Aldehydes and Ketones Flashcards
Nitrile Reduction
1) DIBAL-H 2) H2O
DIBAL (DIBAL-H or DIBAH) is a strong, bulky reducing agent.
- Makes aldehydes
Acyl Halide Reduction
1) LiAlH(O-t-Bu)3 2) H2O or
1) DIBAL-H 2) H2O
- Makes aldehydes
Ester Reduction
1) DIBAL-H 2) H2O
- Makes aldehydes
Primary Alcohol Oxidation
PCC
- Makes aldehydes
Secondary Alcohol Oxidation
H2CrO4, H2O
- Starting as an alkene
- Makes ketones
- If these reagents were used on a primary alcohol, it would result in a carboxylic acid
Ozonolysis
1) O3 2) Me2S with appropriate alkenes
- Makes ketones and aldehydes because the use of Me2S (perseveres the hydrogens)
Swern Oxidation
1) DMSO, (COCl)2 2) Et2N @low temp.
Primary alcohol: Aldehyde
Secondary alcohol: Ketone
Friedel-Crafts Acylation
1) ArH, AlCl3 2) H2O
- Making an aromatic ketone, starting with an acyl halide
Grignard with Nitrile
1) R”MgBr or R”Li 2) H3O+
The same process in the creation of the desired Grignard reagent
Acetal and Hemiacetal Hydrolysis
H2O, H+ (SA?)
Acid-Catalyzed Hydrolysis
- Similar process
Hemiacetal and Acetal Formation
The opposite process of the Acid-Catalyzed: rather you are adding the
Wolff-Kishner Reduction
H2NNH2, HO-, Heat
- Reduce to an alkane
Alkynide Anion Addition
1) RC—C- 2) H3O+
(It is not the exact mechanism, but it follows the same process)
- RC—C- acts as an electrophile and attacks the carbon attached to the O=
- Similar to alkylation of a terminal alkyne reaction
Nitrile Addition (cyanohydrin formation)
1) NC- 2) H3O+
Wittig Synthesis of Alkenes
1) CHR3R4Br, (C6H5)3P
2) RLi (as strong base)
Enamine Synthesis
1) R2NH cat. HA
Baeyer-Villiger Oxidation
RCO3H
Making esters
Imine Synthesis
1) RNH2, cat. HA
