Organic Chemistry- Carboxylic Acid Derivatives Flashcards
Carboxylic acids derivatives replace what, on the carboxyl group with what?
The -OH on the carboxyl group with another leaving group (-HR2, -OR, and -OCOR)
Do the carboxylic acid derivatives react similarly to carboxylic acids?
Yes
What are the carboxylic acid derivatives?
Amides
Esters
Anhydrides
How are the carboxylic acids derivatives formed?
By condensation reaction iwth a carboxylic acid
What is condensation?
A reaction that combines two molecules into one, while losing a small molecule.
During the condensation of carboxylic acid, what small molecule is lost?
Water
How is the water molecule formed during the condensation of the carboxylic acid?
From the hydroxyl group of the carboxylic acid and a hydrogen associated with the incoming nucleophile.
What should you focus on when dealing with derivatives of carboxylic acid?
The relevant nucleophile that forms the derivative and the nomenclature of the functional group.
What are amides?
Compounds with the general formula RCONR2
How are amides named?
They are named by replacing the -oic acid suffic with -amide. Alkyl substituents on the nitrogen atom are listed as prefixes, and their location is specified with the letter N-
What are examples of Amides?
N-ethyl-N-methylbutanamide
N, N-dimethylethanamide
N-methylpropanamide
How are amides synthesized?
By the reaction of other carboxylic acid derivatives with either ammonia or an amine
Why will only primary and secondary amides undergo a reaction?
The loss of hydrogen from the nucleophile required for this reaction to take place
cyclic amides are called what?
Lactams
How are lactams named?
They are named according to the carbon atom bonded to the nitrogen.
Beta-lactams contain a bond between what?
The beta-carbon and the nitrogen
y-lactams contain a bond between what?
The y-carbon and the nitrogen
What are 4 examples of lactams?
Beta-lactam
y-lactam
Delta-lactam
Sigma-lactam
Why or why not do amides participate in hydrogen bonding?
Depending on the number of alkyl groups they have bonded
What are the boiling points of amides dependent on?
They’re hydrogen bonding makes their boiling poits lower or on the same level as the boiling points of carboxylic acids.
What are esters?
The dehydration synthesis products of other carboxylic acid derivatives and alcohols
How are esters named?
By placing the esterfying group (The substituent bonded to the oxygen) as a prefix; the suffix -oate replaces -oic acid
How is ethyl acetate formed?
From the condensation of acetic acid and ethanol
What is ethyl acetate called in IUPAC?
Ethyl ethanoate
What are examples of esters?
Ethyl ethanoate
Isopropyl Butanoate
What is Fischer esterification?
Under acidic conditions, mixtures of carboxylic acids and alcohols will condense into esters
How can esters also be obtained?
From the reaction of anhydrides with alcohols.
Cyclic esters are called what?
Lactones
How are lactones named?
In the same manner as lactams with the name of the precursor acid molecules also included.
Why do esters usually have lower boiling points then carboxylic acids?
Because they lack hydrogen bonding
What are triacylglycerols?
The storage form of fats in the body, are esters of long-chain carboxylic acids (fatty acids0 and glycerol (1,2,3-propanetriol)
What is sponification?
The process by which fats are hydrolyzed under basic conditions to produce soap
What regenerates the fatty acids from soap?
Subsequent acidification of the soap
What’s another name for anhydrides?
Acid anhydrides
What are anhydrides?
the condensation dimers of carboxylic acids. These molecuels have the general formula (RC(O)OC(O)R)
How are symmetrical anhydrides named?
By subtituting the word anhydride for the word acid in a carboxylic acid.
How are asymmetrical anhydrides named?
Name the two chains alphabetically followed by anhydride
What are two examples of cyclic anhydrides?
Phthalic and succinic anhydrides
How are cyclic anhydrides derived?
Arising from intramolecular condesnation or dehydration of diacids
What are examples of anhydrides?
Ethanoic propanoic anhydride
Ehanoic anhydride (acetic anhydride)
Phthalic anhydride
Succinic anhydride