Direct Conversion of Acid Chlorides to Ketones Acid chlorides also known as acyl chlorides (ROCl) can be converted to ketones in direct and indirect transformations. The direct conversation is achieved by their reaction with organocuprates (Gilman reagent – R2CuLi). … 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
Primary amides can be converted to aldehydes and ketones via nitriles. So, the first thing we need here is a strong dehydrating agent such as SOCl2, P2O5, and POCl3 to convert the amide to a nitrile: Amides to Aldehydes … Read more
In the previous post, we saw that amides can be reduced to amines by LiAlH4: Let’s see how tertiary amides can be reduced to amines and aldehydes using alkyboranes. Reduction of Amides by Alkylboranes The reduction of amides … Read more
In this post, we will discuss the reduction of carboxylic acids and their derivatives, such as acid chlorides, esters, amides, and nitriles. Let’s start with carboxylic acids. Reduction of Carboxylic Acids Carboxylic acids can be converted to alcohols using … Read more
There are a few ways of converting carboxylic acids to esters, and the first one is the direct reaction between the acid and an alcohol. This is known as the Fischer esterification which is a type of addition-elimination reaction of … Read more
Let’s discuss how esters can be converted to aldehydes. In the previous post, we saw that esters can be reduced to primary alcohols using a strong reducing agent such as LiAlH4: Now, we can of course oxidize the … Read more
We know that aldehydes and ketones react with one equivalent of Grignard reagents, producing secondary and tertiary alcohols, respectively. Esters, on the other hand, react with two equivalents of Grignard reagents, producing tertiary alcohols: What happens is we have … Read more
Carboxylic acids can be converted to alcohols using an excess of strong reducing agents such as LiAlH4. The excess reducing agent is needed because first we are going to have a deprotonation of the carboxylic acid, and … Read more
