Carboxylic Acids And Esters Flashcards
What is the functional group for carbocylic acids?
COOH
What is the functional group for esters?
COOR
What is the functional group for acyl chlorides?
CO-Cl
What is the functional group for acid anhydrydes?
OC-O-CO
What is the functional group for amides?
CO-NH2
What is the general formula for carboxylic acids?
CnH2nOH
Name 4 derivatives of carboxylic acids
Esters
Acyl chlorides
Amides
Acid anhydryde
Describe the melting points, solubility and acidity of carboxylic acids
High melting and boiling points- due to hydrogen bonding between molecules
Low Mr carboxylic acids are soluble in water- form hydrogen bonding with water
Weak acids- only partially dissociate (donate H+ ions) in water
Describe the test for carboxylic acids
Add sodium carbonate
If carboxylic acids are present, effervescence will be seen due to carbon dioxide
What is the general formula of esters?
CnH2nO2
What is a condensation reaction?
A reaction in whoch two molecules join together with the elimination of a small molecule
What are the reagents and conditions of the preparation of esters using carboxylic acids and alcohols?
Reagents- concentrated H2SO4
Heat
What are the conditions for the preparation of esters using
Alcohol and acid anhydrides?
Heat
What are the conditions for the preparation of esters using
Alcohol and acyl chlorides?
Room temperature
State three ways in which esters can be prepared using alcohol
Carboxylic acid and alcohol
Acyl chloride and alcohol
Acid anhydryde and alcohol
Compare the boiling points and solubility of esters and carboxylic acids
Esters have a lower bp and are less soluble than carboxylic acids as they do not form hydrogen bonds
Name four uses of esters
Perfumes
Sweets
Solvents
Plasticisers
What is aspirin?
An ester of 2-hydroxybenzoic acid
How can aspirin be manufactured? What else does this reaction produce?
By reacting ethanoic anhydide with 2-hydroxybenzoic acid. This also produces ethanoic acid
When manufactoring esters, why is ethanoic anhydride used instead of ethyl chloride?
It is less corrosive
Safer, as it produces ethanoic acid instead of HCL which is corrosive
Cheaper
Doesnt react with water as easily
What is hydrolysis?
The breaking of bonds using water
What are the reactants, products and conditions for the acid hydrolysis of esters?
Reactants- ester and water
Products- carboxylic acid and alcohol
Conditions- heat reflux with dilute H2SO4
What are the resctants, products snd conditions for the alkaline hydrolysis of esters?
Reactants- esters and NaOH
Products- alcohol and Na salt of carboxylic acid
Conditions- heat reflux, dilute NaOH
How can a carboxylic acid be obtained after the alkaline hydrolysis of esters?
By reacting the sodium salt with an acid
What is a triglyceride?
A triester of glycerol and fatty acids
What is the difference between fats and oils?
Fats are solid at room temp, as they contain saturated fatty acids
Oils are liwuid at room temp, as they contain insaturated fatty acids
Wha5 is the difference between saturated and unsaturated fatty acids?
Saturated fatty acids only contain single bonds between carbons, unsaturated contains double bonds
What are the conditions, reactants and products of the alkaline hydrolysis of triglycerides?
Reactants- triglyceride, 3NaOH
Products- glycerol, sodium salts of fatty acids
Conditions- heat reflux
What can the products of the hydrolysis of triglycerides be used for?
The sodium sakts of fatty acids can be used as soaps
What is biodiesel?
A mixture of methyl esters of long chain carboxylic acids
How can buodiesel be manufactured? And what are its conditions?
By reacting methanol with vegetable oil (triglyceride) in the presence of a catalyst- KOH.
What is the name for the manufacturing of biodiesel?
Trans Esterification
Out of alcojols. Aldehydes and carboxylic acids, which has the highest boiling point? Why?
Catboxylic acids as they form stronger hydrogen bonds between molecules that require more energy to be overcome
What is acylation?
Where an acyl group is introduced to another molecule
What is an acyl group?
A group with the formula R-C=O
-X
What are acid derivatives, give two examples
Acid derivatives are molecules with acyl groups
Acyl chloride and acid anhydrides
What is a nucleophile?
An electron pair donor
Are carboxylic acids or acid derivatives more reactive?
Acid derivatives are more reactive, due to the polarity of their carbonyl group.
They react with nucleophiles
What type opf reaction is the hydrolysis of acyl chloride? What are its products?
Nucleophilic addition elimination
Produces HCl and carbocylivc acids. This produces a solution with a low pH
What are the reagents and observations with the hydrolysis of acyl chlorides?
Reagents- water
Observations- HCl gives off steamy fumes
What are the products of reacting ammonia with acyl chlorides, and what is the mechanism?
Produces amides and HCl
Nucleophilic additiopn elimination
What are the products of reacting alcohols with acyl chlorides, and what is the mechanism?
Produces esters and HCl
Nucleophilic addition elimination
What are the products of reacting primary amines with acyl chlorides, and what is the mechanism?
Produces amides and HCl
Nucleophilic addition elimination
What are the products of reacting water with acid anhydrides, what is the type of reaction and what is the mechanism?
Produces two carboxylic acids
Hydrolysis reaction with nucleophilic addition elimination
What are the products of reacting ammonia with acid anhydrides, and what is the mechanism?
Produces a carboxylic acid and amide
Nucleophilic addition elimination reaction
What are the products of reacting primary amines with acid anhydrides, and what is the mechanism?
Produces an amide and carboxylic acid
Nucleophilic addition elimination
What are the products of reacting alcohol with acid anhydrides, and what is the mechanism?
Produces an ester and carbocyliuc acid
Nucleophilic addition elimination reaction
Why are nucleophilic addition eliminatiopn reactions with acid anhydrides better than with acyl chlorides?
Acyl chlorides produce HCl wi]hich is very corrosive, whereas acid anhydrides produce carboxyli acids, whioch are much less corrosive