Chem ch 17 Flashcards
Carboxylic acid (cooh the box)
A compound that has a carbonyl group bonded to an –OH group, RCOOH
Acid anhydrides (anything formed when H20 is removed) are formed when…(ana is 2)
two carboxylic acids join together by eliminating a molecule of water.
carboxylic acids, esters, and amides all have…
polar and structural similarities
carboxylic acids, esters, and amides all…(bp) AND which can H bond…
All boil at a higher temperature than comparable alkanes, and carboxylic acids and amides that have an H on the nitrogen can hydrogen bond
carbonyl-group substitution reactions
—Z replaces (substitutes for) the group bonded to the carbonyl carbon atom
carbonyl-group substitution reactions are quite often called…(sub in the ace)
acyl transfer reactions.
carboxylic acids can or can’t form hydrogen bonds with each other?
they can
Carboxylic Acids - which ones are soluble? (soluble box has 4 sides)
those with up to four carbons are water-soluble
Acids with saturated, straight-chain R groups of up to nine carbon atoms are…(9 acidic drinks)
volatile liquids with strong, pungent, and usually unpleasant odors
Carboxylic acids naming
replace the final -e of the corresponding alkane name with -oic acid
carboxylic acids - common names
the carbon atoms attached to the –COOH group are identified by Greek letters α, β, γ and so on, rather than numbers
The acyl group that remains when a carboxylic acid loses its –OH is named by replacing the…(acyl gargoyl)
-ic at the end of the acid name with -oyl
Dicarboxylic acids
contain two –COOH groups, are named systematically by adding the ending -dioic acid to the alkane name (the -e is retained).
Unsaturated acids (double bonds) are named systematically in the IUPAC system with the ending in…(this is just alkene - pass)
-enoic, ex. H2C=CHCOOH, is named propenoic acid.
when writing common name for carboxylic acid, REMEMBER…(y-ric is commonly known)
it will end in yric - ex. β-hydroxy-α-methylbutyric acid
When the –OH of the carboxyl group is converted to the –OR of an ester group…(hydrogen bonding…)
the ability of the molecules to hydrogen bond with each other is lost
esters properties (esters liquids are boring but smell good)
Simple esters are colorless, volatile liquids with pleasant odors, and many of them contribute to the natural fragrance of flowers and ripe fruits.
esters - high or low bp?
low bp
ester naming
The first is the name of the alkyl group R’ in the ester group. The second is the name of the parent acid, with the family-name ending -ic acid replaced by -ate.
amides w/ NH2 attached can or can’t form H bonds?
they can form H bonds
unsubstituted amides are..(solubility)
are soluble in both water (with which they form hydrogen bonds) and organic solvents
Monosubstituted amides (RCONHR’) can…(h bonds)
form hydrogen bonds to each other
disubstituted amides (RCONR2’)…
cannot form H bonds and are, therefore, lower boiling.
difference btwn amide and amine
amide the NH is bonded directly to carbonyl group, amine it’s not
amide naming
unsubstituted –NH2 group are named by replacing the -ic acid or -oic acid of the corresponding carboxylic acid name with -amide
Carboxylate anion
Carboxylate anion: The anion that results from the ionization of a carboxylic acid, RCOO–
Carboxylate anion naming (I ate the COO)
Carboxylate anions are named by replacing the -ic ending in the carboxylic acid name with -ate.
The comparative strength of an acid is measured by…
its acid dissociation constant (Ka); the smaller the value of Ka, the weaker the acid.
pKa (–log Ka) (Ka likes acid)
is often used when discussing the acidity of organic and biomolecules
With pKa, the…(opposite of K)
larger and more positive number, the weaker the acid is
There is a 10-fold difference in…
acidity for every 1 pKa unit.
Carboxylic acids undergo neutralization reactions…
to give water and a carboxylic acid salt, as shown here for the formation of sodium acetate
ester and amide formation
The reactions of alcohols and amines with carboxylic acids follow the same pattern—both result in substitution of other groups for the –OH of the acid and formation of water.
in ester and amide formation..
you literally just move things around to form + H2O
Esterification is…(AND what is the catalyst) (esterification is warm)
carried out by warming a carboxylic acid with an alcohol in the presence of a strong-acid catalyst, such as sulfuric acid - just switching the last part to form + H20
Amide Formation (amide drinking ammonia?)
Unsubstituted amides are formed by the reaction of carboxylic acids with ammonia
Substituted amides are…
produced in reactions between primary or secondary amines and carboxylic acids
amide formation steps
The first step of the reaction is formation of the ammonium salt; amide formation reactions must be heated to proceed.
The overall reaction is formation of an amide accompanied by formation of water.
amide formation - Tertiary amines…
do not have a hydrogen on the amine nitrogen and, therefore, do not form amides, generating only the ammonium salt.
Esters and amides undergo hydrolysis to…
Esters and amides undergo hydrolysis to give back carboxylic acids plus alcohols or amines
hydrolysis does what to esters and amides?
turns them back into carboxylic acids
Acid-catalyzed hydrolysis is simply the reverse of…
the esterification
Both acids and bases can cause…
ester hydrolysis
saponification (basic ester is such a sap)
Ester hydrolysis using a base such as NaOH or KOH
Amides are stable in water, but…
hydrolyze with heating in the presence of acids or bases
Nylons are…
Nylons are polyamides produced by reaction of diamines with diacids
Diacids and dialcohols react to yield…
polyesters
Phosphate ester
A compound formed by reaction of an alcohol with phosphoric acid
Phosphoric acid description (phos is like box)
Phosphoric acid is an inorganic acid with a striking resemblance to a carboxylic acid; it has three acidic hydrogen atoms, allowing it to form three different anions
phosphoric acid reacts with…
alcohols to form phosphate esters. It may be esterified at one, two, or all three of its –OH groups by reaction with an alcohol
Phosphate monoesters and diesters are acidic or basic? (die acid)
they are acidic because they contain acidic hydrogen atoms. In neutral or alkaline solutions, they are ions.
phosphoryl group
The PO32− group as part of a larger molecule
Two or three molecules of phosphoric acid can combine to lose water and form…
diphosphoric and triphosphoric acid. These anhydride-containing acids can also form esters, which are known as diphosphates and triphosphates
phosphorylation
the transfer of a phosphoryl group from one molecule to another
In biochemical reactions, phosphoryl groups are often provided by a triphosphate (adenosine triphosphate, ATP)
which is converted to a diphosphate (adenosine diphosphate, ADP) in a reaction accompanied by the release of energy
The addition and removal of phosphoryl groups is a common mechanism for regulating…
the activity of biomolecules
Organic phosphates contains what linkages? (Phos is the boss)
C-O-P linkages
Organic phosphates with one or two R groups (properties)
(monoesters or diesters) are acids and exist in ionized form in body fluids
diphosphate and triphosphate groups
important in biomolecules, contain one or two phosphoanhydride linkages, respectively
Phosphorylation
the transfer of a phosphoryl group from one molecule to another
ending for carboxylic acids (the box is stoic)
oic acid
alanine (alana eats aminos in 3s)
alpha aminopropionic acid
when the OH group from the carboxylic acid is taken off, the naming is…(oh removes oil)
ends oyl. ex - propanoyl
naming if there is 2 COOH groups
dioic acid
unsaturated acids (carboxylic acids w/ more than one C double bond) naming (not quite oic)
end in enoic
common naming for carboxylic acids
will be alpha, beta, etc. and don’t forget to change last part to yric acid. ex. a-methylbutyric acid
esters are just…
carboxylic acids with the OH replaced by OR.
naming esters (ester ate the left parent)
the O and everything to the right is the alkyl - ie - ethyl, and the double bond and C and everything to the left is parent ending in ic or ate. ie ethyl acetate.
as long as there is an NH (doesn’t have to be NH2) it’s an..
amide
N attached directly to carbonyl group is an…(it can be an N or NH2)
amide
acetic acid - describe
2 Cs (one part of the carboxyl group) and an OH. Just a carboxyl with an extra CH3 attached
difference btwn amides and amines
in amide the N is bonded directly to the carbonyl group, but not in amines
amides naming - they literally just end in…
amide
RCOO- (name)
carboxylate anions
carboxylate anions naming
ic is replaced with ate
the smaller Ka, the ____the acid
weaker
esterification
warming carboxylic acid with alcohol
primary amides are formed by the reaction of…
carboxylic acid and ammonia (NH3)
secondary and tertiary amides are produced…
during reactions between primary and secondary amines and carboxylic acids
ester (sings ohio)
O=C-O
