Diisobutylaluminium hydride, also known as (DIBAL, DIBALH, DIBAL-H or DIBAH) is a bulky reducing agent that is mainly used for converting esters and nitriles to aldehydes. The reaction is carried out at lower temperatures (typically -78 oC as that is the … Read more
Amides are the least reactive derivatives of carboxylic acids, so reducing them requires using the strong reducing agent LiAlH4. The reduction converts primary, secondary, tertiary cyclic, and acrylic amides to corresponding amines: The Mechanism of Amide Reduction by … Read more
Carboxylic acids can be reduced to primary alcohols using an excess of strong reducing agents such as lithium aluminum hydride (LiAlH4 or LAH). As sodium borohydride (NaBH4) is the most common reducing agent we learn about together with … Read more
Aldehydes and ketones are carbonyl compounds, and the carbon here is in a relatively high oxidation state: Notice that the oxidation state of the carbon decreases with the number of hydrogens connected to it. On the contrary, the … 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
When alkynes are reacted with water, aldehydes and ketones are formed. While internal alkynes can only be converted to ketones by acid-catalyzed hydration or oxymercuration-demercuration, terminal alkynes can also be converted to aldehydes via anti-Markovnikov addition of hydroboration-oxidation: … Read more
Reductive amination is used for preparing amines from aldehydes and ketones. All we need is to mix an amine with an aldehyde or ketone in the presence of sodium cyanoborohydride (NaBH3CN) at lower pH levels: So, how does … Read more
We learned in general chemistry that the oxidation state is determined based on the number of bonds connecting elements with different electronegativities. Very often, though, we didn’t need/bother to look at the number of bonds, but simply used a formula … Read more
The carbonyl group in aldoses and ketoses can be reduced by NaBH4 to a 1o and 2o alcohol, respectively. The product of this reaction is a polyalcohol called an alditol. The reduction of the ketones creates a new … Read more
A variety of reactions that we have seen earlier can be used for preparing amines. The most straightforward would look like an SN2 reaction of an alkyl halide with ammonia or an amine: The main drawback of this … Read more
