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Questions and Answers
What is the common feature of all acid derivatives?
What is the common feature of all acid derivatives?
What is the purpose of using sulphur dichloride oxide in the preparation of acid chlorides?
What is the purpose of using sulphur dichloride oxide in the preparation of acid chlorides?
What is the product of the reduction of carboxylic acids using lithium tetrahydridoaluminate(III) in dry ethoxyethane?
What is the product of the reduction of carboxylic acids using lithium tetrahydridoaluminate(III) in dry ethoxyethane?
What is the catalyst used in the chlorination of ethanoic acid to form monochloroethanoic acid?
What is the catalyst used in the chlorination of ethanoic acid to form monochloroethanoic acid?
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What is the reason why carboxylic acids cannot be reduced to the corresponding aldehyde directly?
What is the reason why carboxylic acids cannot be reduced to the corresponding aldehyde directly?
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What is the characteristic of acid chlorides?
What is the characteristic of acid chlorides?
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What is the reaction involved in the preparation of acid chlorides?
What is the reaction involved in the preparation of acid chlorides?
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What is the intermediate formed in the reduction of carboxylic acids using lithium tetrahydridoaluminate(III) in dry ethoxyethane?
What is the intermediate formed in the reduction of carboxylic acids using lithium tetrahydridoaluminate(III) in dry ethoxyethane?
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Why are nitriles considered as acid derivatives?
Why are nitriles considered as acid derivatives?
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What is the purpose of using lithium tetrahydridoaluminate(III) in dry ethoxyethane in the reduction of carboxylic acids?
What is the purpose of using lithium tetrahydridoaluminate(III) in dry ethoxyethane in the reduction of carboxylic acids?
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Study Notes
Nucleophilic Acyl Substitution
- Carbonyl groups readily undergo nucleophilic attacks from nucleophiles such as –OH, –OR’, and –NH2.
- Reaction of acid chlorides with alcohols exemplifies nucleophilic acyl substitution, or acylation.
- Nucleophilic substitution of the ethanoyl group (CH3CO-) is termed ethanoylation.
- The mechanism includes nucleophile addition followed by elimination of chloride, similar to condensation reactions.
Hydrolysis of Acid Chlorides
- Aliphatic acid chlorides hydrolyze vigorously in cold water, forming carboxylic acids and hydrogen chloride.
- Acid chlorides produce hydrogen chloride when exposed to moist air.
- Aromatic acid chlorides hydrolyze at a slower rate compared to aliphatic counterparts.
Ester Formation
- Acid chlorides react with alcohols and phenols to form esters along with hydrogen chloride.
- These esterification reactions can be performed using carboxylic acids and alcohols in the presence of concentrated sulfuric acid.
- The reaction of acid chlorides or acid anhydrides with alcohols is preferred for producing esters as it is faster and proceeds to completion.
Reactions with Ammonia and Amines
- Acid chlorides react with ammonia and amines, yielding amides and substituted amides, respectively.
Acid Anhydrides
- Acid chlorides yield acid anhydrides when distilled with the sodium salt of a carboxylic acid.
- Acid anhydrides are colorless liquids with pungent odors, similar to acid chlorides.
- Mixed acid anhydrides can be prepared through a reaction between an acid chloride and the sodium salt of another carboxylic acid.
Hydrolysis and Reactivity of Acid Anhydrides
- Acid anhydrides undergo nucleophilic substitution at a slower rate compared to acid chlorides.
- They hydrolyze to produce carboxylic acids.
- They react with alcohols and phenols, yielding esters and carboxylic acids.
- Ammonia and amines react with acid anhydrides to form amides and substituted amides.
Properties and Hydrolysis of Esters
- Lower esters are colorless liquids that emit fruity odors.
- Esters are generally insoluble in water but soluble in organic solvents.
- Hydrolysis of esters occurs when they are refluxed with dilute mineral acids or dilute alkali, reversing the esterification process to yield carboxylic acids and alcohols.
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Description
Learn about the mechanism of nucleophilic acyl substitution, a type of reaction involving the addition of a nucleophile to an acyl compound. Understand the reaction of acid chlorides with alcohols and the concept of ethanoylation.
