Chemistry · Organic Chemistry

Aldehydes Ketones and Carboxylic Acids formulas for JEE

Every Aldehydes Ketones and Carboxylic Acids formula you need for JEE, grouped by concept.

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32 formulas6 concepts
01Aldehydes and Ketones02Aldehyde and Ketone Properties03Important Reactions of Aldehydes and Ketones04Carboxylic Acids05Carboxylic Properties06Carboxylic Reactions
01

Aldehydes and Ketones

8 formulas

Acetal Formation

R−CHO+2R′OH⇌dry HClR−CH(OR′)2+H2OR-CHO + 2R'OH \xrightleftharpoons{\text{dry } HCl} R-CH(OR')_2 + H_2O

Reaction of aldehydes with two equivalents of monohydric alcohol in the presence of dry HCl.

applies whenReversible reaction; water must be removed to drive equilibrium.
acetalhemiacetalnucleophilic_addition

Cyanohydrin Formation

>C=O+HCN→OH−>C(OH)(CN)>C=O + HCN \xrightarrow{OH^-} >C(OH)(CN)

Base-catalyzed nucleophilic addition of HCN to carbonyl compounds.

applies whenRequires base catalyst to generate sufficient CN- nucleophile.
cyanohydrinnucleophilic_addition

Ketone Synthesis via Dialkylcadmium

2R−COCl+R2′Cd→2R−CO−R′+CdCl22R-COCl + R'_2Cd \rightarrow 2R-CO-R' + CdCl_2

Preparation of ketones from acyl chlorides using dialkylcadmium.

applies whenAvoids over-reaction to tertiary alcohols (unlike direct Grignard reagent usage).
ketonedialkylcadmiumacyl_chloride

Etard Reaction

Ar−CH3+2CrO2Cl2→CS2Chromium Complex→H3O+Ar−CHOAr-CH_3 + 2CrO_2Cl_2 \xrightarrow{CS_2} \text{Chromium Complex} \xrightarrow{H_3O^+} Ar-CHO

Oxidation of toluene to benzaldehyde using chromyl chloride.

applies whenSpecific for preparing aromatic aldehydes from methylbenzenes.
etardoxidationbenzaldehyde

Gatterman-Koch Reaction

C6H6+CO+HCl→Anhyd. AlCl3/CuClC6H5CHOC_6H_6 + CO + HCl \xrightarrow{\text{Anhyd. } AlCl_3/CuCl} C_6H_5CHO

Formylation of benzene or its derivatives using CO and HCl.

applies whenRequires anhydrous AlCl3 and CuCl as catalysts.
gatterman_kochformylationbenzaldehyde

Addition of Ammonia Derivatives

>C=O+H2N−Z⇌H+>C=N−Z+H2O>C=O + H_2N-Z \xrightleftharpoons{H^+} >C=N-Z + H_2O

Acid-catalyzed reversible condensation of carbonyls with ammonia derivatives.

applies whenpH strictly controlled (weakly acidic) to maximize product.
iminehydrazoneoximecondensation

Rosenmund Reduction

R−COCl+H2→Pd/BaSO4R−CHO+HClR-COCl + H_2 \xrightarrow{Pd/BaSO_4} R-CHO + HCl

Hydrogenation of acyl chloride to aldehyde over a poisoned palladium catalyst.

applies whenApplicable for aldehydes only; ketones cannot be prepared.
rosenmundreductionaldehydeacyl_chloride

Stephen Reaction

R−CN+SnCl2+HCl→R−CH=NH→H3O+R−CHOR-CN + SnCl_2 + HCl \rightarrow R-CH=NH \xrightarrow{H_3O^+} R-CHO

Reduction of nitriles to imines using stannous chloride and HCl, followed by hydrolysis to aldehydes.

applies whenSelective for nitriles to aldehydes.
stephenreductionaldehydenitrile
02

Aldehyde and Ketone Properties

1 formula

Boiling Point Trend

Tbp(Alkane)<Tbp(Ether)<Tbp(Aldehyde/Ketone)<Tbp(Alcohol)T_{bp}(\text{Alkane}) < T_{bp}(\text{Ether}) < T_{bp}(\text{Aldehyde/Ketone}) < T_{bp}(\text{Alcohol})

General order of boiling points for compounds of comparable molecular mass.

applies whenAssuming comparable molecular mass.
boiling_pointintermolecular_forces
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03

Important Reactions of Aldehydes and Ketones

13 formulas

Aldol Condensation

2R−CH2−CHO→dil. NaOHR−CH2−CH(OH)−CH(R)−CHO→Δ,−H2OR−CH2−CH=C(R)−CHO2 R-CH_2-CHO \xrightarrow{\text{dil. } NaOH} R-CH_2-CH(OH)-CH(R)-CHO \xrightarrow{\Delta, -H_2O} R-CH_2-CH=C(R)-CHO

Base-catalyzed condensation of aldehydes or ketones containing alpha-hydrogen to form alpha,beta-unsaturated carbonyls.

applies whenRequires at least one alpha-hydrogen.
aldolcondensationalpha_hydrogen

Cannizzaro Reaction

2HCHO→conc. KOHCH3OH+HCOO−K+2 HCHO \xrightarrow{\text{conc. } KOH} CH_3OH + HCOO^- K^+

Disproportionation of aldehydes lacking alpha-hydrogens in concentrated alkali to form an alcohol and a carboxylate salt.

applies whenRequires absence of alpha-hydrogens.
cannizzarodisproportionationredox

Haloform Reaction

R−CO−CH3+3NaOX→R−COONa+CHX3↓+2NaOHR-CO-CH_3 + 3NaOX \rightarrow R-COONa + CHX_3\downarrow + 2NaOH

Oxidation of methyl ketones by sodium hypohalite to yield haloform and a carboxylate salt.

applies whenRequires a methyl group directly attached to the carbonyl carbon (or secondary methyl carbinol).
haloformiodoformmethyl_ketone

Baeyer-Villiger Oxidation

R−CO−R′+R′′−CO3H→R−CO−OR′+R′′−COOHR-CO-R' + R''-CO_3H \rightarrow R-CO-OR' + R''-COOH

Oxidation of a ketone to an ester using peroxyacids.

applies whenMigratory aptitude determines the primary ester product (Tertiary > Secondary > Primary > Methyl).
baeyer_villigeroxidationjee-advanced

Beckmann Rearrangement

R−C(=N−OH)−R′→H+ or PCl5R−CO−NH−R′R-C(=N-OH)-R' \xrightarrow{H^+\text{ or }PCl_5} R-CO-NH-R'

Acid-catalyzed rearrangement of an oxime to an amide.

applies whenStrict anti-migration: group anti to the hydroxyl group migrates to nitrogen.
beckmannrearrangementjee-advanced

Benzoin Condensation

2ArCHO→KCN / EtOH, ΔAr−CH(OH)−CO−Ar2 ArCHO \xrightarrow{KCN\text{ / }EtOH,\ \Delta} Ar-CH(OH)-CO-Ar

Condensation of two molecules of aromatic aldehydes using cyanide ion as catalyst.

applies whenCatalyzed uniquely by cyanide ions.
benzoincondensationjee-advanced

Clemmensen Reduction

>C=O+4[H]→Zn−Hg, conc. HCl>CH2+H2O>C=O + 4[H] \xrightarrow{Zn-Hg,\ \text{conc. } HCl} >CH_2 + H_2O

Reduction of carbonyl group to methylene group using zinc amalgam and concentrated HCl.

applies whenNot suitable for acid-sensitive compounds.
clemmensenreductionalkane

Fehling's Test

R−CHO+2Cu2++5OH−→ΔR−COO−+Cu2O↓+3H2OR-CHO + 2Cu^{2+} + 5OH^- \xrightarrow{\Delta} R-COO^- + Cu_2O\downarrow + 3H_2O

Oxidation of aliphatic aldehydes by Cu2+ in alkaline tartrate solution to form red cuprous oxide precipitate.

applies whenAromatic aldehydes and ketones do not respond.
fehlingoxidationred_ppt

Perkin Reaction

ArCHO+(R−CH2−CO)2O→R−CH2−COONa, ΔAr−CH=C(R)−COOH+R−CH2−COOHArCHO + (R-CH_2-CO)_2O \xrightarrow{R-CH_2-COONa,\ \Delta} Ar-CH=C(R)-COOH + R-CH_2-COOH

Condensation of an aromatic aldehyde and an acid anhydride to yield alpha,beta-unsaturated aromatic acid.

applies whenSodium salt of acid must correspond to the anhydride used.
perkincondensationjee-advanced

Reformatsky Reaction

>C=O+Br−CH2−COOC2H5→1. Zn, 2. H3O+>C(OH)−CH2−COOC2H5>C=O + Br-CH_2-COOC_2H_5 \xrightarrow{\text{1. }Zn\text{, 2. }H_3O^+} >C(OH)-CH_2-COOC_2H_5

Condensation of aldehydes/ketones with alpha-halo esters using zinc to form beta-hydroxy esters.

applies whenZinc is used because it is less reactive than Grignard, avoiding reaction with ester groups.
reformatskyzincjee-advanced

Tischenko Reaction

2R−CHO→Al(OC2H5)3R−COOCH2R2 R-CHO \xrightarrow{Al(OC_2H_5)_3} R-COOCH_2R

Modified Cannizzaro-type disproportionation forming esters directly from aldehydes.

applies whenWorks on both enolizable and non-enolizable aldehydes.
tischenkoesterificationjee-advanced

Tollens' Test

R−CHO+2[Ag(NH3)2]++3OH−→ΔR−COO−+2Ag↓+4NH3+2H2OR-CHO + 2[Ag(NH_3)_2]^+ + 3OH^- \xrightarrow{\Delta} R-COO^- + 2Ag\downarrow + 4NH_3 + 2H_2O

Oxidation of aldehydes by ammoniacal silver nitrate to form a silver mirror.

applies whenSpecific to aldehydes; ketones do not react.
tollensoxidationsilver_mirror

Wolff-Kishner Reduction

>C=O+NH2NH2→−H2O>C=NNH2→KOH/ethylene glycol, Δ>CH2+N2>C=O + NH_2NH_2 \xrightarrow{-H_2O} >C=NNH_2 \xrightarrow{KOH\text{/ethylene glycol, } \Delta} >CH_2 + N_2

Reduction of carbonyl group to methylene group via hydrazone intermediate under strongly basic conditions.

applies whenNot suitable for base-sensitive compounds.
wolff_kishnerreductionalkane
04

Carboxylic Acids

3 formulas

Oxidation of Alkylbenzenes

Ar−CH2−R→1. KMnO4/KOH, Δ 2. H3O+Ar−COOHAr-CH_2-R \xrightarrow{\text{1. } KMnO_4/KOH,\ \Delta\text{ 2. } H_3O^+} Ar-COOH

Vigorous oxidation of primary or secondary alkyl side chains on benzene rings to form benzoic acid.

applies whenRequires at least one benzylic hydrogen; tertiary alkyls do not react.
alkylbenzeneoxidationbenzoic_acid

Carboxylic Acid from Grignard

R−MgX+CO2→R−COOMgX→H3O+R−COOHR-MgX + CO_2 \rightarrow R-COOMgX \xrightarrow{H_3O^+} R-COOH

Synthesis of carboxylic acids by reacting Grignard reagents with carbon dioxide (dry ice).

applies whenAscends the series by adding one carbon atom.
grignardcarboxylationdry_ice

Nitrile Hydrolysis

R−CN→H+ or OH−, H2OR−CONH2→Δ, H+ or OH−R−COOHR-CN \xrightarrow{H^+\text{ or }OH^-,\ H_2O} R-CONH_2 \xrightarrow{\Delta,\ H^+\text{ or }OH^-} R-COOH

Acid or base catalyzed hydrolysis of nitriles via amide intermediate to yield carboxylic acids.

applies whenMild conditions stop at amide; vigorous heating yields the acid.
nitrilehydrolysisamide
05

Carboxylic Properties

2 formulas

Carboxylic Acidity Substituent Effect

−CF3>−NO2>−CN>−F>−Cl>−Br>−I>−Ph-CF_3 > -NO_2 > -CN > -F > -Cl > -Br > -I > -Ph

Effect of electron withdrawing groups on increasing carboxylic acid strength via -I effect.

acidity_trendinductive_effectewg

Acid Dissociation pKa

pKa=−log⁡10KapK_a = -\log_{10} K_a

Logarithmic measure of acid dissociation constant used to compare carboxylic acid strength.

applies whenSmaller pKa indicates stronger acid.
pkaaciditydissociation
06

Carboxylic Reactions

5 formulas

Decarboxylation

R−COONa→ΔNaOH, CaOR−H+Na2CO3R-COONa \xrightarrow[\Delta]{NaOH,\ CaO} R-H + Na_2CO_3

Loss of carbon dioxide from sodium carboxylates heated with sodalime to form hydrocarbons.

applies whenRatio of NaOH to CaO is 3:1.
decarboxylationsodalimehydrocarbon

Esterification

R−COOH+R′OH⇌H+R−COOR′+H2OR-COOH + R'OH \xrightleftharpoons{H^+} R-COOR' + H_2O

Acid-catalyzed condensation of a carboxylic acid with an alcohol to form an ester.

applies whenReversible; continuous water removal shifts equilibrium right.
esterificationreversiblecondensation

Hell-Volhard-Zelinsky (HVZ) Reaction

R−CH2−COOH→1. X2/Red P, 2. H2OR−CH(X)−COOHR-CH_2-COOH \xrightarrow{\text{1. } X_2/\text{Red } P,\ \text{2. } H_2O} R-CH(X)-COOH

Alpha-halogenation of carboxylic acids using chlorine or bromine with red phosphorus.

applies whenRequires at least one alpha-hydrogen.
hvzhalogenationalpha_halo

Kolbe Electrolysis

2R−COONa+2H2O→ElectrolysisR−R+2CO2+H2+2NaOH2R-COONa + 2H_2O \xrightarrow{\text{Electrolysis}} R-R + 2CO_2 + H_2 + 2NaOH

Electrolysis of aqueous alkali metal carboxylate yielding symmetric alkanes.

applies whenForms symmetric alkanes; methane cannot be prepared.
kolbeelectrolysisalkane

Acyl Chloride Formation

R−COOH+SOCl2→R−COCl+SO2↑+HCl↑R-COOH + SOCl_2 \rightarrow R-COCl + SO_2\uparrow + HCl\uparrow

Conversion of carboxylic acids to acyl chlorides using thionyl chloride.

applies whenPreferred method as byproducts are volatile gases.
thionyl_chlorideacyl_chloride
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