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The Wolff–Kishner reduction is a reaction used in organic chemistry to convert carbonyl functionalities into methylene groups. [1] [2] In the context of complex molecule synthesis, it is most frequently employed to remove a carbonyl group after it has served its synthetic purpose of activating an intermediate in a preceding step.
This page contains tables of azeotrope data for various binary and ternary mixtures of solvents. The data include the composition of a mixture by weight (in binary azeotropes, when only one fraction is given, it is the fraction of the second component), the boiling point (b.p.) of a component, the boiling point of a mixture, and the specific gravity of the mixture.
Density (g cm-3) Boiling point (°C) K b (°C⋅kg/mol) Freezing point (°C) K f (°C⋅kg/mol) Data source; Aniline: 184.3 3.69 –5.96 –5.87 K b & K f [1] Lauric acid: 298.9 44 –3.9 Acetic acid: 1.04 117.9 3.14 16.6 –3.90 K b [1] K f [2] Acetone: 0.78 56.2 1.67 –94.8 K b [3] Benzene: 0.87 80.1 2.65 5.5 –5.12 K b & K f [2 ...
In instructional laboratories, [5] acetophenone is converted to styrene in a two-step process that illustrates the reduction of carbonyls using sodium borohydride and the dehydration of alcohols: 4 C 6 H 5 C(O)CH 3 + NaBH 4 + 4 H 2 O → 4 C 6 H 5 CH(OH)CH 3 + NaOH + B(OH) 3 C 6 H 5 CH(OH)CH 3 → C 6 H 5 CH=CH 2 + H 2 O
Substance Formula 0 °C 10 °C 20 °C 30 °C 40 °C 50 °C 60 °C 70 °C 80 °C 90 °C 100 °C Barium acetate: Ba(C 2 H 3 O 2) 2: 58.8: 62: 72: 75: 78.5: 77: 75
2 C 6 H 5 CHO + KOH → C 6 H 5 CH 2 OH + C 6 H 5 COOK. The process is a redox reaction involving transfer of a hydride from one substrate molecule to the other: one aldehyde is oxidized to form the acid, the other is reduced to form the alcohol. [3]
The oxidation of primary alcohols to carboxylic acids normally proceeds via the corresponding aldehyde, which is transformed via an aldehyde hydrate (gem-diol, R-CH(OH) 2) by reaction with water. Thus, the oxidation of a primary alcohol at the aldehyde level without further oxidation to the carboxylic acid is possible by performing the reaction ...
The carboxylic acid in intermediate 4 is less basic than the alkoxide and therefore reversible proton transfer takes place favoring intermediate 5 which is protonated on acidic workup to the final α-hydroxy–carboxylic acid 6. Calculations show that an accurate description of the reaction sequence is possible with the participation of 4 water ...