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Fischer Esterification 1) Answer the table. 2) Write the equations involved in the chemical tests. 3) Conclusion

Fischer Esterification 1) Answer the table. 2) Write the equations involved in the chemical tests. 3) Conclusion

Organic Chemistry
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter16: Aldehydes And Ketones
Section: Chapter Questions
Problem 16.65P: All rearrangements we have discussed so far have involved generation of an electron-deficient carbon...
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Fischer Esterification 1) Answer the table. 2) Write the equations involved in the chemical tests. 3) Conclusion Video link: https://drive.google.com/file/d/1wMWprC_667c1B0TH-Dp7HNzQbDqxI6Ba/view?usp=sharing
Introduction: Alcohols can combine with many kinds of acids to form esters. When no type of acid is specified, the word ester is assumed to mean a carboxylic ester, the ester of an alcohol and a carboxylic acid. The reaction, called Fischer esterification, is characterized by the combining of an alcohol and an acid (with acid catalysis) to yield an ester plus water. Mechanism: R-1-CH HO- Under appropriate conditions, inorganic acids also react with alcohols to form esters. To form these esters, a wide variety of specialized reagents and conditions can be used. O acid L Procedures: 4) Water leaves 3) Proton transfer sulfuric acid 5) Deprotonation [CH+ H-O-RR-C-O-R¹ + [H−O¬H] N-CH+ H-O-R 2) Nucleophilic attack on the carbonyl R R с D CH + H-O-R HO Test tube A alcohol nitrio noid O HO-P-OH + H-O-RHO-P-O-R + H₂O CH phosphoric acid The overall reaction is reversible; to drive the reaction to completion, it is necessary to exploit Le Châteliers principle, which can be done either by continuously removing the water formed from the system or by using a large excess of the alcohol. 1) Protonation of the carbonyl by the acid. The carbonyl is now activated toward nucleophilic attack. HB H O H* H H - Test tube Carboxylic Acid ester o t an alkyl sulfate ester Carboxylic Acid Acetic Acid Acetic Acid Acetic Acid Salicylic -O-R+ H₂O N-O-R+ H₂O Alcohol O an alkyl nitrate ester O k-X- OH an alkyl phosphate ester R- https://drive.google.com/file/d/1wMWprC 667c180TH-Dp7HNzQbDqx16Ba/view?usp=sharing 1. Add 10 drops of liquid carboxylic acids sample in a separate clean test tube, then add 10 drops of alcohols in their designated test tubes: + H₂O HB Alcohol Akone Benzyl 2. Add 5 drops of Concentrated Sulfuric Acid (H,SO.) to each test tube and mix. CAUTION! Sulfuric acid causes severe burns. Flush any spill with lots of water. Use gloves with this reagent. Isopentyl Ethanol Methanol 3. Place the test tubes in a warm water bath at 60-C for 15 min. 4. Waft the fumes towards your face to note the odor of the esters formed in each of the test tubes. II. Observations: Observation Odor
Transcribed Image Text:Introduction: Alcohols can combine with many kinds of acids to form esters. When no type of acid is specified, the word ester is assumed to mean a carboxylic ester, the ester of an alcohol and a carboxylic acid. The reaction, called Fischer esterification, is characterized by the combining of an alcohol and an acid (with acid catalysis) to yield an ester plus water. Mechanism: R-1-CH HO- Under appropriate conditions, inorganic acids also react with alcohols to form esters. To form these esters, a wide variety of specialized reagents and conditions can be used. O acid L Procedures: 4) Water leaves 3) Proton transfer sulfuric acid 5) Deprotonation [CH+ H-O-RR-C-O-R¹ + [H−O¬H] N-CH+ H-O-R 2) Nucleophilic attack on the carbonyl R R с D CH + H-O-R HO Test tube A alcohol nitrio noid O HO-P-OH + H-O-RHO-P-O-R + H₂O CH phosphoric acid The overall reaction is reversible; to drive the reaction to completion, it is necessary to exploit Le Châteliers principle, which can be done either by continuously removing the water formed from the system or by using a large excess of the alcohol. 1) Protonation of the carbonyl by the acid. The carbonyl is now activated toward nucleophilic attack. HB H O H* H H - Test tube Carboxylic Acid ester o t an alkyl sulfate ester Carboxylic Acid Acetic Acid Acetic Acid Acetic Acid Salicylic -O-R+ H₂O N-O-R+ H₂O Alcohol O an alkyl nitrate ester O k-X- OH an alkyl phosphate ester R- https://drive.google.com/file/d/1wMWprC 667c180TH-Dp7HNzQbDqx16Ba/view?usp=sharing 1. Add 10 drops of liquid carboxylic acids sample in a separate clean test tube, then add 10 drops of alcohols in their designated test tubes: + H₂O HB Alcohol Akone Benzyl 2. Add 5 drops of Concentrated Sulfuric Acid (H,SO.) to each test tube and mix. CAUTION! Sulfuric acid causes severe burns. Flush any spill with lots of water. Use gloves with this reagent. Isopentyl Ethanol Methanol 3. Place the test tubes in a warm water bath at 60-C for 15 min. 4. Waft the fumes towards your face to note the odor of the esters formed in each of the test tubes. II. Observations: Observation Odor
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