Aldehydes and Ketones: Learning Goals

1. You can provide a proper, unique name for an aldehyde or ketone, given its structure.
2. You can draw a correct structure for an aldehyde or ketone, given its name.
3. You recognize the function of carbonyl oxygen as a Lewis base, and of the carbonyl carbon as a Lewis acidic, electron-deficient center. You recognize the polar nature of the carbonyl group.
4. You know the IR stretch for the C=O double bond, and you know how the carbonyl group affects proton and ¹³C chemical shifts in the NMR spectrum, and where carbonyl carbons in aldehydes and ketones appear in the ¹³C spectrum.
5. You remember how to make ketones and aldehydes via oxidation of alcohols. (Chapter 8)
6. You remember how to make ketones and aldehydes via ozonolysis of alkenes. (Chapter 11)
7. You recall that Friedel-Crafts acylation produces aromatic ketones. (Chapter 16)
8. You recall how to make ketones from alkynes. (Chapter 13)
9. You know that MnO₂ can selectively oxidize allylic alcohols to α, β-unsaturated ketones.
10. You know how to oxidize aldehydes to carboxylic acids, and know what a Tollens test (positive and negative) says about an organic compound.
11. You know the mechanism of nucleophilic addition to a carbonyl group.
12. You know how to apply this mechanism to hydration and cyanohydrin formation.
13. You know the mechanism for formation of acetals and ketals, and recognize the chemical realtionships with hemiacetals, hemiketals, thioacetals and thioketals.
14. You remember from Chapter 8 how to make alcohols by addition of hydride and Grignard type nucleophiles to aldehydes and ketones.
15. You know how amines, hydrazines, and related nitrogen compounds condense with ketones and aldehydes.
16. You know how to make a C=C double bond from a carbonyl using the Wittig reaction.
17. You know how to reduce ketones to methylene groups using the Wolff-Kischner and Clemmenson reductions.
18. You know how to make dithioacetals from ketones or aldehydes, and how the cyclic 1,3-dithianes formed from aldehydes can be used to make ketones. You know how to use Raney nickel to selectively reduce dithioacetals to a CH₂ group.
19. You recognize the reversible interconversion of ketones/aldehydes with acetals or dithioacetals provides a "protection/deprotection" strategy in multistep synthesis.
20. You understand how to use percarboxylic acids to do a Baeyer-Villiger oxidation of ketones to esters. You understand the basis of the relative migratory aptitude of different groups, and why methyl ketones always form acetates (and not methyl esters).