carboxylic amines and amides

7/25/2019 Carboxylic Amines and Amides

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O



Sulfur analogs of esters

• Thioesters, like esters, have relatively low boilingpoints (compared to alcohols and carboxylicacids) and may be found in foods as avorings

• !cetyl coen"yme !, a thioester, is important inmetabolic cycles that provide our bodies withenergy

#ethyl thiobutanoate



!cid chlorides and acidanhydrides• !cid chlorides and anhydrides have structures

that are $uite similar to carboxylic acids andesters

• %oth are able to be hydroli"ed to produce

carbolxylic acids

• !cid chlorides are produced by reaction of acarboxylic acid with an inorganic chloride (&'l,

&'l, or SO'l*)



!cid chlorides and acidanhydrides

•

!cid chlorides are named as follows+ – rst as a carboxylic acid

– -emove the ./ic acid0 and add ./oyl chloride0

1ydrolysis reaction+

2sterication+




• !cid anhydrides are made by condensationreactions between carboxylic acids (or betweenacid chlorides and carboxylic acids)+

• 3aming is straightforward+ indicate the names ofthe acids used to make the anhydride (withoutthe .acid0 part included)




• 'arboxylic acids (esters, acid chlorides4) possess an acylgroup (notice how this is di5erent that the carboxyl group ofthe acid)

• !cyl transfer reactions occur during protein synthesis Thereaction involves the formation of a new bond between theacyl group and another molecular fragment

•

One example of an acyl transfer occurs during anesterication+

!cyl transfer reactions

!cyl group



2sters and anhydrides of inorganicacids

• 6norganic acids like 1*SO7, 1&O7, and 13O can

also react with alcohols to make inorganic esters+




• &hosphate esters are the most important class ofinorganic esters

• %ecause phosphoric acid has three O1 groups, itcan form mono/, di/ and tri/esters+




• &hosphoric acid anhydrides are also made viacondensation reactions+

• These systems are important components of cellularprocesses for biochemical energy production

carboxylic amines and amides

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