Answer to Question #165362 in Organic Chemistry for ADA

Question

Benzyl alcohol (C₆H₅CH₂OH) and benzoic acid may be obtained from benzaldehyde by the reaction with potassium hydroxide, using the method described below.

Benzaldehyde (26.5g) was added to a concentrated solution of potassium hydroxide in a corked bottle. The mixture was shaken and allowed to stand for several hours. Water was added and the mixture extracted with two separate portions of ether. The ether extracts were combined, dried, and distilled to give a liquid product A. The aqueous layer was acidified with concentrated hydrochloric acid and the white precipitate B filtered off by suction and purified. 10g of product A and 12g of product B were formed.

1. Calculate the percentage yield of B.
2. Sketch the apparatus you would have used for:

(i) Carrying out the ether extraction

(ii) Filtering off the product B.

Answer 1

Product A - 32.72%

Product B- 44.44%