Ch21. Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions Nucleophilic Acyl Substitution Reactions of Acid Halides, Acid Anhydrides - Hydrolysis: Conversion into Carboxylic Acids RCOCI + H₂O RCO₂H + HCI - Conversion to Esters RCOCI + R'OH → RCO₂R' + HCI obs H₂O - Reduction (hydride attack, LiAIH4): Conversion into Alcohols (final product) CI 1) LIAIH4 2) H - Reaction with Grignard reagents, R-MgBr (1 equv. to ketone, or excess to alcohol) Reactions of Esters - Hydrolysis: Conversion of Esters into Carboxylic Acids by Aqueous Base (mechanism!) - Hydrolysis: Conversion of Esters into Carboxylic Acids by Aqueous Acid (mechanism!) NaOH, H₂O HCI, H₂O (A) (B)
Ch21. Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions Nucleophilic Acyl Substitution Reactions of Acid Halides, Acid Anhydrides - Hydrolysis: Conversion into Carboxylic Acids RCOCI + H₂O RCO₂H + HCI - Conversion to Esters RCOCI + R'OH → RCO₂R' + HCI obs H₂O - Reduction (hydride attack, LiAIH4): Conversion into Alcohols (final product) CI 1) LIAIH4 2) H - Reaction with Grignard reagents, R-MgBr (1 equv. to ketone, or excess to alcohol) Reactions of Esters - Hydrolysis: Conversion of Esters into Carboxylic Acids by Aqueous Base (mechanism!) - Hydrolysis: Conversion of Esters into Carboxylic Acids by Aqueous Acid (mechanism!) NaOH, H₂O HCI, H₂O (A) (B)
Chapter21: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
Section21.SE: Something Extra
Problem 75AP: One frequently used method for preparing methyl esters is by reaction of carboxylic acids with...
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Please complete boxed reactions. Thanks. P.s. this is not graded work but a study guide.
Transcribed Image Text:Ch21. Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
Nucleophilic Acyl Substitution
Reactions of Acid Halides, Acid Anhydrides
- Hydrolysis: Conversion into Carboxylic Acids
RCOCI+ H₂O → RCO₂H + HCI
- Conversion to Esters
RCOCI + R'OH → RCO₂R' + HCI
H₂O
- Reduction (hydride attack, LiAlH4): Conversion into Alcohols (final product)
1) LIAIH4
+
2) H
- Reaction with Grignard reagents, R-MgBr (1 equv. to ketone, or excess to alcohol)
Reactions of Esters
- Hydrolysis: Conversion of Esters into Carboxylic Acids by Aqueous Base (mechanism!)
- Hydrolysis: Conversion of Esters into Carboxylic Acids by Aqueous Acid (mechanism!)
NaOH, H₂O
HCI, H₂O
(A)
(B)
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