Download presentation
Presentation is loading. Please wait.
1
Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution
Chapter 19 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution WWU-Chemistry
2
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 Some additional sections have been dropped or minimized! WWU-Chemistry
3
Problem Assignment In-Text: 1 a, c 4, 5a - d, 6 a - c 8 a, c
, End-of-Chapter: WWU-Chemistry
4
The addition/elimination mechanism
WWU-Chemistry
5
Nucleophilic Acyl Substitution
WWU-Chemistry
6
Sect. 19.2, 19.3 and 19.4 Nomenclature for acid chlorides, acid anhydrides and esters
Only ester nomenclature on test! WWU-Chemistry
7
Acid part of ester Alcohol part of ester WWU-Chemistry
8
Ethyl ethanoate (IUPAC)
Ethyl acetate (common) WWU-Chemistry
9
Methyl 2-methylpropanoate
WWU-Chemistry
10
Ethyl pentanoate WWU-Chemistry
11
Methyl cyclohexanecarboxylate
WWU-Chemistry
12
Isopropyl benzoate or 2-methylethyl benzoate
WWU-Chemistry
13
Ethyl 5-bromo-3,4-dimethylhexanoate
WWU-Chemistry
14
Ethyl 5-bromo-3,4-dimethyl-2,4-hexadienoate
WWU-Chemistry
15
Sect. 19.5 and 19.6: Nomenclature for amides and nitriles
Skip these sections! Not on test! WWU-Chemistry
16
Sect. 19.7: Mechanisms Base hydrolysis of an ester WWU-Chemistry
17
Sect. 19.8/ 19.9: Preparation and reactions of acid chlorides
Important!!! Acid chlorides are key intermediates for making esters, amides and anhydrides!!!! WWU-Chemistry
18
Preparation of an Ester
WWU-Chemistry
19
Preparation of an Amide
WWU-Chemistry
20
Preparation of an Anhydride
WWU-Chemistry
21
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! WWU-Chemistry
22
Reactions of sodium borohydride
Aldehydes yield primary alcohols Ketones yield secondary alcohols Esters give no reaction! Amides give no reaction! WWU-Chemistry
23
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) WWU-Chemistry
24
Sect : skip WWU-Chemistry
25
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 WWU-Chemistry
26
Sect and 9.14: Esters WWU-Chemistry
27
Esters as Flavoring Substances
WWU-Chemistry
28
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 WWU-Chemistry
29
Fischer esterification is an acid catalyzed reaction
WWU-Chemistry
30
Sect and skip WWU-Chemistry
31
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! WWU-Chemistry
32
Sect : skip WWU-Chemistry
33
Sect. 19.19: Reaction of Esters with Organometallic Reagents
WWU-Chemistry
34
Mechanism WWU-Chemistry
35
Sect. 19.20: Reduction of Esters
Lithium aluminum hydride gives the primary alcohol WWU-Chemistry
36
Diisobutylaluminum hydride (DibalH) gives the aldehyde
WWU-Chemistry
37
Sect : skip WWU-Chemistry
38
Sect. 19.22 and 19.23: Preparation and Reactions of Amides
Heat WWU-Chemistry
39
Remember, also prepare amides from acid chlorides
WWU-Chemistry
40
Amides, continued Keep this section simple, skip the DCC stuff
WWU-Chemistry
41
Sect. 19.24: Reduction of amides
amides give primary amines with lithium aluminum hydride. WWU-Chemistry
42
Sect. 19.25 and 19.26: Reactions of anhydrides
WWU-Chemistry
43
Preparation of aspirin and acetaminophen (Tylenol)
WWU-Chemistry
44
Sect. 19.27 and 19.28: preparation and reactions of nitriles
WWU-Chemistry
45
Base-Promoted Hydrolysis of a Nitrile (Part One)
WWU-Chemistry
46
Base-Promoted Hydrolysis of a Nitrile (Part Two)
WWU-Chemistry
47
Sect. 19.29: reduction of nitriles with lithium aluminum hydride and Hydrogen
WWU-Chemistry
48
The remaining sections will not be included on the third test.
WWU-Chemistry
49
Sect. 19.30: Fats and oils (Triglycerides)
WWU-Chemistry
50
The Fatty Acids WWU-Chemistry
51
Sect. 19.31, 19.33, 19.34 soaps proteins condensation polymers
WWU-Chemistry
52
Wallace Carothers- commercialized Nylon at DuPont
Source: Michigan State University, Department of Chemistry WWU-Chemistry
53
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 WWU-Chemistry
Similar presentations
