic acids
internal, terminal
these have higher boiling points and melting points than other compounds of melting point comparable molecular weight
carboxylic acids
what are the three simplest diacids are most often identified by their common names
oxalic acid
malonic acid
succinic acid
Compounds that have only carbon and hydrogen atoms bonded to the carbonyl group
carbonyl compounds
Carboxylic acids having ________ are water soluble because they can hydrogen bond with H2O
≤ 5 C’s
these are the most polar organic compounds
carboxylic acids
how to prepare carboxylic acids
- by oxidation of 1-degree alcohols
- by oxidation of alkyl benzenes
- by oxidative cleavage of alkynes
these react as Brønsted–Lowry acids—that is, as proton donors
carboxylic acids
insoluble carboxylic acids are called?
fatty acids
Both internal and terminal alkynes are oxidatively cleaved with ozone to give?
carboxylic acids
The polar C – O bonds make the carboxy carbon ________________, so carboxylic acids react with nucleophiles
electrophilic
Compounds that contain an electronegative atom bonded to the carbonyl group
carbonyl compounds
it is always the product regardless of the alkyl benzene used as starting material
benzoic acid
Carboxylic acids exhibit ___________________ interactions because they have polar C – O and O – H bonds
dipole–dipole
There are compounds containing two carboxy groups called?
diacids
_________________ stabilized conjugate base makes an acid stronger
resonance
Both internal and terminal alkynes are ___________________ with ozone to give carboxylic acids
oxidatively cleaved
Alkyl benzenes having at least one benzylic C – H bond are oxidized with ______________ to benzoic acid
KMnO4
these are soluble in organic solvents regardless of size
carboxylic acids
Carboxylic acids having _______ are water insoluble because the nonpolar alkyl portion is too large to dissolve in the polar H2O solvent
> 5 C’s
The polar C – O bonds make the carboxy carbon electrophilic, so carboxylic acids react with nucleophiles, forming?
carboxylate anion
resonance stabilized conjugate base makes an acid?
stronger
With ____________________, the sp hybridized C – H bond is converted to CO2
terminal alkynes
Both internal and terminal alkynes are oxidatively cleaved with ________ to give carboxylic acids
ozone