Ch 20: Carboxylic acids and they are derivatives: NAS Rxn Flashcards
Compounds with parallel properties to carboxylic acids…
R-C triple bond N:
The week base who’s conjugate acid has the highest PKA is the ___________. 
Strongest
How do you name acyclic acid chlorides by IUPAC?
- acid chlorides come from carboxylic acids
-end in -oyl chloride
Ex:ethanoyl chloride
How do you name acid chloride that are in a ring compound by IUPAC? 
Cycloalkane name + carbonyl chloride
How do you commonly name acid chlorides?
Prefix + -yl chloride
Acid anhydrates derive from…..
Two carboxylic acids
How do you name Symmetrical acid anhydrides?
Prefix + -ic anhydride
How do you name mix anhydrides?
-two Prefixes + anhydride (alphabetically) 
Esters are made of an _____ and an _____ group.
Acyl, alkyl
What is the IUPAC and common naming for esters?
IUPAC—— -oate
Common —— -ate
How do you name special ring compounds that include Esther‘s?
Name R’ + name of cycloalkane ring + carboxylate
How do you name primary acyclic Amides by IUPAC?
- amide
-  names end in amide or Carboxamide 
How do you name cyclic primary amides by IUPAC?
Cycloalkane name + carboxamide
how do you name amides by the common name?
Prefix + -amide
How do you name secondary and tertiary amides by the common name? 
N- prefix before each R’ group
How do you name nitriles by IUPAC?
Name ends in -nitrile
-named as alkanenitriles
How do you name nitriles by their common name?
-onitrile
-CN as a substituent is an ________ group 
Cyano
Esters and amides have a higher priority than… 
Nitriles, alcohols, ketones
Primary and secondary amides have ______ bonds Between their molecules
Hydrogen
L what kind of intermolecular forces do acid chlorides, esters, amides, acid anhydrides, and nitriles have?
Dipole dipole interactions and van der Waals forces
Primary and secondary amides have hydrogen bonding as well 
- have higher BP and MP of comparable nonpolar substances of similar molar mass, primary and secondary amides even higher. 
Conjugated carbonyl groups absorb at ________ Frequencies
Lower
As carbonyl ring size decreases, carbonyl groups absorb at _________ frequencies
Higher
Peptides, polypeptide, proteins are _____ 
Amides
What is used to synthesize aspirin?
Acetic anhydride
What is a carboxylate?
Conjugate base of carboxylic acid
Since Cl is The best leaving group among these compounds, ____________ Are difficult to prepare through acyl nucleophilic substitution reaction
Acid chlorides 
What is added to remove the HCl formed with an acid chloride reaction?
Pyridine (neutralizes) 
Reactions with acid chloride and carboxylate ions produce
Acid anhydride
Reaction with acid chloride and water produces….
A carboxylic acid
Acid anhydrides are _______ reactive than acid chloride
Less
Reaction of acid anhydride With water produces….
Two carboxylic acids
Reaction with acid anhydride with alcohols produce…
An Ester and a carboxylic acid
Acid-base reactions are _______ Than nucleophilic ones
Faster
What is required in the conversion of dicarboxylic acids to cyclic anhydrides? 
High Heat
What reagent is used in Fisher esterfication? 
Carboxylic acid to an ester
H2SO4
What reagent is used for intramolecular cyclization of Gamma and Delta hydroxy carboxylic acids? 
H2SO4
Produces gamma-lactone and H2O
What is DCC?
A drying agent
What reagent is used to convert carboxylic acids to primary amides? 
- NH3
2. heat
Esters undergo what three types of reactions?
- hydrolysis in acid
- hydrolysis in base
- Reactions with amines
What reagent is used for ester hydrolysis in acid?
What does it produce?
H2SO4
 carboxylic acid and alcohol
Because it is reversible, a large excess of water is used to drive the reaction to the right
What reagent is used for Ester hydrosis in base?
What does it produce?
OH-
H2O
Carboxylate ion and an alcohol
Carboxylate ion can be converted to a carboxylic acid with a.….
Strong acid
-NH2 is a poor leaving group therefore, ________ Are least reactive OK sometimes covered in the unit. However, they do hydrolyze under strenuous conditions in acid or base
Amides
What reagent is used for hydrolysis of amides in acid?
What is produce?
H2O
H+
Carboxylic acid and an ammonium ion
What is produced in hydrolysis of amides in base?
What is the reagent?
A carboxylate ion and an amine
H2O
OH-
The lack of reactivity of ________ amides make Proteins very stable in the body
Amides
Nitros do not have leaving groups therefore they do not undergo what type of reactions? What reacting do they go?
Nucleophilic substitution reaction
Nucleophilic addition reactions at the electrophilic carbon
What reagent is needed for the reduction of nitriles?
Strong reducing agent
- LiAlH4
- H2O
Reduces to an amine?
Reduction of nitriles with
1.DIBAL-H
2.H20
Produces an….
Aldehyde
What reagent is used to produce a ketone from nitriles?
- R’M
2. H2O
