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Benzyl Alcohol and Benzoic Acid from Benzaldehyde and Strong Potash (Cannizzaro, Gattermann 1914)
Strong potash splits benzaldehyde in two: half is reduced to benzyl alcohol, half oxidised to benzoic acid (as potassium benzoate). 20 g of benzaldehyde gives about 8 g of benzyl alcohol, boiling at 206 °C; the benzoic acid is thrown down with hydrochloric acid.
Not given: the volumes of water and ether, the amount of hydrochloric acid and the benzoic acid yield.
Source: L. Gattermann, Practical Methods of Organic Chemistry (1914 ed.), Reaction 25, pp. 303-304. Picture: our drawing.
Katamtaman
1 night plus a few hours
Mga Tagubilin
1
1
Shake with strong potash
Shake with strong potash
Dissolve 18 g of potassium hydroxide in 12 g of water and let it cool. Put 20 g of benzaldehyde in a stoppered cylinder or other thick-walled vessel, add the cold potash and shake until a lasting emulsion forms.
Mga materyales para sa hakbang na ito:
Benzaldehyde1 20 g
Potassium hydroxide1 18 g
Tubig1 12 gMga kailangang kasangkapan:
Timbangan
Silindrong panukat
Mga tapon na kortsa2
2
Stand overnight
Stand overnight
Close the vessel with a cork, not a glass stopper (a glass stopper can stick fast), and let it stand overnight. A crystalline paste of potassium benzoate separates.
Mga kailangang kasangkapan:
Silindrong panukat
Mga tapon na kortsa3
3
Extract with ether
Extract with ether
Add water until the paste dissolves to a clear solution. Shake it out several times with ether to take up the benzyl alcohol, keeping the watery alkaline layer for the benzoic acid.
Mga materyales para sa hakbang na ito:
Tubig1 amount not given
Diethyl ether1 amount not givenMga kailangang kasangkapan:
Embudong panghiwalay
Basong Salamin na Pang-agham4
4
Distil the benzyl alcohol
Distil the benzyl alcohol
Evaporate the ether and distil the residue. Benzyl alcohol passes over at 206 °C. Yield: about 8 g.
Mga kailangang kasangkapan:
Water Bath
Prasko ng Salamin sa Distilasyon
Kondenser na pinalalamig ng tubig
Termometro
Bunsen burner5
5
Precipitate the benzoic acid
Precipitate the benzoic acid
Acidify the alkaline solution with hydrochloric acid; benzoic acid is thrown down. Filter it off.
Mga materyales para sa hakbang na ito:
Hydrochloric acid1 amount not givenMga kailangang kasangkapan:
Basong Salamin na Pang-agham
Embudong Salamin na May Tangkay
Papel na PansalaMga Materyales
5- 1 20 gPlaceholder
- 1 18 gPlaceholder
- 1 amount not givenPlaceholder
- 1 amount not givenPlaceholder
- 1 amount not givenPlaceholder
Mga Kinakailangang Kasangkapan
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