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Module 7: Organic Chemistry
Quick questions on Esters, esterification and saponification explained: HSC Chemistry Module 7
13short Q&A pairs drawn directly from our worked dot-point answer. For full context and worked exam questions, read the parent dot-point page.
What is structure and naming?Show answer
An ester contains the linkage $-COO-$. The general formula is $R-COO-R'$, where $R$ comes from the carboxylic acid and $R'$ comes from the alcohol.
What is esterification (Fischer esterification)?Show answer
An alcohol reacts with a carboxylic acid in the presence of a concentrated $H_2SO_4$ catalyst, heated under reflux, to give an ester and water:
What is physical properties of esters?Show answer
Esters have a polar $C=O$ but no $O-H$, so they cannot hydrogen-bond to each other. Boiling points are lower than the parent acid and alcohol of similar molar mass, comparable to ketones. Small esters are volatile liquids with characteristic fruity smells.
What is hydrolysis?Show answer
Acid hydrolysis. Reflux the ester with dilute sulfuric acid; the reverse of esterification:
What is mechanism in brief?Show answer
Fischer esterification is acid-catalysed nucleophilic acyl substitution. The acid is protonated on the carbonyl O, the alcohol O attacks the carbonyl C, proton transfers occur, water leaves, and a proton is lost from the protonated ester. You do not need the full curly-arrow mechanism for HSC, but you do need to know what each reactant contributes.
What is purification?Show answer
Pour the cooled mixture into saturated sodium hydrogencarbonate to neutralise unreacted acid (effervescence stops when complete). Separate the organic layer, dry over anhydrous $MgSO_4$, then distil at the boiling point of the ester.
What is acid hydrolysis?Show answer
Reflux the ester with dilute sulfuric acid; the reverse of esterification:
What is base hydrolysis?Show answer
Reflux the ester with aqueous NaOH:
What is naming esters in the wrong order?Show answer
Always alkyl (from alcohol) first, then alkanoate (from acid). Do not write "ethanoate ethyl".
What is forgetting the equilibrium arrows?Show answer
Acid hydrolysis and esterification are reversible. Saponification is not. Get the arrows right.
What is using dilute $H_2SO_4$ for esterification?Show answer
You need concentrated $H_2SO_4$, both as catalyst and dehydrator. Dilute acid does not drive the equilibrium.
What is skipping the bicarbonate wash?Show answer
Without it, the product is contaminated with unreacted carboxylic acid and traces of $H_2SO_4$.
What is confusing transesterification with esterification?Show answer
Biodiesel is made by transesterification (swapping the alcohol on an existing ester), not by direct esterification of fatty acid plus methanol.