Chapter #8 Flashcards
(43 cards)
are carboxylic acids or alcohols more acidic?
carboxylic acids: they have more resonance (two oxygen atoms) that stabilizes the negative charge when the Hydrogen leaves.
for the basic common named carboxylic acids, how many carbons do formic acid, acetic acid, and propionic acid have respectively?
1
2
3
how many carbons does formaldehyde have?
1
how are cyclic carboxylic acids named?
name the cycloalkane and then add carboxylic acid as the suffix
how are salts of carboxylic acids named?
beginning with the cation followed by the name of the acid with -oate ending instead of -oic ending.
how do you name a molecule with 2 carboxylic acid groups?
“-dioc acid” at the end of the alkane name.
Ex: butanedioc acid
what is the name of the structure with: 2 carboxylic acid groups and 2 carbons total
ethanedioic acid
oxalic acid
what is the name of the structure with: 2 carboxylic acid groups and 3 carbons total
propanedioic acid
malonic acid
what is the name of the structure with: 2 carboxylic acid groups and 4 carbons total
butanedioic acid
succinic acid
do alcohols or carboxylic acids have a higher boiling point and why?
carboxylic acids because they have a greater ability to H-bond (with the O-H group and the carbonyl O)
compare acidity of alcohols and carboxylic acids
A carboxylic acid is, therefore, a much stronger acid than the corresponding alcohol, because, when it loses its proton, a more stable ion results
compare the acidity of carboxylic acids and strong acids such as HCl
strong acids are stronger (pKa can be in the negatives while the pKa of carboxylic acids is around 4)
how can acidity be increased via substituents
more electron withdrawing groups increase acidity
is NO2 an electron withdrawing or donating group
electron withdrawing
is NH2 an electron withdrawing or donating group
electron donating
in terms of stabilization or destabilization, the _____ the substituent groups are to the carboxyl group, the ____ the effect.
closer
greater
compare the removal of carboxylic acid protons in monocarboxylic acids and dicarboxylic acids
first in dicarboxylic acid removed easier than mono but the second of dicarboxylic acid is harder to remove than mono
carboxylic acid on other side originally an electron withdrawing group but when the hydrogen leaves and leaves a negative charge then the ability for the other hydrogen to leave diminishes a lot
what is the most acidic hydrogen on a carboxylic acid
the hydroxyl hydrogen
in a beta-carboxylic acid, is the alpha hydrogen more or less acidic than the hydroxyl hydrogens?
less
what type of alcohol can be oxidized to carboxylic acids?
primary alcohols
secondary and tertiary cannot because they already have 2 bonds to carbons.
discuss nucleophilic addition and subtitution
in addition, an OH is formed after addition to carbonyl
in substitution, a leaving group can leave so the carbonyl reforms
____ bases, which are the conjugate bases of strong acids, make good leaving groups
weak (stable)
what conditions are necessary for the formation of an amide from a carboxylic acid and an amine?
basic or acidic
what else is produced in the formation of an amide from a carboxylic acid and an amine?
water molecule