The Problems in Converting Esters to Ketones Esters are carbonyl compounds susceptible to nucleophilic additions, and one may think of converting them to ketones using Grignard, organolithium, or organocuprate reagents. However, the problem with those is that Grignard and organolithium … Read more
Addition of Organolithiums to Carboxylic Acids One of the most common ways of converting carboxylic acids to ketones is their reaction with organolithiums. The first step is the deprotonation of the acid since organolithiums are also very strong … Read more
Aldehydes to Carboxylic Acids Aldehydes can be oxidized to carboxylic acids with a variety of oxidizing agents such as chromic acid, sodium dichromate, potassium permanganate, and sodium hypochlorite. Here is the summary of oxidizing agents we discussed in … Read more
In this conversion series, we mention how nitriles can be converted to ketones and aldehydes. Nitriles are converted to ketones by both Grignard and organolithium reagents: The new C-C bonds are formed by nucleophilic addition of the organometallic … Read more
Esters can be converted to alcohols by two types of reduction reactions. One is the reduction by a strong reducing agent such as LiAlH4 to a primary alcohol, and the second is the conversion to a tertiary alcohol by reacting … Read more
Amines from Alcohols Via Substitution Reactions Although amines are good nucleophiles, we cannot use them is a direct SN2 reaction to achieve the OH to NH2 conversion because the hydroxide ion is a poor leaving group. So, the … Read more
Alkenes to Aldehydes and Ketones via Ozonolysis Alkenes can be converted to aldehydes or ketones via ozonolysis, which is an oxidative cleavage reaction converting the C=C bond to a C=O bond. Whether an aldehyde or a ketone is obtained depends … Read more
To convert an alkene to an alkyne, we need to first halogenate it to prepare a dihalide, which can then be treated with a strong base such as sodium amide (NaNH2) to achieve a double elimination: A triple … Read more
