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Derivatives of carboxylic acids Vladimíra can be oxidized to oxo derivatives (= dehydrogenation) products of esterification (acid + alcohol → ester + water)

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8011_2108_DerivativesofCarboxylicAcids(lectures11and12).pdf

Derivatives of carboxylic acids

Vladimíra Kvasnicová

Derivatives of carboxylic acids

1. substitutional derivatives→substitution in the chain of an acid →no change in the carboxyl group

2. functional derivatives

→functional carboxyl group is changed

Substitutional derivatives

•substitution in the chain of an acid

1.1. HALOGEN DERIVATIVES

R(X)- COOHX = Cl, Br, I, F

•prefix : chloro-, bromo-, iodo-, fluoro-

1.2. HYDROXY DERIVATIVES

R(OH)- COOH

•prefix : hydroxy- • can be oxidized to oxo derivatives (= dehydrogenation) •trivial names! •lactic acid(= 2-hydroxypropanoic acid or a-hydroxypropionic acid) • bbbb-hydroxybutyric acid (= 3-hydroxybutanoic acid) •malic acid(= 2-hydroxybutanedioic acid or a-hydroxysuccinic acid) •citric acid(= 2-hydoxypropane-1,2,3-tricarboxylic acid) •salicylic acid(= 2-hydroxybenzoic acid)

Important hydroxy derivatives

1.3. OXO DERIVATIVES

R- (C ═O)- COOH •prefix: oxo- / keto- • can be reduced to hydroxy derivatives•trivial names!Important oxo derivatives: pyruvic acid(= 2-oxopropanoic acid) acetoacetic acid(= 3-oxobutanoic acid) oxaloacetic acid(= 2-oxobutanedioic acid) aaaa-ketoglutaric acid(= 2-oxopentanedioic acid)

1.4. AMINO DERIVATIVES

R(NH

2)- COOH

•prefix : amino- •a-L-amino acids are found in proteins •trivial names!examples:•glycine(= 2-aminoethanoic acid) •alanine (= 2-aminopropanoic acid) •phenylalanine(= 2-amino-3-phenylpropanoic a.)

Functional derivatives

•functional carboxyl group is changed

2.1. SALTS

R- COO

-M + (M += metal cation) = products of neutralization (acid + base →salt + water) •suffix : -ate or -oate -ic acid →-ate / -oic acid →-oate • R- COO-= carboxylate (anion of c.a.) •full name:cation carboxylate (sodium acetate)

2.2. ESTERS

R1- O-

CO- R 2 = products of esterification (acid + alcohol →ester + water) • the opposite reaction = ester hydrolysis •suffix : -ate •R1- O- = rest of alcohol • R1 = alkyl (from the alcohol name: "alkyl" alkohol) •full name : alkyl carboxylate(methyl acetate = methyl ethanoate)

• ethyl formate = ethyl methanoate• methyl benzoate• methyl salicylate ¹acetylsalicylic acid

• phenyl acetate = phenyl ethanoate • CH 3-CH 2-CH

2-CO-O-CH

3(apple)

• CH 3-CH 2-CH

2-CO-O-(CH

2)4-CH

3(apricot)

• CH

3-CO-O-(CH

2)4-CH

3(banana)

• CH 3-CH 2-CH

2-CO-O-CH

2-CH

3(pineapple)

• H-CO-O-CH 2-CH

3(rum)

Examples of esters

• lower boiling points than carboxylic acids and alcohols (~ absence of hydrogen bonds) • less soluble in water than carboxylic acids• esters have a fruity smell•reactions : ester hydrolysis saponification = hydrolysis by a strong base →salt and alcohol →salts of long chain fatty acids are SOAPS polymerization →polyesters (from difunctional monomers)

Properties and reactions of esters

2.3. ANHYDRIDESR

1- CO- O- CO

- R 2 •acid → anhydride (acetic acid → acetic anhydride ) •organic, organic-inorganic examples• acetic formic anhydride• phtalic anhydride• "phosphoglycerate" (= phosphoric glyceric anhydride)

2.4. AMIDES

R-

CO- NH

2 •suffix : -amide (ethanamide) •-ic or -oic acid →-amide (acetamide ) • substituted -NH

2group:

N-alkyl...amide

•substituted amide groups are found in proteins (the peptide bond = "amide bond")• nitrogen atom contains an unshared pair of electrons → delocalization ⇒ amides are not basic • strong intermolecular H-bonds: amides are solids

• low MW amides are soluble in water• carboxylic acid + ammonia (or amine) →amide + water

2.5. ACYLHALIDES

R- CO- X

X = halogen

•acyl name + halide •e.g. acetyl chloride (= ethanoyl chloride) butyryl bromide (= butanoyl bromide)2.6. NITRILES R-

CººººN

•hydrocarbon + suffix: -nitrile oralkyl cyanide •e.g ethanenitrile or methyl cyanide butanenitrile or propyl cyanide • mostly toxic liquids

Exercise

• H 2N-CH 2-CH 2-CH

2-COOH

• CH

3-CO-CH

2-COOH

• CH

3-CH(OH)-CH

2-COOH

• CH 3-CH 2-CH

2-CO-O-CH

3 • CH

3-CO-COOH

• CH3-CH

2-O-CH

3 • CH

3-CO-CH

2-CH 3 • CH 3-(CH

2)14-COOH

• CH 3-CH 2-CH

2-COONa

• (CH 3-CH

2-COO)

2Ca • CH 3-CH

2-O-CO-H

Exercise

• C 6H

5-CO-Cl

• H-CO-O-CH 2-CH 3 • CH

2=CH-CN

• H-CO-NH 2 • CH 3-CH

2-CO-NH-CH

2-CH 3

[PDF] Derivatives of carboxylic acids

Derivatives of carboxylic acids

Vladimíra Kvasnicová

Derivatives of carboxylic acids

2. functional derivatives

Substitutional derivatives

1.1. HALOGEN DERIVATIVES

R(X)- COOHX = Cl, Br, I, F

1.2. HYDROXY DERIVATIVES

R(OH)- COOH

Important hydroxy derivatives

1.3. OXO DERIVATIVES

1.4. AMINO DERIVATIVES

2)- COOH

Functional derivatives

2.1. SALTS

R- COO

2.2. ESTERS

R1- O-

2-CO-O-CH

3(apple)

2-CO-O-(CH

2)4-CH

3(apricot)

3-CO-O-(CH

2)4-CH

3(banana)

2-CO-O-CH

3(pineapple)

3(rum)

Examples of esters

Properties and reactions of esters

2.3. ANHYDRIDESR

1- CO- O- CO

2.4. AMIDES

CO- NH

2group:

N-alkyl...amide

2.5. ACYLHALIDES

X = halogen

CººººN

Exercise

2-COOH

3-CO-CH

2-COOH

3-CH(OH)-CH

2-COOH

2-CO-O-CH

3-CO-COOH

2-O-CH

3-CO-CH

2)14-COOH

2-COONa

2-COO)

2-O-CO-H

Exercise

5-CO-Cl

2=CH-CN

2-CO-NH-CH

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