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80 Cards in this Set

  • Front
  • Back
What is a carboxyl group?
A carbonyl attached to a hydroxyl group
Acetic acid is derived from __ via fermentation
ethanol
acid or base
what are CA's?
acid
When a CA does give away a proton, the leftover electrons are resonated b/w ___ atoms
two oxygen
CA has a hydrogen bond ___ and ___ in the same functional group, leading to ____ intermolecular forces and ___ B.P.'s
donor, acceptor, large, high
The carbonyl carbon is ____
electropositive
*so it makes it a great electrophile
CA's have the ___ priority in nomenclature
highest
t or f
CA's occur widely in nature and are synthesized by all living organisims
t
CA's are always named by adding the suffix...
-oic acid
What are the common and IUPAC names of the first 3 carboxylic acids?
methanoic acid => formic acid
ethanoic acid => acetic acid
propanoic acid => propionic acid
Cyclic carboxylic acis are usually names as what?
cycloalkane CA's
Salts of CA's are named beginning with the ___, followed by the ____.
cation, name of the acid with the ending -ate

Ex) Sodium hexanoate
What is a dicarboxylic acid?
Molecules with two carboxyl groups on the same molecule
What are the first 6 straight chain terminal dicarboxylic acids?
oxalic
malonic
succinic
glutaric
adipic
pimelic
polar or non polar
What are CA's?
polar
Can CA's form hydrogen bonds with each other?
yes
As a result of hydrogen bonding CA's can form what?
dimers
Define dimers?
pairs of molecules connected by two hydrogen bonds
Multiple hydrogen bonds ___ the boiling and melting point of CA's
elevate
BP ___ with increasing MW
increase
CA's acidity is due to what?
resonance stabilization of the carboxylate anion
What happens when the hydroxyl proton dissociates from the acid?
The negative charge left on the carboxylate group is delocalized b/w the two oxygen atoms
Name 2 ways to stabilize the negative charge to increase acidity:
1. electron withdrawing groups (halides)
2. groups that allow more resonance stabilization (benzyl or allyl)
How does electron withdrawing groups influence acidity?
Absorbs the negative charge and increases acidity
How does electron donating groups influence acidity?
Donates additional electron density and destabilizes the negative charge, making the compound less acidic
In dicarboxylic acids, one -COOH group influences the other, making the compound what?
more acidic
Beta-dicarboxylic acids are notable for what?
high acidity of the alpha-hydrogens located on the carbon b/w the two carboxyl groups
CA's are the most ___.
oxidized
CA's can be prepared via oxidation of...
aldehydes, primary alcohols, and certain alkylbenzenes
What oxidant is normally used to oxidize CA's?
KMnO4
Why can't secondary and tertiary alcohols be oxidized to carboxylic acids?
B/c of valence limitations
Organometallic reagents react with ___ to form ___.
CO2, CA's
Give an example of an organometallic reagent
Grignard reagents
Carboxylation of organometallic reagents is useful for the conversion of ___ alkyl halides into CA's
tertiary
Carboxylation of organometallic reagents adds ___ carbon atom to the chain
one
Nitriles are also called what?
cyanides
HYDROLYSIS OF NITRILES
The cyanide anion carries the ___ charge on the ___ atom, making it a great ___, but not a great ___.
negative, carbon, nucleophile, base
HYDROLYSIS OF NITRILES
The cyanide anion will displace __ and ___ halides in a typical SN2 fasion
primary and
HYDROLYSIS OF NITRILES
Nitriles can be hydrolyzed under either __ or __ conditions
acidic, basic
HYDROLYSIS OF NITRILES
This reaction allows for the conversion of ___ into ___.
alkyl halides, CA's
HYDROLYSIS OF NITRILES
As in the carboxylation reaction, an additional __ is introduced into the chain
carbon
What do long chain carboxylic acids form when they react with sodium or potassium hydroxide?
salt
How do you make soap?
by mixing fat (triglycerides) with lye (sodium hydroxide)
Why can salts solvate nonpolar organic compounds in aqueous solutions?
They possess both a nonpolar tail and polar carboxylate head
Define micelles
soap molecules that arrange themselves in spherical structures
SOAP FORMATION
The ___ face outward, where they can be solubilized by water, the ___ are oriented inward where it is protected
polar heads, nonpolar hydrocarbon chains
Many of the reactions in which CA's participate proceed via a single mechanism called what?
nucleophilic acyl substitution
Nucleophilic acyl substitution is similary to...
nucleophilic addition to a carbonyl
Carboxylic acids and esters can only be reduced by __ and not the less reactive ___.
LiAlH4, NaBH4
most or least
CA's occupy the ___ oxidized end of the oxidation-reduction continuum
most
yes or no
Can CA's be further oxidized?
no
LAH reduces CA's to ___.
alcohols
Show reduction of a CA mechanism
carboxylic acid => aldehyde => alcohol
Reduction of a CA occurs by nucleophilic ____ of ____ to the carbonyl group
addition, hydride
How do you synthesize esters?
react CA's with alcohols under acidic conditions
Ester formation is a ____ reaction, so ___ is a side product.
condensation, water
ESTER FORMATION
In acidic conditions, the ___ on the C=O can be protonated. This enchances the ___ of the bond, putting more ___ charge on the C, and making it ___ susceptible to nucleophilic attack
O, polarity, positive
ESTER FORMATION
This condensation reaction occurs most rapidly with ___ alcohols
primary
Whats another name for acyl halides?
acid halides
What are acyl halides?
Compounds with carbonyl groups bonded to halides
How is thionyl chloride written?
SOCl2
What does thionyl chloride do?
A reagent that can convert CA's into acyl halides
reactive or nonreactive
Acid cholorides.
reactive
Acid chlorides are frequently used as ____ in the conversion of CA's to ___ and ___.
intermediates, esters and amides
What biochemical pathway is decarboxylation most common in?
Krebs Cycle
What is decarboxylation?
loss of a carbon
Whenever we want to get rid of a carbon on the MCAT, it will be lost in the form of ___?
CO2
t or f
Acid chlorides are most stable and least reactive
f
Acid chlorides are the least stable and the most reactive
____ and other ____ may spontaneously decarboxylate when heated.
1,3 Dicarboxylic acids and other beta-keto acids
DECARBOXYLATION
the carboxyl group is lost and replaced with what?
hydrogen
DECARBOXYLATION
Because both the electrophile and nucleophile are in the same molecule, the reaction proceeds....
through a six membered ring transition state
DECARBOXYLATION
The ___ that is initially formed from the destruction of the ring tautomerizes to the more stable __ form.
enol, keto
The more stable the ___ is, the more likely it is that the ___ will leave
conjugate base, proton
CA stability is determined by what 3 factors?
-periodic trends (electronegativity, and thus, induction)
-size of the anion (HF is a weaker acid than HI)
-resonance
The acidity of a CA is enhanced by...
resonance b/w its oxygen atoms
Primary alcohols or aldehydes can be ___ by CA's
oxidized
What 2 ways can CA's be synthesized?
-from the carbocation of organometalic reagents
-by hydrolyzing nitriles
Carboxylic acids can be reduced to primary alcohols or stopped at the aldehyde level with a...
bulky hydride reagent
CA's with long chains form soaps when neutralized with ___ or ___.
NaOH or KOH
1,3 Dicarboxylic acids and other beta-keto acids may spontaneously decarboxylate when heated producting...
a ketone and carbon dioxide