AS Organic Chemistry - Reactions red / orange ppt.

2,4-DNPH
r.t.: room temperature 2,4-dinitrophenylhydrazine
Δ: ̄̄heat ̄̄/ ̄̄reflux
[O] agent: KMnO4/dil. H2SO4 or K2Cr2O7/H2SO4
Addition
[H] agent: LiAlH4 in dry ether or NaBH4 in dry ether or H2/Pt or H2/Ni, heat
elimination
2,4-DNPH
CO2 + H2O or warm
CO2 + -CO2H or 3° ALCOHOL no oxidation
-CO2H + -CO2H or CH3COCl
CO2 + -CO- or 2° ALCOHOL [O], Δ KETONE
CH OHCH OH OH O red / orange ppt.
-CO2H + -CO- 2 2
| ║
Addition [H] Addition CH3COO ̄̄ ̄̄Na+
CO2 + H2O [EA] cold CH 3CHCH 3 CH 3CHCH3
polymerisation elimination or + H2 Substitution
and dilute Condensation SOCl2 or [Hyd]
KMnO4 2,4-DNPH
Redox C2H5O ̄̄ ̄̄Na+ + ½H2 Acid-base PCl3 or H2O
Complete warm
Na Na HCl PCl5
combustion Cracking [EA] or Hydration
O2 r.t.
Al2O3 or SiO2 H3PO4 or H2O [O]
450°C 300°C 60 atm distilled off [O], Δ
ALKANE ALKENE 1° ALCOHOL ALDEHYDE CARBOXYLIC ACID
CH3CH3 CH2═CH2 CH3CH2OH CH3CHO CH3COOH
[EA] or Reduction Dehydration or [E] [H], Δ [H], Δ
[FRS] or Hydrogenation conc. H2SO4, 180°C Substitution
Cl2 Tollen’s Base
UV light H2/Ni or H2/Pt or Al2O3, Δ HCl or Fehling’s KOH
[NS] reagent
150-170°C SOCl2, r.t. or solution r.t.
NaOH (aq) Ag(NH3)2+ Base
[EA] PCl3, Δ or warm
CH3CH2Cl Δ CH3COO ̄̄ ̄̄K+ CaCO3
[EA] HCl PCl5, r.t. r.t.
+ H2O
Br2 in CCl4 Ag + CH3COO ̄̄
dark HALOGENO-
[E] ALKANE silver ppt. Cu2O + CH3COO ̄̄
KOH/ethanol [NA] red ppt.
CH2BrCH2Br [EA] CH3CH2Cl HCN +
Br2 (aq) Δ
colourless NaCN (trace)
r.t. Esterification
[NS] [NS] 10-26°C CH3CH2OH (CH3COO ̄̄ ̄̄) 2Ca2+
KCN in ethanol NH3 conc. H2SO4
CH2BrCH2Br Δ + CO2 + H2O
Δ Δ
[E] Elimination + CH2BrCH2OH
[Hyd] Hydrolysis
[O] Oxidation [H] ESTER
NITRILE CH3CH2CN AMINE
[H] Reduction CH3COOCH2CH3
CH3CH2NH2 [Hyd]
[FRS] Free radical substitution [Hyd] dil. HCl or
[EA] Electrophilic addition dil. HCl or H2SO4 [Hyd] [Hyd]
H2SO4 [H] NaOH (aq)
[ES] Electrophilic substitution Δ dil. H +
[NA] Nucleophilic addition Δ Δ
[NS] Nucleophilic substitution
[AB] Acid-base reaction CH3CH2COOH AMINE CH3COO ̄̄ ̄̄Na+ CH3COOH
CH3CH2CH2NH2 + CH3CH2OH + CH3CH2OH
 NH2
A2 Important Organic OH Ō Na+ Neutralisation
Cl Br Br NaOH, r.t
Reactions Redox
[ES] purple
[ES] Na, r.t. colouration
Cl2/FeCl3
ARYL Br2
or Cl2/AlCl3
HALIDE r.t. Br
or Cl2/Fe
[ES] Diazotisation +N≡N
Br dark, r.t. NO2 NH2 Cl ̄ OH OH
conc. H2SO4/ [H] NaNO3 + HCl or
conc. HNO3 Sn/conc. HCl NaNO3 + HNO2 Substitution 2ON NO2
50-60°C Reflux 0-5°C H2O, warm

[ES] benzene [ES]

Br2/FeBr3 conc. HNO3
or Br2/AlBr3 ARENE COO ̄̄ ̄̄Na + PHENYL- diazonium PHENOL r.t.
dark, r.t. AMINE NO2
[ES]
CH3 CH3Cl or AlCl3
Coupling
or FeCl3
[ES]
NO2 dark, r.t. [AB] + OH Ba2 (aq) [ES]
Na2CO3, r.t. r.t.
[ES] COOH N dil. HNO3
CH3 COCl NaOH, <5°C
conc. H2SO4 [O] ║ r.t.
[Hyd]
conc. HNO3 KMnO4/H+
+ 30°C Δ
H2O N
OH
CH3
Substitution OCOCH3 Br Br
methyl SOCl2 or PCl3
or PCl5
ACYL
benzene CHLORIDE
[ES] [Hyd] r.t. OH
[FRS] NaOH (aq), Δ
Cl3 or OH
FeCl3
Cl2, UV Br NO2
NO2
or AlCl3 No reaction with
CH2Cl CHCl2 CCl3

Condensation / [NS]
OH SOCl2 or PCl5
CH3
excess Cl2 excess Cl2 O ESTER
UV UV r.t. +
Cl ║
OH
C–O
Triiodomethane Test
[Hyd] [Hyd] NH3 O
+ NaOH (aq), Δ NaOH (aq), Δ OH ║ AMIDE O OH
CH3 | C–NH2 ║ and |
CH2OH CHO H – C – CN CH3–C CH3–C–
[H] [NS] RNH2 O | NO2
LiAlH4 HCN/NaOH H
║ show positive
in dry ether 10-20°C
C–N–R result (yellow ppt.)
| with I2/NaOH(aq)
Cl H