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Functional Derivatives of Carboxylic Acids. Nomenclature: the functional derivatives’ names are derived from the common or IUPAC names of the corresponding carboxylic acids. Acid chlorides : change –ic acid to –yl chloride Anhydrides : change acid to anhydride.

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Presentation Transcript
slide2

Nomenclature: the functional derivatives’ names are derived from the common or IUPAC names of the corresponding carboxylic acids.

Acid chlorides: change –ic acid to –yl chloride

Anhydrides: change acid to anhydride

slide3

Amides: change –ic acid (common name) to –amide

-oic acid (IUPAC) to –amide

Esters: change –ic acid to –ate preceded by the name of the alcohol group

slide7

nucleophilic acyl substitution vs nucleophilic addition to carbonyl

aldehydes & ketones – nucleophilic addition

functional deriv. of carboxylic acids – nucleophilic acyl substitution

slide8

Acid Chlorides

Syntheses:

SOCl2

RCOOH + PCl3 RCOCl

PCl5

slide9

Acid chlorides, reactions:

  • Conversion into acids and derivatives:
  • a) hydrolysis
  • b) ammonolysis
  • c) alcoholysis
  • Friedel-Crafts acylation
  • Coupling with lithium dialkylcopper
  • Reduction
slide11

Schotten-Baumann technique – aromatic acid chlorides are less reactive than aliphatic acid chlorides. In order to speed up the reactions of aromatic acid chlorides, bases such as NaOH or pyridine are often added to the reaction mixture.

slide15

Anhydrides, syntheses:

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  • Anhydrides, reactions:
  • Conversion into carboxylic acids and derivatives.
  • a) hydrolysis
  • b) ammonolysis
  • c) alcoholysis
  • 2) Friedel-Crafts acylation
slide18

Amides, synthesis:

Indirectly via acid chlorides.

slide19

Amides, reactions.

1) Hydrolysis.

slide21

Wool, hair, silk, spider web: fibrous proteins.

Silk is an extremely strong, thin, lightweight fiber, perfect for making sheer stockings for women as well as parachutes. It is made by the silkworm, a domesticated moth larva raised in Japan and China. During World War II a substitute material was needed and developed by DuPont – Nylon-66, a synthetic polyamide of adipic acid and hexamethylenediamine:

slide22

Esters, syntheses:

  • From acids
  • RCO2H + R’OH, H+ RCO2R’ + H2O
  • From acid chlorides and anhydrides
  • RCOCl + R’OH RCO2R’ + HCl
  • From esters (transesterification)
  • RCO2R’ + R”OH, H+ RCO2R” + R’OH
  • RCO2R’ + R”ONa RCO2R” + R’ONa
slide23

Esters often have “fruity” or “floral” odors:

isopentyl acetate banana oil

n-pentyl butyrate apricot

isopentyl isovalerate apple

ethyl butyrate peach

ethyl heptanoate cognac

ethyl nonate flower bouquet

ethyl laurate tuberose

methyl butyrate pineapple

octyl acetate orange

slide24

“Direct” esterification is reversible and requires use of LeChatelier’s principle to shift the equilibrium towards the products. “Indirect” is non-reversible.

slide26

Esters, reactions:

  • Conversion into acids and derivatives
  • a) hydrolysis
  • b) ammonolysis
  • c) alcoholysis
  • Reaction with Grignard reagents
  • Reduction
  • a) catalytic
  • b) chemical
  • 4) Claisen condensation
slide32

Esters, reduction

  • catalytic
  • chemical
slide34

Spectroscopy:

Infrared: strong absorbance ~ 1700 cm-1 for C=O

RCO2R 1740 ArCO2R 1715-1730 RCO2Ar 1770

Esters also show a strong C—O stretch at 1050-1300

Amides show N—H stretch at 3050 –3550 and N—H bend in the 1600-1640 region.

Nmr: NB in esters the protons on the alcohol side of the functional group resonate at lower field than the ones on the acid side.

RCOO—C—H 3.7 – 4.1 ppm

H—C—COOR 2 – 2.2 ppm

slide36

butyramide

C=O

N—H

N—H bend

slide37

Ethyl acetate

CH3CO2CH2CH3

b c a

Note which hydrogens are upfield.

c b a

slide38

Methyl propionate

CH3CH2CO2CH3

a b c

Note which hydrogens are upfield.

c b a