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Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution. Chapter 19. Assignment. Skip the following sections: 19.1, 19.11, 19.15, 19.16, 19.18, 19.21 and 19.32 These PowerPoint slides have been revised for Fall 2007. Some additional sections have been dropped or minimized!.

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assignment
Assignment
  • Skip the following sections:

19.1, 19.11, 19.15, 19.16, 19.18,

19.21 and 19.32

These PowerPoint slides have been revised for Fall 2007. Some additional sections

have been dropped or minimized!

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problem assignment
Problem Assignment
  • In-Text:

1 a, c 4, 5a - d, 6 a - c 8 a, c

9 -11 15 - 19 21 - 23 26, 27 31 - 40

  • End-of-Chapter:

4 6 - 9 15

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sect 19 2 19 3 and 19 4 nomenclature for acid chlorides acid anhydrides and esters
Sect. 19.2, 19.3 and 19.4Nomenclature for acid chlorides, acid anhydrides and esters

Only ester nomenclature on test!

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slide7

Acid part of ester

Alcohol part of ester

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slide8

Ethyl ethanoate (IUPAC)

Ethyl acetate (common)

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slide10
Ethyl pentanoate

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sect 19 5 and 19 6 nomenclature for amides and nitriles
Sect. 19.5 and 19.6: Nomenclature for amides and nitriles

Skip these sections! Not on test!

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sect 19 7 mechanisms
Sect. 19.7: Mechanisms

Base hydrolysis of an ester

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sect 19 8 19 9 preparation and reactions of acid chlorides
Sect. 19.8/ 19.9: Preparation and reactions of acid chlorides

Important!!! Acid chlorides are key

intermediates for making esters, amides

and anhydrides!!!!

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sect 19 10 reducing agents
Sect. 19.10: Reducing agents
  • Review of reductions on acid chlorides.
  • A look at the reduction of all the derivatives of carboxylic acids.
  • We talked about this in Chapter 16!

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reactions of sodium borohydride
Reactions of sodium borohydride
  • Aldehydes yield primary alcohols
  • Ketones yield secondary alcohols
  • Esters give no reaction!
  • Amides give no reaction!

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reactions of lithium aluminum hydride
Reactions of lithium aluminum hydride
  • Aldehydes give primary alcohols
  • Ketones give secondary alcohols
  • Esters give primary alcohols from the

carboxylic acid part of the ester (Sect 19.20)

  • Amides give primary amines!! (Sect 19.24)

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sect 19 11 skip
Sect. 19.11: skip

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sect 19 12 carboxylic acid derivatives
Sect. 19.12: carboxylic acid derivatives

Esters

Amides

Anhydrides

Nitriles

All of these functional groups will be hydrolyzed in acidic or basic water to give the parent carboxylic acid

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fischer esterification
Fischer Esterification

ESTERIFICATION REACTIONS ARE REVERSIBLE. You need

to push it to the right (ester) by removing water as it forms. This reaction is acid catalyzed

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sect 19 17 hydrolysis of esters
Sect. 19.17: Hydrolysis of Esters

See slide for section 19.7 for mechanism of base hydrolysis

Mechanism of the acid catalyzed hydrolysis reaction is the reverse of the Fischer esterification reaction!

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sect 19 18 skip
Sect. 19.18: skip

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slide34

Mechanism

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sect 19 20 reduction of esters
Sect. 19.20: Reduction of Esters

Lithium aluminum hydride gives the primary alcohol

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sect 19 21 skip
Sect. 19.21: skip

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amides continued
Amides, continued
  • Keep this section simple, skip the DCC stuff

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sect 19 24 reduction of amides
Sect. 19.24: Reduction of amides

amides give primary amines with lithium aluminum hydride.

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slide48

The remaining sections will not be

included on the third test.

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the fatty acids
The Fatty Acids

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sect 19 31 19 33 19 34
Sect. 19.31, 19.33, 19.34
  • soaps
  • proteins
  • condensation polymers

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wallace carothers commercialized nylon at dupont
Wallace Carothers- commercialized Nylon at DuPont

Source: Michigan State University, Department of Chemistry

http://www.chemistry.msu.edu/Portraits/PortraitsHH_collection.shtml

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functional group interconversions
Functional Group Interconversions

H2O

OH-

R’OH

H2O

H2O

SOCl2

R’OH

OH-

NH3

NR’2H

NH3

NR’2H

RCOOH

H2O

RCOOH

NH3

NR’2H

NH3

NR’2H

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