17. Organic II (ESTERS)
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Give the ester functional group for esters (eg methyl ethanoate)
RCOOR eg: CH3COOCH3 Methyl - comes from the alchohol Ethanoate - comes from the carboxyllic acid
Give the 3 ways to prepare esters
Carboxylic acid + alcohol ⇌ ester + water (reflux) Acyl chloride + alcohol –> ester + HCl (room temp) Acid anhydride + alcohol –> ester + carboxylic acid (room temp)
Give the chemical reactions of esters
They are unreactive - make or break them -Hydrolysis of esters in alkaline / acidic conditions Saponification - alkaline hydrolysis of esters to produce carboxylate salt and alchohol. Its used to make soaps Transesterification - An ester reacts with an alcohol to form a different ester
Give an example equation for the hydrolysis of a esters in acidic equations
Produces carboxylic acid and ester - this is the reverse to making an ester CH3COOC2H5 + H2O ⇌ CH3COOH + C2H5OH Note: this time we do NOT add H+ ions here as a reactant
Give an example equation for the hydrolysis of a esters in alkaline equations
CH3COOC2H5 + OH –> CH3COO- (aq) + C2H5OH Note: it is very important to include the aqueous sign as we DO NOT add the H20 in the reactant. We will also need to wash the product with an acid to get the carboxylic acid.
Give the monomers of polyester
Diols and dicarboxylic acids/ diacyl chlorides diols + dicarboxylic acids - the COOH at each end of the molecule join to an OH group of a diol so water would be eliminated diols + diacyl chlorides - HCl is eliminated
Describe the hydrolysis of polyesters
Acid hydrolysis: dicarboxylic acid monomers and diol monomers are reformed Alkaline hydrolysis: diol monomer is reformed, but the salt of the dicarboxylic acid is formed eg: COONa+ (Na is from the alkaline conditions)
Polyesters are…..
Condensation polymers (formed from condensation reactions)
Give 2 differences of acid and alkali hydrolysis of esters
Acid hydrolysis is reversible, alkali hydrolysis is irreversible The acid is a catalyst in acid hydrolysis and the alkali is a reactant in alkaline hydrolysis
Esters are prepared using carboxylic acids and alcohols. Explain why you add sodium hydrogen carbonate to the reaction mixture to allow the presence of an ester to be detected
Without sodium hydrogen carbonate, the smell of the carboxylic acid masks the smell of the ester. Therefore, on addition of sodium hydrogen carbonate, the carboxylic acid is neutralised, allowing for the pear/ glue like smell of ester to be detected