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COOH derivitives + structure in reactivity order
- Acid Halide (R-C=OX)
- Acid Anhydride (R-C=O-O-C=O-R
- Ester (R-C=O-R') | Acid
- Amide (R-C=O-NH2)
- Nitrile (R-C=N)
Naming COOH derivitives
- Start with acid name...
- Acid Halide: drop "-ic acid" add "-yl <halide>"
- Symmetrical Anyhdrides: drop "acid" add "anhydride"
- Unsymmetrical anyhydrides: name BOTH acids, drop "-acid", alpha order, add "anhydride"
- Esters: Name alkyl group, name acid, drop "-ic acid" add "-ate"
- Amide: drop "ic acid" or "-oic acid" add "-amide"
- Nitriles: "drop -ic acid or "oic acid" add "-onitrile"
Conversion between COOH derivitives
- (U) Acid + SOCl2 --> Acid chloride
- Acid Chloride + acid<--> anyhydride
- Acid Chloride + alcohol --> ester
- Acid Chloride + water <--> Acid
- Acid Chloride + 2NH3 <--> amide
- 2Acid + heat --> Anyhdride
- Anhydride + alcohol --> ester + acid
- Anydride + Amine --> Amide + acid
- Anhydride + water --> 2 acids
- EsterR' + alcoholR <-H or OH-> EsterR + alcoholR'
- Ester + amine <--> amide
- Ester + water --> acid + alcohol
(U) Amide + H2O --> Acid
Why is nitrile considered a COOH derivitive?
reduced to amide then to acid during hydrolysis
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