So far, we’ve seen a variety of nucleophiles in organic chemistry – halides, hydroxides, alkoxides, thiols, etc. Most of these nucleophiles contain heteroatoms like oxygen, nitrogen, or sulfur, but nucleophiles can also be carbon-based, and these are among the most … Read more
We’ve been covering the key reactions and mechanisms of aldehydes and ketones, how they react with water to form hydrates, with alcohols to give hemiacetals and acetals, with amines to form imines and enamines, and with Grignard and other nucleophiles … Read more
There are a few ways to convert nitriles to esters. Let’s start with the Pinner reaction, which, although not commonly highlighted in textbooks, is a direct and efficient method for this transformation. Pinner Reaction for Converting Nitriles to Esters … Read more
Ketones can be converted to esters through the Baeyer–Villiger oxidation, where a ketone reacts with a peracid (like mCPBA) to insert an oxygen atom next to the carbonyl, forming an ester. Notice that the more substituted alkyl group of … Read more
Acetals are organic compounds in which a carbon atom is bonded to two alkoxy groups (-OR). They don’t look much like a carbonyl compound, so why do we need to talk about them in the chapter on aldehydes … 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
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This content is for registered users only. Click here to Register! By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction … 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
Baeyer-Villiger Oxidation The Baeyer-Villiger oxidation is a rearrangement reaction that converts ketones to esters using peroxycarboxylic acids, such as meta-chloroperoxybenzoic acid (mCPBA). The Baeyer–Villiger oxidation can also convert aldehydes into carboxylic acids, but let’s be honest, including that as a key use … Read more
