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Chapter 21 Carboxylic Acid Derivatives (continued)
Organic Chemistry, 6th Edition L. G. Wade, Jr. Chapter 21 Carboxylic Acid Derivatives (continued)
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Hydrolysis of Acid Chlorides and Anhydrides
Hydrolysis occurs quickly, even in moist air with no acid or base catalyst. Reagents must be protected from moisture. => Chapter 21
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Acid Hydrolysis of Esters
Reverse of Fischer esterification. Reaches equilibrium. Use a large excess of water. => Chapter 21
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Saponification Base-catalyzed hydrolysis of ester.
“Saponification” means “soap-making.” Soaps are made by heating NaOH with a fat (triester of glycerol) to produce the sodium salt of a fatty acid - a soap. One example of a soap is sodium stearate, Na+ -OOC(CH2)16CH => Chapter 21
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Hydrolysis of Amides Prolonged heating in 6 M HCl or 40% aqueous NaOH is required. => Chapter 21
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Hydrolysis of Nitriles
Under mild conditions, nitriles hydrolyze to an amide. Heating with aqueous acid or base will hydrolyze a nitrile to an acid. => Chapter 21
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Reduction to Alcohols Lithium aluminum hydride reduces acids, acid chlorides, and esters to primary alcohols. => Chapter 21
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Reduction to Aldehydes
Acid chlorides will react with a weaker reducing agent to yield an aldehyde. => Chapter 21
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Reduction to Amines Lithium aluminum hydride reduces amides and nitriles to amines. Nitriles and 1 amides reduce to 1 amines. A 2 amide reduces to a 2 amine. A 3 amide reduces to a 3 amine. => Chapter 21
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Organometallic Reagents
Grignard reagents and organolithium reagents add twice to acid chlorides and esters to give alcohols after protonation. => Chapter 21
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Grignard Reagents and Nitriles
A Grignard reagent or organolithium reagent attacks the cyano group to yield an imine which is hydrolyzed to a ketone. => Chapter 21
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Acid Chloride Synthesis
Use thionyl chloride, SOCl2, or oxalyl chloride, (COCl)2. Other products are gases. => Chapter 21
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Acid Chloride Reactions (1)
ester amide acid anhydride => Chapter 21
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Acid Chloride Reactions (2)
3° alcohol ketone 1° alcohol aldehyde acylbenzene => Chapter 21 AlCl3
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Lab Synthesis of Anhydrides
React acid chloride with carboxylic acid or carboxylate ion. Heat dicarboxylic acids to form cyclic anhydrides. => Chapter 21
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Anhydride Reactions acid ester amide acylbenzene => AlCl3
Chapter 21
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Anhydride vs. Acid Chloride
Acetic anhydride is cheaper, gives a better yield than acetyl chloride. Use acetic formic anhydride to produce formate esters and formamides. Use cyclic anhydrides to produce a difunctional molecule. => Chapter 21
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Synthesis of Esters acid acid chloride acid anhydride =>
methyl ester => Chapter 21
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Reactions of Esters acid ester amide 1° alcohol 3° alcohol =>
Chapter 21
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Lactones Formation favored for five- and six-membered rings.
For larger rings, remove water to shift equilibrium toward products => Chapter 21
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Polyesters Dacron® thread Mylar® tape Glyptal resin PET bottles =>
Chapter 21
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Synthesis of Amides acid acid chloride acid anhydride ester nitrile
=> Chapter 21
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Reactions of Amides acid and amine amine 1° amine nitrile =>
Chapter 21
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Lactam Formation Five- and six-membered rings can be formed by heating - and -amino acids. Smaller or larger rings do not form readily => Chapter 21
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End of Chapter 21 Chapter 21
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