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Unformatted text preview: changes overall. (2 points) Look for the disappearance of a large (broad) peak at 3200-3650 cm-1 (O-H stretch), and the appearance of a large peak at ~1700 cm-1 (carbonyl stretch of the aldehyde). 3. Why cant tert-butanol be oxidized by sodium dichromate under the same conditions you will be using for your oxidation? Illustrate with a mechanism. (3 points) Tertiary alcohols dont have the beta proton necessary for the oxidation step: 4. Following the oxidation reaction, why do you wash the ether phase with 1M NaOH? (2 points) . This deprotonates the carboxylic acid to the water-soluble salt, and so it can be separated from the aldehyde which stays in the ether phase (purification)....
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- Spring '09