Concept Trees
Visualise complex reaction pathways and interconversions.
Showing 16 pathways
Reactions of a Haloalkane (R–X)
Haloalkanes & Haloarenes
Tap any product with a ▶ to see what it goes on to form. Colours mark the reaction type (see legend).
Haloalkane
R–X
aq. KOH / NaOHΔ
Alcohol
R–OH
PCC
Aldehyde (from 1°)
R–CHO
conc. H₂SO₄443 K
Alkene
C=C
alc. KOHΔ
Alkene
C=C
KCN (alcoholic)
Alkanenitrile
R–C≡N
LiAlH₄ / H₂-Ni
1° Amine
R–CH₂–NH₂
H₃O⁺ (hydrolysis)
Carboxylic acid
R–COOH
AgCN (alcoholic)
Alkyl isocyanide
R–N≡C
NH₃ (excess)
1° Amine
R–NH₂
R'–ONa (Williamson)
Ether
R–O–R'
AgNO₂
Nitroalkane
R–NO₂
Na, dry ether (Wurtz)
Alkane (higher)
R–R
Mg, dry ether
Grignard reagent
R–MgX
CO₂ then H₃O⁺
Carboxylic acid
R–COOH
HCHO then H₃O⁺
1° Alcohol
R–CH₂OH
H₂O
Alkane
R–H
NaI, acetone (Finkelstein)
Alkyl iodide
R–I
Reactions of an Alcohol (R–OH)
Alcohols, Phenols & Ethers
Oxidation climbs 1° → aldehyde → acid; dehydration gives alkenes/ethers. Tap ▶ nodes to go deeper.
Alcohol
R–OH
HX / Lucas (HCl·ZnCl₂)
Haloalkane
R–X
conc. H₂SO₄443 K
Alkene
C=C
conc. H₂SO₄413 K
Ether
R–O–R
PCC
Aldehyde
R–CHO
KMnO₄ / K₂Cr₂O₇
Carboxylic acid
R–COOH
K₂Cr₂O₇ / H⁺ (1°)
Carboxylic acid
R–COOH
[O] (2° alcohol)
Ketone
R–CO–R'
Na metal
Sodium alkoxide
R–ONa
R'COOH / conc. H₂SO₄
Ester
R'COOR
Reactions of Phenol (C₆H₅OH)
Alcohols, Phenols & Ethers
−OH strongly activates the ring (o/p) and is acidic. Tap ▶ on phenoxide for Kolbe & Reimer–Tiemann.
Phenol
C₆H₅OH
NaOH
Sodium phenoxide
C₆H₅ONa
CO₂, 400 K, 4–7 atm; H⁺
Salicylic acid
2-HO-C₆H₄-COOH
CHCl₃ + NaOH; H⁺
Salicylaldehyde
2-HO-C₆H₄-CHO
Br₂ (aq.)
2,4,6-Tribromophenol
C₆H₂Br₃OH
conc. HNO₃
Picric acid
2,4,6-(NO₂)₃C₆H₂OH
Zn dustΔ
Benzene
C₆H₆
(CH₃CO)₂O
Phenyl acetate
C₆H₅OOCCH₃
Fundamental Organic Reaction Types
General Organic Chemistry
Organic Substrate
Nu- (Nucleophile)
Substituted Product
E+ (Electrophile) + Nu-
Addition Product
Strong Base / Heat
Alkene / Alkyne
Free Radical Initiator (hv / peroxides)
Radical Substituted Product
Reactions of Ethene
Hydrocarbons
A comprehensive map of electrophilic addition, oxidation, and polymerization of alkenes.
Ethene (CH₂=CH₂)
C2H4
H₂ / Pd, Pt, or Ni
Ethane
CH₃-CH₃
Br₂ in CCl₄
1,2-Dibromoethane
CH₂Br-CH₂Br
HX (e.g., HBr)
Ethyl bromide
CH₃-CH₂Br
H₂O / H⁺
Ethanol
CH₃-CH₂OH
1. O₃ 2. Zn/H₂O
Formaldehyde (2 moles)
2 HCHO
Cold dil. KMnO₄ (Baeyer's reagent)
Ethane-1,2-diol (Ethylene glycol)
HO-CH₂-CH₂-OH
Electrophilic Aromatic Substitution
Hydrocarbons
Benzene
C6H6
Cl₂ / Anhydrous AlCl₃
Chlorobenzene
C₆H₅Cl
Conc. HNO₃ + Conc. H₂SO₄
Nitrobenzene
C₆H₅NO₂
CH₃Cl / Anhyd. AlCl₃
Toluene
C₆H₅CH₃
CH₃COCl / Anhyd. AlCl₃
Acetophenone
C₆H₅COCH₃
Preparation of Nitric Acid (Ostwald Process)
The p-Block Elements
Industrial manufacture of HNO₃.
Ammonia + Air
NH₃ + O₂
Pt/Rh gauge catalyst, 500K, 9 bar
Nitric Oxide
NO
O₂
Nitrogen Dioxide
2NO₂
Preparation of Sulphuric Acid (Contact Process)
The p-Block Elements
Industrial manufacture of H₂SO₄.
Sulphur / Sulphide Ore + Air
S + O₂
Burning
Sulphur Dioxide
SO₂
V₂O₅ catalyst, 720K, 2 bar
Sulphur Trioxide
SO₃
Oxidising Action of KMnO₄
The d- and f-Block Elements
Reactions of Permanganate (MnO₄⁻) in different media.
KMnO₄ (MnO₄⁻)
Mn(+7)
Acidic Medium (H⁺)
Manganese(II)
Mn²⁺
Fe²⁺ (Ferrous)
Fe³⁺ (Ferric)
Fe³⁺
I⁻ (Iodide)
I₂ (Iodine)
I₂
C₂O₄²⁻ (Oxalate)
CO₂ (Carbon dioxide)
CO₂
S²⁻ (Sulphide)
S (Sulphur)
S↓
Neutral / Faintly Alkaline Medium (H₂O or OH⁻)
Manganese Dioxide
MnO₂↓
I⁻ (Iodide)
IO₃⁻ (Iodate)
IO₃⁻
S₂O₃²⁻ (Thiosulphate)
SO₄²⁻ (Sulphate)
SO₄²⁻
Chemistry of K₂Cr₂O₇
The d- and f-Block Elements
Preparation, pH dependence, and oxidising action of Dichromate.
Chromite Ore
FeCr₂O₄
Na₂CO₃ + O₂ (Roasting)
Sodium Chromate (Yellow)
Na₂CrO₄
H⁺ (Acidification)
Sodium Dichromate (Orange)
Na₂Cr₂O₇
Extraction of Copper from Copper Pyrites
General Principles and Processes of Isolation of Elements
Steps involving roasting, smelting, and self-reduction.
Copper Pyrites
CuFeS₂
O₂ / Roasting
Roasted Ore
Cu₂S + FeS
Silica (SiO₂) + Blast of Air
Copper Matte
Cu₂S + FeS
Reactions of Carbonyl Group (>C=O)
Aldehydes, Ketones and Carboxylic Acids
A unified tree showing all major reaction classes of the carbonyl group.
Carbonyl Compound
>C=O
Nucleophilic Addition
Addition Products
Various
HCN
Cyanohydrin
>C(OH)CN
NaHSO₃
Bisulphite addition compound
>C(OH)SO₃Na
1. RMgX, 2. H₂O
Alcohol
>C(OH)R
Alcohol + dry HCl
Acetal / Ketal
>C(OR)₂
Reduction
Reduced Products
Various
NaBH₄ or LiAlH₄
Alcohol
>CH-OH
Zn-Hg, conc. HCl (Clemmensen)
Alkane
>CH₂
NH₂NH₂, KOH, glycol (Wolff-Kishner)
Alkane
>CH₂
Oxidation
Oxidized Products
Carboxylic Acids
KMnO₄ / K₂Cr₂O₇ / HNO₃
Carboxylic Acid
R-COOH
Tollens' reagent [Ag(NH₃)₂]⁺
Carboxylate + Ag mirror
R-COO⁻ + Ag↓
Fehling's solution
Carboxylate + Cu₂O
R-COO⁻ + Cu₂O↓ (Red)
Reactions due to α-Hydrogen
α-Substituted / Condensation Products
Various
Dil. NaOH (Aldol)
β-Hydroxy aldehyde (Aldol)
R-CH(OH)-CH(R')-CHO
Conc. KOH (Cannizzaro)
Alcohol + Carboxylate
R-CH₂OH + R-COO⁻
X₂ / Red P (HVZ - for acids)
α-Halo carboxylic acid
R-CH(X)-COOH
Reactions of Carboxylic Acids (Acid Derivatives)
Acid Derivatives
R-CO-Z
SOCl₂ / PCl₅ / PCl₃
Acid Chloride
R-COCl
R'OH, H⁺
Ester
R-COOR'
NH₃, Heat
Amide
R-CONH₂
P₂O₅, Heat
Acid Anhydride
(R-CO)₂O
Reactions of Aliphatic and Aromatic Amines
Amines
Chemical properties of R-NH₂ and Ar-NH₂.
Primary Amine
R-NH₂ or Ar-NH₂
Nitrous Acid (NaNO₂ + HCl)
Varies by Amine Type
Alcohol or Diazonium
Acid chloride / Anhydride
Amide
R-NH-CO-R'
CHCl₃ + KOH (Heat)
Isocyanide (Carbylamine)
R-NC
Benzenesulphonyl chloride (Hinsberg reagent)
Sulphonamide
Ph-SO₂-NH-R
Alkyl Halide (R-X)
Mixture of 2°, 3°, and quaternary salts
R₂NH, R₃N, R₄N⁺X⁻
Electrophilic Substitution (for Aniline)
Substituted Anilines
Various
Br₂ / H₂O
2,4,6-Tribromoaniline
White ppt
HNO₃ / H₂SO₄
Mixture of o, m, p-nitroanilines
Significant meta product (47%) due to anilinium ion formation.
Reactions of Benzenediazonium Chloride
Amines
Versatility of diazonium salts in synthesizing aryl compounds.
Benzenediazonium Chloride
C₆H₅N₂⁺Cl⁻
CuCl/HCl or CuBr/HBr or CuCN/KCN
Aryl Halide / Cyanide
Ar-Cl, Ar-Br, Ar-CN
Cu powder / HCl or HBr
Aryl Halide
Ar-Cl, Ar-Br
H₂O (Warm)
Phenol
Ar-OH
H₃PO₂ / H₂O or CH₃CH₂OH
Benzene
Ar-H
HBF₄, then heat
Fluorobenzene
Ar-F
KI
Iodobenzene
Ar-I
Phenol or Aniline (Coupling)
Azo Dye
Ar-N=N-Ar'
Major Polymerization Mechanisms
Polymers
Pathways for forming long chain polymers.
Monomers
Alkenes / Dienes or Bifunctional groups
Peroxide (Initiator), Heat/Light
Addition Polymer
Chain-growth polymer
Ethene
Polythene
[-CH₂-CH₂-]_n
Vinyl Chloride
Polyvinyl Chloride (PVC)
[-CH₂-CH(Cl)-]_n
Tetrafluoroethene
Teflon (PTFE)
[-CF₂-CF₂-]_n
Heat, High Pressure, Bifunctional monomers
Condensation Polymer
Step-growth polymer
Adipic Acid + Hexamethylenediamine
Nylon 6,6
Polyamide
Ethylene glycol + Terephthalic acid
Terylene (Dacron)
Polyester
Phenol + Formaldehyde
Bakelite
Cross-linked resin
Preparation of Soap (Saponification)
Chemistry in Everyday Life
Alkaline hydrolysis of fats/oils.
Fat / Oil (Triglyceride)
(R-COO)₃C₃H₅
Aqueous NaOH, Heat
Soap + Glycerol
3 R-COONa + C₃H₅(OH)₃