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320+Exam+2+Review+Sheet - Exam 2 Review Sheet Maleckar Chem...

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Exam 2 Review Sheet Maleckar Chem 320 Spring 2011 Chapter 17 Summary Naming Aldehydes & Ketones - be able to name aldehydes and ketones at the difficulty of the problems presented in class - remember that aldehyde names use the meth-eth-prop prefixes but end in “al” - remember that ketones are named in the same manner, but with an “one” ending - in both cases, the carbonyl carbon is given the lowest possible number - aldehydes and ketones take precedence over every other functional group we’ve covered so far, except for acids; aldehydes take precedence over ketones - you should know what acetyl, formyl, benzyl, and benzoyl groups are - you should know the few common names given in class (acetophenone, benzophenone, etc) - when an aldehyde and ketone are in the same compound, the ketone carbonyl is referred to as “oxo” and the compound is named as an aldehyde with a ketone group attached Structure of the Carbonyl Group - you should understand the bonding & bond angles - you should know that a carbonyl will give an absorbance of 1690-1750 cm -1 on an IR Preparation of Aldehydes and Ketones - be able to make aldehydes and ketones using ozonolysis, hydration of alkenes & alkynes, & Friedyl Crafts acylation - also be able to use oxidation: - Cr oxidation (Jones oxidation) is typically carried out in water; when you oxidize an alcohol to an aldehyde using Cr, and water is present, it is automatically oxidized to the acid – very difficult/impossible to stop at the aldehyde) - PCC oxidation involves Cr, but it doesn’t take place in water, so you can oxidize a primary alcohol to an aldehyde and it won’t proceed to the acid - MnO 2 selectively oxidizes primary and secondary allylic alcohols to the aldehyde/ketone. This will not oxidize any other types of alcohols. - you can also do hydroboration-oxidation on alkynes – you get anti-Mark. addition if you use a terminal alkyne, resulting in the aldehyde - if you do mercury-catalyzed hydration of a terminal alkyne, you get Mark. addition, ending in the methyl ketone - you can also react acid chlorides with organocuprates, giving an ester - you can also reduce esters and acid chlorides, giving aldehydes YOU DO NOT NEET TO KNOW THE MECHANISMS FOR THESE REACTIONS
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Reactivity of the Carbonyl Group…… - understand the two types of reactions carbonyl compounds can undergo: nucleophilic addition and deprotonation of the alpha H - we talked about these nucleophiles:
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