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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
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!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*)
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!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+
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!cid chlorides and acidanhydrides
• !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)
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!cid chlorides and acidanhydrides
• '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
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2sters and anhydrides of inorganicacids
• 6norganic acids like 1*SO7, 1&O7, and 13O can
also react with alcohols to make inorganic esters+
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2sters and anhydrides of inorganicacids
• &hosphate esters are the most important class ofinorganic esters
• %ecause phosphoric acid has three O1 groups, itcan form mono/, di/ and tri/esters+
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2sters and anhydrides of inorganicacids
• &hosphoric acid anhydrides are also made viacondensation reactions+
• These systems are important components of cellularprocesses for biochemical energy production
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