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Home › AS & A Level Chemistry › Unit 18: Organic Chemistry

Carboxylic Acids and Derivatives

Organic Chemistry Weightage: AS · Papers 1 and 2 (assumed in Paper 4) Topic 18
“Welcome! Carboxylic acids are weak acids that behave like any other acid with metals, alkalis and carbonates. They are made by oxidation or by hydrolysis, reduced by LiAlH4 to primary alcohols, and joined to alcohols to make esters, which hydrolyse back again. Learn each change as reagent, conditions and product, and keep acid hydrolysis (reversible) apart from alkali hydrolysis (complete).”
— SCORECHEM ACADEMIC TEAM

0. What Examiners Want

How marks are earned in Carboxylic Acids and Derivatives
  • Reagents and conditions: acidified K2Cr2O7 or KMnO4 under reflux; dilute HCl or H2SO4 or NaOH(aq) under reflux for hydrolysis; concentrated H2SO4 and reflux for esterification; LiAlH4 in dry ether.
  • Equations: salt formation with a metal, an alkali and a carbonate; nitrile and ester hydrolysis; esterification (with an equilibrium sign); reduction with [H]. All must balance.
  • Naming: carboxylic acids (-oic acid), carboxylate salts (-oate) and esters (alkyl -oate, in the right order).
  • Calculations: moles of acid from a mass, moles of gas from a volume at room conditions (24.0 dm3) or s.t.p. (22.4 dm3), and an Mr or percentage composition to identify an acid or an ester. Use the Periodic Table and the gas volumes in the Data Booklet.
  • Deduction and linking: choose a route of two or three steps using Topics 15 to 18, and identify an ester from its hydrolysis products.

Where this topic appears. Recent AS papers have asked for: the products when LiAlH4 reduces an acid (and the fact that it does not reduce a C=C bond); the pair of hydrolysis products of an ester that contains a given percentage of oxygen; the sodium salt formed when ethyl butanoate is hydrolysed by dilute NaOH; the Mr of an acid from the mass reacting with magnesium and the volume of H2 at s.t.p.; a sequence in which propanoic acid is reduced and the product is dehydrated; the table comparing hydrolysis of an ester with alkali and with acid; propanoic acid made from chloroethane through a nitrile, the equation of the acid with calcium and its conditions when made from propan-1-ol; and a route from a halogenoalkane through KCN, nitrile hydrolysis and esterification. Infrared absorptions of O–H and C=O in acids and esters are met in Topic 22.

1. Structure, Naming and Weak-Acid Behaviour

A carboxylic acid contains the carboxyl group, –COOH: a C=O and an O–H on the same carbon atom. The carbon is sp2 hybridised and planar. The acid is named from the alkane with -oic acid, and the COOH carbon is always C1, so no number is needed for it.

CARBOXYL GROUP, –COOHDiagram showing: CARBOXYL GROUP, –COOH; C; O; δ+; δ−; R; OH; C=O and O–H on the SAME carbon; carbon is sp2​: planar, about 120°; H-bonds between molecules: b.p. high; small acids dissolve in water; NAMING; name: alkane − e + -oic acid; the COOH carbon is C1 (no number) CARBOXYL GROUP, –COOH C O δ+ δ− R OH C=O and O–H on the SAME carbon carbon is sp2​: planar, about 120° H-bonds between molecules: b.p. high small acids dissolve in water NAMING name: alkane − e + -oic acid the COOH carbon is C1 (no number) HCOOH methanoic acid CH3​COOH ethanoic acid CH3​CH2​COOH propanoic acid salt: -oate, e.g. sodium ethanoate WEAK ACID: only a small fraction of the molecules ionise in water CH3​COOH(aq) ⇌ CH3​COO−​(aq) + H+​(aq) Ka​ (ethanoic acid) = 1.7 × 10−5​ mol dm−3​: mostly un-ionised molecules A strong acid ionises completely: HCl → H+​ + Cl−​. Same concentration, so lower [H+​] and higher pH for the weak acid.
The carboxyl group combines C=O and O–H on one carbon. Carboxylic acids are named with -oic acid and form -oate salts. They are weak acids: the equilibrium lies far to the left, so the solution contains mainly un-ionised molecules.
Acid Formula Salt (with sodium)
methanoic acid HCOOH sodium methanoate
ethanoic acid CH3COOH sodium ethanoate
propanoic acid CH3CH2COOH sodium propanoate
butanoic acid CH3CH2CH2COOH sodium butanoate

Properties. The O–H group and the C=O group let acid molecules form hydrogen bonds with one another and with water. As a result carboxylic acids have higher boiling points than alcohols or aldehydes of similar Mr, and the smaller ones mix with water.

Weak acids. In water a small proportion of the molecules ionise to give H+:

CH3COOH(aq) ⇌ CH3COO−(aq) + H+(aq)

The equilibrium lies far to the left (Ka for ethanoic acid is 1.7 × 10−5 mol dm−3), so the solution has a pH below 7 but higher than that of a strong acid of the same concentration, and contains mainly un-ionised molecules. A strong acid such as HCl ionises completely. This explains why ethanoic acid reacts more slowly with magnesium than hydrochloric acid of the same concentration: its H+ concentration is lower, but the reaction still goes to completion as the equilibrium shifts.

⚠️ Examiner Trap: Weak does not mean dilute. ‘Weak’ describes how far the acid ionises, and ‘dilute’ describes how much acid is dissolved. Write ‘partially ionised (partially dissociated)’ and use the ⇌ sign, not →. A weak acid reacts with a carbonate or a metal just as completely as a strong acid does, and gives the same amount of gas, because the equilibrium moves to the right as H+ is used up.

2. Making Carboxylic Acids

primary alcohol or aldehydeDiagram showing: primary alcohol or aldehyde; RCH2​OH or RCHO; excess acidified K2​Cr2​O7​; or KMnO4​, REFLUX; carboxylic acid; RCOOH; nitrile; R–C≡N; dilute HCl or H2​SO4​,; heat under reflux; carboxylic acid; RCOOH; ester; RCOOR′ primary alcohol or aldehyde RCH2​OH or RCHO excess acidified K2​Cr2​O7​ or KMnO4​, REFLUX carboxylic acid RCOOH nitrile R–C≡N dilute HCl or H2​SO4​, heat under reflux carboxylic acid RCOOH ester RCOOR′ dilute acid, reflux (or NaOH(aq), then H+​) carboxylic acid RCOOH + R′OH With NaOH(aq) a nitrile or ester gives the SALT, RCOO−​ Na+​ (plus NH3​ or R′OH). Add dilute HCl or H2​SO4​ afterwards to release the free carboxylic acid.
Three ways to make a carboxylic acid. Oxidation needs reflux and excess oxidant (a primary alcohol goes through the aldehyde to the acid); hydrolysis of a nitrile converts –CN into –COOH with no change in the carbon chain; hydrolysis of an ester gives the acid and the alcohol.

Oxidation of a primary alcohol or an aldehyde. Heat under reflux with excess acidified potassium dichromate(VI) (or acidified potassium manganate(VII)). The orange dichromate ions are reduced to green Cr3+. Using [O] for the oxidising agent:

Reflux keeps the volatile aldehyde in the flask so that it is oxidised right through. Distilling it off as it forms (Topic 17) would stop the oxidation at the aldehyde. A secondary alcohol gives a ketone, not an acid, and a tertiary alcohol is not oxidised.

Hydrolysis of a nitrile. The nitrile carbon becomes the carboxyl carbon, so the chain length is unchanged: propanenitrile, CH3CH2CN, gives propanoic acid.

Hydrolysis of an ester. Reflux with dilute acid gives the carboxylic acid and the alcohol; reflux with dilute NaOH gives the salt, and acidifying releases the acid (Section 6).

Making a nitrile. A halogenoalkane is heated under reflux with KCN in ethanol (Topic 15): CH3CH2Br + KCN → CH3CH2CN + KBr. The sequence halogenoalkane → nitrile → carboxylic acid adds one carbon atom to the chain. (The other route to a nitrile, from an aldehyde or ketone with HCN, is in Topic 17.)

⚠️ Examiner Trap: Reflux, excess, and the right oxidant. To reach the acid say ‘heat under reflux with excess acidified potassium dichromate(VI)’. Write dichromate(VI), K2Cr2O7, not ‘chromate’. For a nitrile, remember that hydrolysis with alkali gives the salt, and that the number of carbons in the product acid equals the number in the nitrile (propanenitrile gives propanoic acid, not butanoic acid).

3. Reactions of Carboxylic Acids as Acids

ReactantDiagram showing: Reactant; Equation (ethanoic acid); Observation; reactive metal; (e.g. Mg); 2CH3​COOH + Mg → (CH3​COO)2​Mg + H2​; bubbles of H2​;; metal dissolves; alkali; (e.g. NaOH); CH3​COOH + NaOH → CH3​COONa + H2​O; salt and water;; no visible change; carbonate Reactant Equation (ethanoic acid) Observation reactive metal (e.g. Mg) 2CH3​COOH + Mg → (CH3​COO)2​Mg + H2​ bubbles of H2​; metal dissolves alkali (e.g. NaOH) CH3​COOH + NaOH → CH3​COONa + H2​O salt and water; no visible change carbonate (e.g. Na2​CO3​) 2CH3​COOH + Na2​CO3​ → 2CH3​COONa + H2​O + CO2​ effervescence of CO2​ (limewater turns milky) Salt names end in -oate: sodium ethanoate, magnesium ethanoate. Gas volume (Data Booklet): 24.0 dm3​ mol−1​ at room T and p; 22.4 dm3​ mol−1​ at s.t.p. 2 mol of CH3​COOH give 1 mol of H2​ (with Mg) or 1 mol of CO2​ (with Na2​CO3​). Unreactive metals such as Cu do not react.
Carboxylic acids show the typical reactions of an acid because they release H+. Each gives a carboxylate salt: with a reactive metal also H2, with an alkali also water, and with a carbonate also water and carbon dioxide.

Because they release H+, carboxylic acids show the typical reactions of an acid. Each gives a carboxylate salt:

Worked example (using the Data Booklet). A 0.600 g sample of ethanoic acid reacts with excess magnesium. What volume of hydrogen is produced at s.t.p.?

  1. Mr of CH3COOH = 2 × 12.0 + 4 × 1.0 + 2 × 16.0 = 60.0 (Ar values from the Periodic Table in the Data Booklet).
  2. Amount of acid = 0.600 / 60.0 = 0.0100 mol.
  3. From the equation 2 mol of acid give 1 mol of H2, so amount of H2 = 0.00500 mol.
  4. At s.t.p. one mole of gas occupies 22.4 dm3 (Data Booklet), so volume = 0.00500 × 22.4 = 0.112 dm3 = 112 cm3. At room temperature and pressure the molar volume is 24.0 dm3, which would give 120 cm3.

Working backwards. If a known mass of a monoprotic acid gives a measured volume of gas, find the amount of gas, double it (for hydrogen) to get the amount of acid, then divide the mass by that amount to get Mr. Check whether the acid is monoprotic (one COOH) or dibasic (two COOH): a dibasic acid gives twice as much hydrogen per mole.

⚠️ Examiner Trap: Which molar volume? Read the question for ‘s.t.p.’ (22.4 dm3 mol−1) or ‘room temperature and pressure’ (24.0 dm3 mol−1) and take the value from the Data Booklet. Convert cm3 to dm3 by dividing by 1000. Do not forget the mole ratio: 2 mol of CH3COOH make only 1 mol of H2 or CO2.

4. Reduction to Primary Alcohols

carboxylic acidDiagram showing: carboxylic acid; CH3​COOH; ethanoic acid; + 4[H]; LiAlH4​ in DRY ether; primary alcohol; CH3​CH2​OH + H2​O; ethanol; General: RCOOH + 4[H] → RCH2​OH + H2​O (aldehyde: RCHO + 2[H] → RCH2​OH); LiAlH4​: WORKS; dissolved in DRY ether, room T; reacts… carboxylic acid CH3​COOH ethanoic acid + 4[H] LiAlH4​ in DRY ether primary alcohol CH3​CH2​OH + H2​O ethanol General: RCOOH + 4[H] → RCH2​OH + H2​O (aldehyde: RCHO + 2[H] → RCH2​OH) LiAlH4​: WORKS dissolved in DRY ether, room T reacts violently with water reduces C=O of acids, aldehydes, ketones does NOT reduce C=C NaBH4​: does NOT reduce acids too weak a reducing agent a carboxylic acid is left unchanged use it only for aldehydes and ketones (Topic 17)
A carboxylic acid is reduced to a primary alcohol only by the stronger reagent LiAlH4 in dry ether. Four [H] are needed (compare two for an aldehyde), and the second oxygen atom leaves as water.

A carboxylic acid is reduced to a primary alcohol by LiAlH4 in dry ether at room temperature. LiAlH4 reacts violently with water, so the ether must be dry.

CH3COOH + 4[H] → CH3CH2OH + H2O

CH3CH2COOH + 4[H] → CH3CH2CH2OH + H2O

Compare the aldehyde, which needs only 2[H] (Topic 17). NaBH4 is too weak to reduce a carboxylic acid, so aqueous NaBH4 leaves it unchanged. LiAlH4 reduces the C=O of the acid but does not reduce a C=C bond, so an alkene is left unchanged.

A typical sequence. Propanoic acid → (LiAlH4, dry ether) propan-1-ol → (concentrated H2SO4, heat; or passing the vapour over hot H3PO4) propene. The second step is the dehydration (elimination) of an alcohol from Topic 16.

⚠️ Examiner Trap: LiAlH4, not NaBH4, and not in water. NaBH4 does not reduce a carboxylic acid. Name LiAlH4 and say dry ether. The organic product is a primary alcohol with the same number of carbon atoms (the aldehyde is not isolated).

5. Esters and Esterification

carboxylic acidDiagram showing: carboxylic acid; CH3​COOH; ethanoic acid; +; alcohol; CH3​CH2​OH; ethanol; conc. H2​SO4​; ⇌; heat, reflux; ester + water; CH3​COOCH2​CH3​ + H2​O; ethyl ethanoate; Reading an ester name: the alcohol gives the first word, the acid gives the second. carboxylic acid CH3​COOH ethanoic acid + alcohol CH3​CH2​OH ethanol conc. H2​SO4​ ⇌ heat, reflux ester + water CH3​COOCH2​CH3​ + H2​O ethyl ethanoate Reading an ester name: the alcohol gives the first word, the acid gives the second. RCOOR′ from the ACID: -oate (ethanoic acid → ethanoate) ethyl ethanoate from the ALCOHOL: alkyl (ethanol → ethyl) ethanol + propanoic acid → ethyl propanoate (not propyl ethanoate) Condensation reaction: water is lost. Reversible, so an equilibrium mixture forms. Concentrated H2​SO4​ is the catalyst. Heat under reflux. Esters smell sweet and fruity. Raise the yield: use an excess of one reactant, or distil the ester off as it forms.
Esterification: a carboxylic acid and an alcohol, heated under reflux with concentrated H2SO4, form an ester and water in a reversible reaction. In the name, the part from the alcohol (alkyl) comes first and the part from the acid (-oate) comes second.

An ester contains the group –COO– between two carbon chains, RCOOR′. It is made by heating a carboxylic acid with an alcohol under reflux with a few drops of concentrated sulfuric acid as catalyst:

CH3COOH + CH3CH2OH ⇌ CH3COOCH2CH3 + H2O

This is a condensation reaction (a small molecule, water, is lost when two molecules join) and it is reversible, so the product is an equilibrium mixture of acid, alcohol, ester and water. The yield is raised by using an excess of one reactant (usually the cheaper one) or by distilling off the ester as it forms. Esters have sweet, fruity smells and are used as flavourings, perfumes and solvents. They have lower boiling points than carboxylic acids of similar Mr because they have no O–H group and so cannot form hydrogen bonds with each other.

Naming an ester. The first word comes from the alcohol (alkyl) and the second word comes from the acid (-oate).

Acid Alcohol Ester
ethanoic acid ethanol ethyl ethanoate, CH3COOCH2CH3
propanoic acid ethanol ethyl propanoate, CH3CH2COOCH2CH3
propanoic acid methanol methyl propanoate, CH3CH2COOCH3
ethanoic acid butan-1-ol butyl ethanoate, CH3COOCH2CH2CH2CH3

When you write the formula, write the acid part first: CH3CH2COOCH3 is methyl propanoate (the acid has three carbons, the alcohol has one), whereas CH3COOCH2CH3 is ethyl ethanoate.

⚠️ Examiner Trap: Which part is which? In the formula RCOOR′ the group on the carbonyl side comes from the acid and sets the second word; the group on the oxygen side comes from the alcohol and sets the first word. Ethanol and propanoic acid give ethyl propanoate, not propyl ethanoate. Esterification needs concentrated H2SO4 and reflux; the hydrolysis that reverses it uses dilute acid.

6. Hydrolysis of Esters

ACID HYDROLYSISDiagram showing: ACID HYDROLYSIS; reagent:; dilute H2​SO4​ or HCl; conditions:; heat under reflux; CH3​COOCH2​CH3​ + H2​O; ⇌ CH3​COOH + CH3​CH2​OH; REVERSIBLE; equilibrium mixture of ester, water,; carboxylic acid and alcohol; (the reverse of esterification); not all… ACID HYDROLYSIS reagent: dilute H2​SO4​ or HCl conditions: heat under reflux CH3​COOCH2​CH3​ + H2​O ⇌ CH3​COOH + CH3​CH2​OH REVERSIBLE equilibrium mixture of ester, water, carboxylic acid and alcohol (the reverse of esterification) not all the ester is used up ALKALI HYDROLYSIS reagent: dilute NaOH(aq) conditions: heat under reflux CH3​COOCH2​CH3​ + NaOH → CH3​COONa + CH3​CH2​OH GOES TO COMPLETION products: the SALT and the alcohol not reversible: the carboxylate ion does not react with the alcohol add dilute acid to get the free acid Release the acid: CH3​COONa + HCl → CH3​COOH + NaCl Either method splits the ester at the C–O bond: the acid part and the alcohol part separate.
Hydrolysis of an ester by dilute acid or by dilute alkali, both with heat under reflux. Acid hydrolysis is an equilibrium and leaves a mixture. Alkali hydrolysis is complete and gives the salt of the acid together with the alcohol.

Hydrolysis splits an ester back into its acid part and alcohol part. Both methods use heat under reflux.

Dilute acid (H2SO4 or HCl) Dilute alkali (NaOH(aq))
Equation (ethyl ethanoate) CH3COOCH2CH3 + H2O ⇌ CH3COOH + CH3CH2OH CH3COOCH2CH3 + NaOH → CH3COONa + CH3CH2OH
Extent reversible: an equilibrium mixture goes to completion
Organic products carboxylic acid and alcohol sodium carboxylate (salt) and alcohol

Why the difference? Acid hydrolysis is simply esterification run in reverse, so it reaches an equilibrium and some ester always remains. In alkali the acid is removed as its carboxylate ion, CH3COO−, which does not react with the alcohol, so the reaction cannot go backwards and all the ester can be hydrolysed (if there is enough alkali). To obtain the free acid after alkali hydrolysis, add dilute HCl or H2SO4: CH3COONa + HCl → CH3COOH + NaCl.

Worked example. Ethyl butanoate is heated under reflux with excess dilute NaOH(aq). CH3CH2CH2COOCH2CH3 + NaOH → CH3CH2CH2COONa + CH3CH2OH. The organic products are sodium butanoate and ethanol. The sodium salt comes from the acid part of the name (butanoate) and the alcohol from the first word (ethyl).

Worked example (identifying an ester). Compound X contains a single ester group and 27.6% oxygen by mass. Which pair of products could come from its hydrolysis: butan-1-ol and ethanoic acid, ethanol and propanoic acid, methanol and methanoic acid, or propan-2-ol and butanoic acid? One ester group contains two oxygen atoms (2 × 16.0 = 32.0), so Mr = 32.0 / 0.276 = 116 (Ar values from the Data Booklet). The formula is C6H12O2 (6 × 12.0 + 12 × 1.0 + 2 × 16.0 = 116). The acid and alcohol must together supply six carbon atoms in the ester, and the pair that adds up to six carbons is butan-1-ol (4) and ethanoic acid (2). Ethanol and propanoic acid give five carbons, and propan-2-ol with butanoic acid gives seven.

⚠️ Examiner Trap: Salt or acid? After heating with NaOH(aq) the organic product is the sodium salt, CH3COONa, not ethanoic acid. After heating with dilute acid you have an equilibrium mixture, not complete conversion. State the conditions as ‘dilute’ and ‘heat under reflux’, and use ⇌ for the acid hydrolysis and → for the alkali hydrolysis.

7. Distinguishing Compounds and Linking Routes

TestDiagram showing: Test; ethanoic acid; ethanol; ethyl ethanoate; Na2​CO3​(aq); effervescence,; CO2​ given off; no reaction; no reaction; acidified K2​Cr2​O7​; warm; stays orange; orange to green; stays orange Test ethanoic acid ethanol ethyl ethanoate Na2​CO3​(aq) effervescence, CO2​ given off no reaction no reaction acidified K2​Cr2​O7​ warm stays orange orange to green stays orange alkaline aqueous I2​ warm no precipitate yellow precipitate of CHI3​ no precipitate 2,4-DNPH no precipitate no precipitate no precipitate Na2​CO3​ picks out the acid. Dichromate and alkaline iodine pick out ethanol (CH3​CH2​OH). Acids and esters contain C=O but give no 2,4-DNPH precipitate (only aldehydes and ketones do).
Telling an acid, an alcohol and an ester apart. Aqueous sodium carbonate is the test for the acid; the oxidising and iodine tests recognise the alcohol; the ester gives no result with any of the four. Always state the result for every compound.
Compound Na2CO3(aq) Acidified K2Cr2O7, warm 2,4-DNPH
carboxylic acid fizzes (CO2) stays orange no ppt
primary alcohol no reaction orange to green no ppt
ester no reaction stays orange no ppt
aldehyde no reaction orange to green orange ppt

An ester can be recognised by its fruity smell, and by hydrolysis with hot NaOH(aq) followed by identification of the products: the acid from the salt by adding acid and testing with Na2CO3, and the alcohol by distillation and the dichromate or iodine tests.

carboxylicDiagram showing: carboxylic; acid; RCOOH; primary alcohol/aldehyde; RCH2​OH RCHO; excess K2​Cr2​O7​/H+​; reflux; nitrile; R–C≡N; dil. acid or alkali,; reflux; ester; RCOOR′; dil. acid or alkali, carboxylic acid RCOOH primary alcohol/aldehyde RCH2​OH RCHO excess K2​Cr2​O7​/H+​ reflux nitrile R–C≡N dil. acid or alkali, reflux ester RCOOR′ dil. acid or alkali, reflux ester RCOOR′ R′OH, conc. H2​SO4​ reflux carboxylate salt RCOO−​ M+​ metal, alkali, or carbonate primary alcohol RCH2​OH LiAlH4​, dry ether
Routes into and out of a carboxylic acid. On the left, three ways to make it; on the right, three reactions of it. The ester appears on both sides because esterification and acid hydrolysis are the same reaction in opposite directions.

Linking reactions into routes. For example, bromoethane to methyl propanoate:

Step Reagents and conditions Product
1 KCN in ethanol, heat under reflux propanenitrile
2 dilute HCl (or H2SO4), heat under reflux propanoic acid
3 methanol, a few drops of concentrated H2SO4, heat under reflux methyl propanoate

And ethanol to ethyl ethanoate: oxidise with excess acidified K2Cr2O7 under reflux to ethanoic acid, then heat the acid with more ethanol and concentrated H2SO4. Always give the reagent, the conditions and the intermediate for each step (Topic 21 builds on this).

Worked deduction. An ester W (Mr = 102.0) is hydrolysed by hot dilute NaOH to give a salt of a two-carbon acid and an alcohol X, which gives a yellow precipitate with alkaline aqueous iodine. The ester has formula C5H10O2 (5 × 12.0 + 10 × 1.0 + 2 × 16.0 = 102.0). The acid is ethanoic acid (2 carbons), so X has 3 carbons. X gives the iodine test, so it contains CH3CH(OH)–: X is propan-2-ol and W is propan-2-yl ethanoate, CH3COOCH(CH3)2.

8. Quick Sheet and Checklist

Topic Key point
Naming alkane − e + -oic acid; salt -oate; ester alkyl (alcohol) + -oate (acid)
Weak acid partial ionisation, ⇌; Ka(ethanoic acid) = 1.7 × 10−5 mol dm−3
Making 1° alcohol or aldehyde, excess K2Cr2O7/H+, reflux; nitrile + dilute acid, reflux; ester hydrolysis
With metal salt + H2 (2 mol RCOOH per mol H2)
With alkali salt + H2O
With carbonate salt + H2O + CO2 (fizz, limewater milky)
Reduction LiAlH4, dry ether: RCOOH + 4[H] → RCH2OH + H2O; NaBH4 does not work
Esterification acid + alcohol, conc. H2SO4, reflux; reversible; ester + water
Acid hydrolysis dilute acid, reflux; reversible; acid + alcohol
Alkali hydrolysis dilute NaOH, reflux; complete; salt + alcohol; acidify to get the acid
Gas volumes 24.0 dm3 mol−1 at room conditions; 22.4 dm3 mol−1 at s.t.p. (Data Booklet)

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