Organic Conversion Ladder - Full Guide
By Raghav Kashyap
1. UPWARD LADDER (Build-up / Functionalization)
Alkane -> (Cl2 / hv) -> Alkyl halide
Alkyl halide -> (KOH, aq) -> Alcohol
Alcohol -> (PCC) -> Aldehyde (primary) / (K2Cr2O7) -> Ketone (secondary)
Aldehyde -> (KMnO4 / K2Cr2O7) -> Carboxylic acid
Alcohol -> (KMnO4 / K2Cr2O7) -> Carboxylic acid (complete oxidation)
Carboxylic acid -> (SOCl2 / PCl5) -> Acid chloride
Acid chloride -> (NH3 / RNH2) -> Amide
Acid chloride -> (ROH) -> Ester
Ester -> (acidic or basic hydrolysis) -> Carboxylic acid + Alcohol
Nitrile -> (H3O+ / heat) -> Carboxylic acid
Nitrile -> (LiAlH4 or H2 / catalyst) -> Amine
2. DOWNWARD LADDER (Reduction / Simplification)
Acid chloride -> (Rosenmund: H2 / Pd-BaSO4) -> Aldehyde
Aldehyde / Ketone -> (NaBH4 or LiAlH4) -> Alcohol
Aldehyde / Ketone -> (Wolff-Kishner: NH2NH2 / KOH or Clemmensen: Zn-Hg / HCl) -> Alkane
Carboxylic acid -> (LiAlH4) -> Primary alcohol
Amide -> (LiAlH4) -> Amine
Nitrobenzene -> (Sn/HCl or Fe/HCl or H2/Pd) -> Aniline (C6H5NH2)
Alkene -> (H2 / Ni or Pt) -> Alkane
Alkyne -> (H2 / Lindlar) -> cis-Alkene or (Na / NH3) -> trans-Alkene
3. IMPORTANT BENZENE DERIVATIVES (Structures & Notes)
Benzene : C6H6 - Aromatic ring
Toluene : C6H5CH3 - Methylbenzene
Benzyl alcohol : C6H5CH2OH - Benzylic primary alcohol (benzyl-)
Benzaldehyde : C6H5CHO - Aromatic aldehyde (benzal- / benzalde-)
Benzoic acid : C6H5COOH - Aromatic carboxylic acid (benzoic-)
Benzoyl chloride : C6H5COCl - Acid chloride (benzoyl-)
Benzamide : C6H5CONH2 - Amide from benzoic acid
Benzophenone : C6H5COC6H5 - Diaryl ketone
Acetophenone : C6H5COCH3 - Aryl methyl ketone (phenyl-)
Nitrobenzene : C6H5NO2 - Nitro group (precursor to aniline)
Aniline : C6H5NH2 - Aromatic amine (from nitro reduction)
Benzyl chloride : C6H5CH2Cl - Benzylic halide
Benzyl cyanide : C6H5CH2CN - Benzylic nitrile
4. KEY REAGENTS (Quick Reference)
NaBH4 : Mild reducing agent - reduces aldehydes/ketones to alcohols
LiAlH4 : Strong reducing agent - reduces acids, esters, amides, nitriles to
alcohols/amines
PCC : Mild oxidant - alcohol to aldehyde (no further to acid)
KMnO4 / K2Cr2O7 : Strong oxidants - alcohols -> acids, aldehydes -> acids
SOCl2 / PCl5 : Converts COOH -> COCl (acid chloride formation)
H2 / Pd-BaSO4 : Rosenmund - reduces acid chloride -> aldehyde
NH2NH2 / KOH : Wolff-Kishner - reduces ketone/aldehyde -> alkane (basic)
Zn-Hg / HCl : Clemmensen - reduces ketone/aldehyde -> alkane (acidic)
HCN : Adds CN to carbonyl -> cyanohydrin (use with care)
RMgX (Grignard) : Adds R- to carbonyl -> alcohol after workup
5. MNEMONICS & EXAM TRICKS
HACO : Halide -> Alcohol -> Carbonyl -> Oxidized (acid)
Oxidation : OH -> CHO -> COOH
Reduction : COOH -> CHO -> CH2OH -> CH3
Cannizzaro : Aldehyde without alpha-H + conc. NaOH -> one alcohol + one carboxylate
Aldol : Two carbonyls (with alpha-H) + base -> beta-hydroxy ->
alpha,beta-unsaturated
Choose Clemmensen (acid) or Wolff-Kishner (base) based on molecule stability
6. Visual Flowchart (Colored)