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Questions and Answers
What is the product formed when compound A (C4H8) reacts with hydrogen bromide?
What type of reaction is involved when compound B (C4H9Br) reacts with ammonia?
What is the compound C formed from the reaction between compound B and ammonia?
What is the product formed when compound C reacts with ethanoyl chloride?
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What happens when compound F is refluxed in acidified potassium dichromate?
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Which compound isolated (compound G) after refluxing compound F is slightly acidic?
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What is the product formed when compound G reacts with phosphorus pentachloride?
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Which functional group is present in compound D (C6H13NO) formed from the reaction with ethanoyl chloride?
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What type of reaction occurs when amides react with water in the presence of an acid catalyst?
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What are the substances formed when ammonia reacts with an acyl chloride?
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Study Notes
Addition-Elimination Reactions
- Addition-elimination reaction mechanism applies to reactions between nucleophiles and acyl chlorides, acid anhydrides, amides, amino acids, and carboxylic acids.
Acyl Chlorides
- Acyl chlorides are extremely reactive and react with moisture in the air to form carboxylic acids, releasing HCl gas.
- Reaction with water: RCOCl + H2O → RCOOH + HCl
- Reaction with alcohols: RCOCl + ROH → RCOOR + HCl
- Advantage of using acyl chlorides for esterification: 100% yield
- Disadvantage: releases toxic fumes of HCl and requires very dry conditions.
Compound A, B, and C
- Compound A (C3H5OCl) is a liquid that fumes in air and reacts violently with water to form Compound B (HCl) and a solution of Compound C (C3H6O2).
- pH of the mixture is 1.
Acid Anhydrides
- Acid anhydrides react similarly to acyl chlorides through nucleophilic addition-elimination reactions.
- Reaction with water: (RCO)2O + H2O → 2RCOOH
- Reaction with alcohols: (RCO)2O + ROH → RCOOR + RCOOH
- Advantage of using acid anhydrides over acyl chlorides: no release of toxic HCl gas.
Carboxylic Acids
- Carboxylic acids react with alcohols through acid-catalyzed nucleophilic addition-elimination reactions.
- Reaction: RCOOH + ROH → RCOOR + H2O
- Importance of removing water from esterification reactions: to prevent reversal of the reaction.
Amides
- Amides contain the C=O and –NH2 functionalities and can be synthesized by reacting ammonia with an acyl chloride or acid anhydride.
- Reaction: RCOCl + NH3 → RCONH2 + HCl
- N-substituted amides can be synthesized by reacting an amine with an acyl chloride.
- Amides react with water in the presence of an acid catalyst to form a carboxylic acid and ammonia.
Synoptic Questions
- Various reaction mechanisms and syntheses of compounds involving acyl chlorides, acid anhydrides, amides, and carboxylic acids.
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Description
Test your knowledge of addition-elimination reactions in organic chemistry, focusing on the reaction mechanisms involving nucleophiles and homologous series such as acyl chlorides, acid anhydrides, amides, amino acids, and carboxylic acids.
