Alcohol & carbonyl interconversions template

Functional-group interconversion map: propan-1-ol ⇄ propanal → propanoic acid ⇄ methyl propanoate, propan-2-ol ⇄ propanone, acid → acid chloride → amide and ester, and LiAlH₄ reduction back to the alcohol, reagents on every arrow.

What the template shows

• Oxidation up, reduction down, and the acid-derivative ladder: the C₃ series with the reagent on each arrow
• Carboxylic acid
• Acid chloride
• Primary amide
• PCC, DMP or Swern
• NaBH₄, MeOH
• Jones or NaClO₂ (Pinnick)
• MeOH, H₂SO₄ (cat.), Δ
• NaOH, H₂O; then H₃O⁺
• PCC, DMP, Swern or Jones
• MeOH, pyridine
• LiAlH₄, Et₂O; then H₃O⁺ (esters and acids → 1° alcohol)
• Oxidation level rises left to right: 1° alcohol → aldehyde → carboxylic acid. Anhydrous oxidants (PCC, DMP, Swern) stop at the aldehyde; aqueous Jones reagent oxidises a 1° alcohol all the way to the acid.
• 2° alcohols oxidise only to ketones; 3° alcohols are not oxidised (no H on the carbinol carbon).
• NaBH₄ reduces aldehydes and ketones but not esters or acids; LiAlH₄ reduces esters and acids to 1° alcohols (DIBAL-H at −78 °C stops an ester at the aldehyde).
• Acid derivatives interconvert downhill in reactivity: acid chloride > anhydride > ester > amide. SOCl₂ activates the acid; the acid chloride then gives esters (ROH, pyridine) and amides (NH₃ or amines, 2 equiv).
• Fischer esterification is an equilibrium (excess alcohol or removal of water drives it); saponification with NaOH is irreversible because it forms the carboxylate.
• Every part of this figure is editable · sources on the template card

Drawn with 37 atoms, 44 shapes – every one editable in MolDraw.

Sources

• Clayden, Greeves & Warren, Organic Chemistry, 2nd ed., OUP 2012, ch. 23 Textbook
• Wade, Organic Chemistry, 8th ed., Pearson 2013 Textbook
• Smith, March's Advanced Organic Chemistry, 7th ed., Wiley 2013 Textbook