Chapter 18 Ketones and Aldehydes
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1 Chapter 18 Ketones and Aldehydes omenclature o Ketones have priority over alcohols Find the longest chain with the carbonyl in it. ame the parent and replace the e with one Say where the carbonyl is. octan-3-one When the ketone is not the high-priority group, you call the carbonyl oxo to name it. Common names: ame the two pieces coming off the carbonyl and call it ketone ethyl butyl ketone o Aldehydes have priority over ketones Find the longest chain with the carbonyl at the end. ame the parent and replace the e with al. 3-oxo-octanal Synthesis of ketones and aldehydes o xidation of alcohols Chromic Acid KMn4 CC Swern 1 R RC RC RC RC 2 R Ketone Ketone Ketone Ketone 3 R R R R R o zonolysis of alkenes
2 1) 3 2) DMS See Chapter 8 for review o Friedel-Crafts Acylation Cl AlCl3 See Chapter 17 for review o ydration of alkynes Acid-catalyzed 2S4 (aq) ydroboration-oxidation gs4 1) Sia2B 2) 22, - See Chapter 8 for review o Synthesis from carboxylic acids and acid chlorides Acids are first converted to acid chlorides. SCl2 Cl Acid chlorides are reduced to aldehydes with LiAl(tBu)3 1) LiAl(tBu)3 Cl 2) 2 LiCuR2 o LiCuR2 is like a specialty version of a Grignard that only replaces the Cl of acid chlorides.
3 Cl LiCu(C2C3)2 Wittig Reactions o verall reaction: turn a carbonyl into a carbon-carbon double bond. The carbon of the alkyl halide replaces the oxygen of the carbonyl. Br 3 BuLi C3 o Step one: Triphenylphosphine attacks an alkyl halide C3 Br o Step two: Grignard deprotonates to form the ylide What s an ylide? An ylide is when you have two atoms next to each other where one has a negative charge, the other has a positive charge, and they both have full octets. Bu Li o Step 3: ylide attacks the carbonyl o Step 4: - forms bond with
4 3 3 o Ring collapses fun with arrows 3 o Considerations: You want alkyl halide to be methyl or primary because they are best for S 2 ydration o Acid-catalyzed o Base-catalyzed o Rates This reaction doesn t happen to a large degree with most ketones It happens a little more with aldehydes Keq for formaldehyde is 40 Formation of Cyanohydrins o C is a toxic gas, so most often it is made in situ from excess ac and Cl. o Step one: cyanide ion attacks the carbonyl.
5 C - C o Step two: protonation C --C C o Things you can do with cyanohydrins. Catalytic hydration C 2/t ydrolysis C 3 4 C Formation of imines o verall: The nitrogen replaces the oxygen of the carbonyl, forming a carbonnitrogen double bond. It should be mildly acidic; p between 4 and 5. 3, o Mr. Baker said that you are not responsible for the mechanism, but here it is in case you want to look at it. o Step one: protonation of the carbonyl o Step two: Amine attacks the activated carbonyl
6 o Step three: Deprotonation o Step four: rotonation of hydroxyl o Step five: Loss of water : o Step six: Deprotonation Formation of acetals o You could call an acetal a geminal diether A hemiacetal is what you have when you re halfway there. It is one hydroxyl and one alkoxy group coming off the same carbon.
7 o Step one: protonation of the carbonyl o Step two: the alcohol attacks the activated carbonyl o Step three: deprotonation to give the hemiacetal o Step four: rotonation of the hydroxyl o Step five: water falls off o Step six: another alcohol adds
8 o Step seven: deprotonation gives the acetal Removing acetals o Use very dilute acid o The mechanism of hydrolysis of an acetal is just the same thing going backwards. Acetals and hemiacetals in sugars o Sugars exist in their cyclic forms as hemiacetals The carbon which is the hemiacetal or acetal is called the anomeric carbon. When the is up, it s Beta; when it s down, it s alpha. anomeric carbon o When they link up to become polysaccharides, they become acetals.
9 o Something you don t need to know for this class, but the MCAT expects you to know: Sugars that differ by only one chiral center are called epimers. C C C2 C 2 D-allose D-glucose rotecting groups o Requirements of a good protecting group Easy to put on onreactive under the reaction conditions Easily removable xidation of aldehydes o Aldehydes are oxidized to carboxylic acids by KMn4 and chromic acid Reductions of ketones and aldehydes o The following reductions which have already been seen work on ketones and aldehydes: ab4 LiAl4 2/ Raney i Zn(g)/Cl (aq) 24/base Ketone 2 R 2 R 2 R Alkane Alkane Aldehyde 1 R 1 R 1 R Alkane Alkane
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