Rules of the Day 12 - atom Like acetal formation this...

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Rules of the Day 2-16-09 1. When the aldehyde and an alcohol group are 4 or 5 carbons away on the same molecule, a relatively stable five- or six-membered ring cyclic hemiacetal is formed . 2. Carbohydrates exist in the cyclic, hemiacetal form in solution . Click here for a "molecule of the day" that discusses much of this. The mechanism involves the same steps as the cyclic hemiacetal formation mechanism. 3. Imines are formed when a primary amine or ammonia reacts with an aldehyde or ketone with some acid around. The mechanism involves mechanism C to make a aminal, followed by protonation of the OH group then loss of water at the same time a proton is lost from the nitrogen
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Unformatted text preview: atom. Like acetal formation, this process is reversible and can be run in either direction depending on the ratio of amine (ammonia) to water in the solution. 4. Imines can be reduced as they are made to give amines if H2/Pd is added to the reaction. 5. Aldehydes are easily oxidized to carboxylic acids using H2CrO4 in H2O. 6. Aldehydes and ketones can be reduced by H 2 /Pd to give alcohols. (Watch for racemic mixtures!) Note that this method will also reduce any carbon-carbon double or triple bonds that happen to be in the molecule....
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