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A comprehensive overview of five classes of organic compounds related to carboxylic acids: acid halides, sulfonyl chlorides, acid anhydrides, esters, and amides. It covers the structure, nomenclature, and characteristic reactions of these compounds, including hydrolysis, esterification, and reduction. The document also discusses the relative reactivities of these acid derivatives and their applications in organic synthesis. The detailed explanations and step-by-step reaction mechanisms make this document a valuable resource for students and researchers studying organic chemistry, particularly in the areas of functional group transformations and synthetic methodology.
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RC-OH H-Cl H-OR' H-NH 2
RCCl
Th e enol of an amide
A n acid chloride
An acid An ester anhydride
An amide A nitrile
H 3 C S-OH
O
O
H 3 C S-Cl
O
O
CH 3 -S-Cl
O
O
CH 3 -S-OH
O
O Methanes ulfon ic acid
p- Toluen esulfon ic acid
Methanes ulfonyl ch loride (Mesyl ch loride, MsCl)
p- Toluen esulfon yl chloride (Tosyl chlorid e, TsCl)
Acetic anh ydrid e Benzoic anh ydride
Triphosphoric acid
Diphosphate ion (Pyrophosphate ion)
Diphosphoric acid (Pyrophosphoric acid)
Triphosphate ion
EtO O
OEt
Ethyl ethan oate (Ethyl acetate)
D iethyl butaned ioate (D ieth yl s uccin ate)
Is op ropyl ben zoate
OCH 3
CH 3 O-P-O-
O C-H CH 2 -O-P-O-
CHO HO
O-
O
N
HO
H 3 C
CH 2 O-P-O- O-
CHO O CO- C CH 2
O P O- O-
O
O
Glyceraldehyde 3-ph os phate
Pyrid oxal p hos phate (^) Phosp hoenol- p yruvate
D imethyl p hosph ate
CH 3 CNH 2
O CH 3 C-N
H
CH 3
O H-C-N
CH 3
CH 3
O
N- Methylacetamide (a 2° amid e)
Acetamide (a 1° amide)
N,N- D imethyl- formamid e (DMF) (a 3° amide)
Amoxicillin (a -lactam an tib iotic)
The penicillin s differ in the grou p bond ed to the acyl carb on -lactam
2
p K a 10 p K a 9.7 p K a 8.
Acetamide Ben zenesu lfonamide Succinimide Phth alimide p K a 15-
O
O
N N
O
O
A resonance-stabi l i zed an i on
N
O
O
S
NH
O
O O S accharin
N-^ NH 4 +
O
O O S accharin
A water-soluble ammonium salt