Aldehydes and Ketones.
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What 2 steps are needed to turn a carboxylic acid into an aldehyde?
The carboxylic acid needs to be reduced to a primary alcohol. The primary alcohol needs to be oxidised to an aldehyde.
What are 2 good reagents for the 2 steps of turning a carboxylic acid into an aldehyde?
Step 1: LiAlH4, dee, water. Step 2: PCC, CH2Cl2.
What are the 2 steps of turning an aldehyde into a ketone?
Aldehyde to secondary alcohol. Secondary alcohol to ketone.
What are the important factors of the cyanohydrin formation?
A new carbon-carbon bond is formed. CN group can be converted to COOH and CH2NH2. OH group can undergo functional group transformations.
What is a hemiacetal formation?
OH I R-C-H I O-R
What is an acetal formation?
O-R I R-C-H I O-R
What is a hemiketal formation?
OH I R-C-CH3 I O-R
What is a ketal formation?
O-R I R-C-CH3 I O-R
What is the Wittig reaction used for?
Conversion of aldehydes and ketones to alkenes.
What is the Baeyer Williger reaction used for?
The oxidation of ketones.
Ketones and aldehydes are what kind of group?
Carbonyl.
The carbonyl carbon has what hybridisation?
SP2.
In an aldehyde or a ketone what hybridisation is the oxygen?
SP2.
What are good reagents to turn a secondary alcohol into a ketone?
Chromic acid or KMnO4.
How can more complicated ketones be made?
Complicated ketones can be made by the oxidation of alcohols, which in turn can be made from reaction of a Grignard and an aldehyde.
How are aldehydes made?
Aldehydes are made from the oxidation of primary alcohols. This oxidation needs to be done carefully to avoid over-oxidation to carboxylic acids.
What is ozonolysis?
Alkenes can be cleaved by ozone (followed by a mild reduction) to generate aldehydes and/or ketones.
What is an excellent method for the preparation of alkyl aryl ketones?
Friedal Crafts acylation.
What is dithiane?
Dithiane has relatively acidic hydrogens located between the two sulfur atoms.
How can the acidic hydrogens be removed from diathiane?
These can be removed by a strong base.
How can dithiane anion can react with primary alkyl halides?
The dithiane anion can react as a nucleophile with primary alkyl halides, and this alkylation generates a thioacetal.
The hydrolysis of a thioacetal generates what?
The hydrolysis of a thioacetal generates an aldehyde.
How can the thioacetal can be turned to a ketone?
The thioacetal can be further deprotonated and reacted with another (different) alkyl halide to generate a new thioacetal with two alkyl substituents. On hydrolysis, this thioacetal produces a ketone.
What is is a good route for the construction of unsymmetrical ketones?
The further hydrolysis of a thioacetal.