RO – H Cleavage:

Common Properties Esterification •

R’ = Cn’H2n’+1 and R = CnH2n+1 (Note: R and R’ might be the same).
(1°,2°& 3° alcohols) (athermic) •
Important:
→ → Reactivity of ROH: CH3OH > I° > II° > III°
→ → Reactivity of R’CO2H: HCOOH > RCH2COOH > R2CHCO2H > R3CCO2H
Chapter 9 – Alcohols – Chemical Reactions

• Increase yield by using one reactant in excess or removal of H 2O

• Remember that esterification: slow, athermic and reversible.

Fig. 9.7/pg 215

Catalytic Oxidation
(exothermic)

Fig. 9.8/pg 215

Catalytic Dehydrogenation

Mild Oxidation
Distinctive Properties
(endothermic)

(ALCOHOLS ARE
(1°& 2° alcohols ONLY) REDUCTANTS)

(I°):
• 1st, 3RCH2OH + Cr2O72- + 8H+ heat 3RCHO + 2Cr3+ + 7H2O
By Oxidants Cr3O72-,

RCOOH
• 2nd, 3RCHO + Cr2O72- + 8H+ replace 3RCHO + 2Cr3+ + 47H2O
MnO4-, etc.

2-
Excess Cr2O7 , acid major product; excess alcohol, aldehyde major product
(II°): 3R2CHOH + Cr2O72 + 8H+ 3R2CO + 2Cr3+ + 7H2O
(III°): no mild oxidation

Check figures 9.9, 9.10, 9.12, 9.12, 9.14, 9.15, 9.16, 9.17 / pg. 216-219