Oximes are compounds containing a C=N-OH functional group. They are prepared by a condensation reaction of aldehydes or ketones with hydroxylamine under mildly acidic conditions. The reaction starts with a nucleophilic addition of hydroxylamine to the carbonyl group, which forms … Read more
Warfarin is an anticoagulant medication widely used to prevent and treat blood clots, including conditions such as deep vein thrombosis and pulmonary embolism. Chemically, it is a coumarin derivative, featuring a 4-hydroxycoumarin core linked to a substituted side chain. Its … Read more
Nucleophilic Additions to the Carbonyl Group In this chapter on aldehydes and ketones, we begin to see a new type of mechanism originating from the polar nature of the C=O carbonyl bond. When we say “different,” that is mainly compared … Read more
The Beckmann rearrangement is a reaction in which a ketone is first converted to an oxime, which, under acidic or Lewis acidic conditions, rearranges into an amide. This reaction is closely related to the Hofmann, Schmidt, and Curtius rearrangements, as … Read more
Preparation of Nitriles Nitriles can be prepared by substitution reactions of alkyl halides with cyanide salts: These are nucleophilic substitution reactions and we introduce the nitrile group by using the nucleophilicity of the cyanide ion. In a similar … Read more
There are a few ways of converting nitriles to amides. One of them is the sure way as it imposes no risk of your instructor counting it as invalid and taking some or all your points off. This is the … Read more
Alkynes to Ketones Alkynes can be converted to aldehydes and ketones via hydration reactions such as 1) Acid-Catalyzed Hydration, 2) Oxymercuration-Demercuration, and 3) Hydroboration-Oxidation. The first two are used for Markovnikov conversion of terminal alkynes to ketones, whereas the hydroboration-oxidation … Read more
When a beta hydroxy carbonyl compound is treated with a moderately strong base, such as a hydroxide or an alkoxide, an elimination occurs by expelling the hydroxyl group. The most common example is the aldol condensation reaction: So, … Read more
In this chapter on alpha carbon chemistry, you are going to come across the term “enol” almost in any new reaction. So, what is an enol? As the name suggests, these are species that contain an alkene (ene) and an … Read more
In the previous post, we talked about the Michael reaction, which is a conjugate-addition reaction of doubly stabilized enolates such as malonic ester, acetoacetic ester, and the like with ɑ, β-unsaturated carbonyl compounds: One important variation of the … Read more
