Ch. 17-18 info Flashcards
Values of pKa for aliphatic carboxylic acids are in the range
4-5
Treating a Grignard reagent with carbon dioxide (CO2) gives the magnesium salt of a carboxylic acid, which, upon protonation with aqueous acid, gives a
carboxylic acid
besides lialh4, other reducing agents such as catalytic hydrogenation and NaBH4 cannot reduce a …, so these can be used to reduce other functional groups without affecting a ….group in the same molecule.
carboxylic acid; carboxyl
…is used to form methyl esters from carboxylic acids. The mechanism involves protonation of the …by the carboxylic acid to make a methyldiazonium cation, followed by attack of the resulting carboxylate on the methyldiazonium cation to give the ….
diazomethane; diazomethane carbon atom; methyl ester and N2.
Carboxylic acids with a carbonyl b to the carboxyl group undergo … upon heating
decarboxylation (loss of CO2)
b-Ketoacids decarboxylate upon heating. The mechanism involves redistribution of electrons in a six- membered transition state to give CO2 and the enol of a ketone, which tautomerizes to give a …. The reaction is facilitated by a hydrogen bond between the carboxyl hydrogen atom and b-carbonyl oxygen.
ketone
(common names) methanoic acid
formic acid
(common names) ethanoic acid
acetic acid
(common names) propanoic acid
propionic acid
(common names) butanoic acid
butyric acid
(common names) pentanoic acid
valeric acid
(common names) hexanoic acid
caproic acid
The name of the anion is derived from the name of the carboxylic acid by dropping the suffix -ic acid and adding the suffix…
-ate
The carboxyl group is one of the organic functional groups most resistant to …
reduction
an acyl group is
R-C=O
acid halides are named by replacing the ic acid of the parent acid with …
-yl halide
acid anhydrides are named by replacing the word acid of the parent acid with …
anhydride
the alkyl or aryl group bonded to the O atom is named .., followed by the name of the parent acid in which -ic acid is replaced by …
-ate
lactones are … in which the acyl C and O atom are part of the ring
cyclic esters
if the n atom of an amide has one or two groups attached, the groups are named after the designator …; then -ic acid of the parent acid is replaced by …
N-; -amide
lactams are … in which the acyl C and N atom are part of the ring
cyclic amides
the amide acyl C atom is less … than that of the other carboxylic acid derivatives
electrophilic
the amide N atom is not …
basic
nitriles are named by replacing -oic acid of the parent acid with …
-onitrile
imides have two … groups attached to the same N atom
acyl groups
imides are considerably more acidic than … due to …. of the negative charge of the N-deprotonation anion over both carbonyls
amides; delocalization
