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Name 3 Carboxylic Acid Derivative reactions that involve nucleophilic substition.
1. Hydrolysis
2. Ester conversion
3. Amide conversion
Acid halide + H2O =
RCOOH (carboxylic acid)
Acid Halide + ROH =
RCOOR (ester)
Acyl Halides + NH3 =
Amides
Friedel Crafts Acylation takes place via nucelophilic/electrophilic substition on an aromatic ring.
Electrophilic aromatic substitution
Acid halides can be reduced to alcohols or selectively reduced to intermediate aldehydes via
H2/Pd/BaSO4 Quinoline
The most common and important anhydride that is a dimer of acetic acid is
Acetic anhydride
Anhydrides are formed via
2 acid molecules condensing(losing water)
Name 3 ways in which anhydrides can be made:
1. RCOOH + RCOOH
2. Acid chloride + carboxylate salt
3. Heating
Certain cyclic anhydrides can be formed simply by heating carboxylic acids. This reaction is driven by...
the increased stability fo the newly formed ring hence only 5 or 6 membered rings are EASILY formed
Anhydride + H20 =
RCOOH
Anhydride + NH3 =
Amide + ammonium carboxylate
Anhydride + ROH =
RCOOR + RCOOH (Ester + Carboxylic acid)
Amides can be hydroylzed under acidic conditions to produce...

RCON + H20 =
Carboxylic acids which occurs via nucleophilic substitution
What is the Hoffman Rearrangement?
Conversion of amides to 1'amines through the loss of a carbonyl carbon
The nitrogen equivalent of a carbene called a ______________ is a step in a ______________.
Nitrene/Hoffman Rearrangement where a amides are converted to 1'amines.
Amides are reduced with LAH to yield
amines
Acid + alcohol =
Ester. Esters are the dehydration products of RCOOH and ROH.
According to the IUPAC system esters are named as...
alkyl or aryl alkanoates.
What are triacylglycerols?
Esters of long chain carboxylic acids and glycerol. AKA fats
What is saponification?
The process where fats are hydrolyzed to produce soap.
Saponification takes place under acidic/basic conditions.
Basic
What is transesterification?
When a different alcohol attacks an ester.
Grignard + Ester =
Ketone
What is Claisen condensation and what is it also known as?
The process whereby the enolate ion of one ester acts as a nucleophile, attacking another ester.
AKA acetoacetic ester condensation.
Esters may be reduced to 1' alcohols with what?
a. LAH
b. NaBH4
c. KMnO4
LAH, but not with NaBH4. this allows for selective reduction of molecules with multiple functional groups.
RCOOH + SOCl2, PCl3, PCl5 or PBr3 =
acyl halide
These participate in Friedel-Crafts acylation to form an alkyl aryl ketone.
Acyl halides
Esters + 2 Grignard =
3'ROH
During the hydrolysis of an acid chloride, pyridine (a base) is usually added to the reaction vessel b/c
it acts as a base and serves to neutralize the HCl that has formed.
In order to produce a 1'amide, an acid chlorid should be treated with
a. ammonia
b. an alcohol
c. 1'amine
d. 3'amine
a. ammonia
Acid chlorides react with ammonia to form amides. Since the amine is replacing the OH group there must be at least one hydrogen on the amine. A 1' amine reacting with an acid chloride would give a compound in which the N is substituted.
What is the best method of producing methyl propanoate?
a. Propanoic acid + methanol in the presence of a mineral acid
b. Ethanol + propanoyl chloride in the presence of a base
c. propanoyl chloride with an aqueous base
d. propanoic acid + ethanol in the presence of a mineral acid
A. Methyl propanoate is an ester, it can be synthesized by reacting a RCOOH + ROH in the presence of an acid