A student spotted a mixture of benzaldehyde and benzyl alcohol on a TLC plate. S

Question

A student spotted a mixture of benzaldehyde and benzyl alcohol on a TLC plate. She then dev TLC plate in ethy acetate and obtained the following result: 5 pts eloped the aldehye alcohe TLC Plate after ethyl acetate benzaldehyde benzyl alcohol Label the spots on the plate above to indicate Fill in beiow what the developed plate would have looked like if the stüdent had run the plate in hexane instead of ethyl acetate and label your spotis) to indicate which compound each represents a. which is benzaldehyde and which is benzyi alcohol. nonpolar alehyde. olcoho mote as

Explanation / Answer

When two different compounds run under identical chromatography condition the compound with larger Rf value is less polar because it interacts less strongly with the polar adsorbents on the TLC plate. So compound with low polarity will move more. In Alumina plate   the functional polarity order of Benzaldehyde and benzyl alcohol is

Benzaldehyde< Benzyl alcohol. This is because of H-bonding between alcohol and Alumina. So Benzyl alcohol has a strong interaction with Alumina which prevents the compound to move.

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