Why use nabh4 instead of lialh4

Insetad of an anionic donor that provides a hydride to a carbonyl, NADH is actually a neutral donor. It supplies a hydride to the carbonyl under very specific circumstances. Carboxylic acids can be converted to 1 o alcohols using Lithium aluminium hydride LiAlH 4.

Note that NaBH 4 is not strong enough to convert carboxylic acids or esters to alcohols. An aldehyde is produced as an intermediate during this reaction, but it cannot be isolated because it is more reactive than the original carboxylic acid. Give the aldehyde, ketone, or carboxylic acid there can be multiple answers that could be reduced to form the following alcohols.

Given the following alcohol, draw the structure from which it could be derived using only NaBH 4. Privacy Policy. Skip to main content. Search for:. The hydride anion is not present during this reaction; rather, these reagents serve as a source of hydride due to the presence of a polar metal-hydrogen bond.

Addition of a hydride anion H: — to an aldehyde or ketone gives an alkoxide anion, which on protonation yields the corresponding alcohol. In metal hydrides reductions the resulting alkoxide salts are insoluble and need to be hydrolyzed with care before the alcohol product can be isolated. For example consider the alkyls.

While CEt 4 3,3-diethylpentane is a very stable saturated hydrocarbon alkane the lead compound tetraethyl lead is unstable when it is heated. It breaks down with ease to form lead atoms and ethyl radicals. It used to be used in motor fuel petrol as an additive increase the octane rating but for public health reasons it has been withdrawn from use in petrol. The other ethyl compounds will have stabilities which will be partway between the alkane and the tetraalkyl lead.

I reason that as the central atom becomes more heavy the bonds between the whatever and the ethyl will become weaker. If you like my explanation of why one reducing agent is stronger than the other then please spread the good news by giving people the URL to this blog post. Now before I go I would like to point out that lots of fun chemistry other than the reduction of aldehydes and ketones can be done using sodium borohydride. For example the reaction of nickel chloride with sodium borohydride is a good way to make nanoparticles of nickel which are embedded in a boron oxide matrix.

This makes one of my favourite hydrogenation cataylsts. My academic interests include things from both nuclear chemistry, recycling and some other unrelated things. I originally come from the UK England. Thanks, Mark! Your Post makes chemistry easier. Never have seen such a nice and concise scheme explaining these reagents before. Any idea about how to reduce a conjugated carboxamide possibly requires LiAlH4 in the presence of a several keto groups conjugated in the same and in other electron systems?

Maybe you should consider using DIBAL-H Diisobutyl aluminium hydride as this reacts more quickly with the electron rich functional groups. Please name the exact compound you are being troubled by, and I may have a go at writing a blog entry on it. Please note that while I am willing to help students out, I hope that you are not trying to get me to do your homework or problem sheets for you.

Sir i am finding organic chemistry a bit difficult could you help me about how i should study ; my study schedule for organic chemistry is learning all the reaction and their mechanisms but still i do not know how to attempt a question any question given to me does not look like i have not been taught the theory for it but i am not able to attempt.

Sir , i am an iit aspirant so if you could help me as soon as possible the better it would be for me Thank You sir. This page is devoted to the […]. I used chemdraw for the diagrams, sometimes I copy the pictures into paint and then add extra bits.

I chanced upon your post whilst looking up reducing powers of these reagents. I looked at the mechanism for reduction of carbonyl compounds and noticed that for NaBH4, the sodium cation will coordinate with the oxygen of the carbonyl group when a H atom has been added.

However for LiAlH4, it is the aluminium that coordinates to said oxygen, not the lithium. Though, I can understand if both lithium and aluminium can coordinate to the oxygen.. So, does point 1 in your post still stand? Is it right to say that aluminium can coordinate more strongly to the oxygen, than lithium? Since aluminium is more positive and more electronegative than lithium.. Although this compound decomposes in neutral or acidic mediums, it is stable at pH The compounds that NaBH4 can reduce include organic carbonyls such as aldehydes and ketones, acyl chlorides, thiol esters, imines, etc.

LiAlH4 is lithium aluminium hydride which is a strong reducing agent. Its molar mass is It is a very strong reducing agent when compared to NaBH4 since this compound can reduce even esters, amides and carboxylic acids. NaBH4 is sodium borohydride, which is also a reducing agent. But, it is a mild reducing agent which cannot reduce esters, amides and carboxylic acids. Available here 2. Available here. With a mind rooted firmly to basic principals of chemistry and passion for ever evolving field of industrial chemistry, she is keenly interested to be a true companion for those who seek knowledge in the subject of chemistry.

Your email address will not be published. Figure Structure of Sodium Borohydride.