What is the reactivity difference between LiAlH4 and NaBH4?

What is the reactivity difference between LiAlH4 and NaBH4?

NaBH4 is less reactive than LiAlH4 but is otherwise similar. It is only powerful enough to reduce aldehydes, ketones and acid chlorides to alcohols: esters, amides, acids and nitriles are largely untouched.

Why is LiAlH4 stronger than NaBH4?

Lithium aluminium hydride (LiAlH4) is more electropositive (more metallic) than boron in NaBH4. The hydride from LiAlH4 is therefore more electron rich and thus is a stronger base (in reaction with water) and stronger nucleophile (with carbonyl group).

Is LiAlH4 or NaBH4 stronger?

When comparing NaBH4 with LiAlH4, the metal-hydrogen bond of LiAlH4 is more polar; thus, it is a stronger reducing agent than NaBH4. This is mainly because aluminum in LiAlH4 is more electronegative than boron in NaBH4. Below infographic gives a detailed comparison related to the difference between NaBH4 and LiAlH4.

Why is lithium Aluminium hydride is a better reducing agent than sodium borohydride?

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. Because aluminium is less electronegative than boron, the Al-H bond in LiAlH4 is more polar, thereby, making LiAlH4 a stronger reducing agent.

What does NaBH4 do in a reaction?

Sodium borohydride (NaBH4) is a reagent that transforms aldehydes and ketones to the corresponding alcohol, primary or secondary, respectively.

Does NaBH4 reduce double bond?

LiAlH4 reduces double bond only when the double bond is Beta-arly , NaBH4 does not reduce double bond. if you want to you can use H2/Ni to reduce a double bond.

Why is LiAlH4 violent with water?

The hydride ion in LiAlH4 is very basic. For this reason, LiAlH4 reacts violently with water and therefore must be used in dry solvents such as anhydrous ether and THF. Like many other strong bases, the hydride ion in LiAlH4 is a good nucleophile, and LiAlH4 contains its own “built-in” Lewis acid, the lithium ion.

Can NaBH4 reduce nitro groups?

[Google Scholar] It is known that solely sodium borohydride does not reduce nitro compounds under ordinary conditions. However, the reducing power of this reagent or its polymeric analogue (BER) undergoes a drastic change toward reduction of nitro groups by the combination with metal halides or salts2.

Is NaBH4 a catalyst?

The recent development of the NaBH4-PEMFC system lies in the development of a sodium borohydride hydrolysis catalyst, the design of a hydrogen production device, and the optimization of the system performance. This has resulted in sodium borohydride becoming the first choice of new hydrogen generation sources.

How does NaBH4 reduce?

Sodium borohydride is a relatively selective reducing agent. Ethanolic solutions of sodium borohydride reduce aldehydes and ketones in the presence of epoxides, esters, lactones, acids, nitriles, or nitro groups.

Can NaBH4 reduce Cinnamaldehyde?

Sodium borohydride reduces cinnamaldehyde via 1,2-reduction in hydroxylic solvent to cinnamyl alcohol in 97\% yield.

Can LiAlH4 reduce triple bond?

* LiAlH4 reagent can reduce aldehydes to primary alcohols, ketones to secondary alcohols, carboxylic acids and esters to primary alcohols, amides and nitriles to amines, epoxides to alcohols and lactones to diols. However, the double or triple bonds in conjugation with the polar multiple bonds can be reduced.

What is the difference between NaBH4 and LiAlH4 reaction?

The key difference between NaBH4 and LiAlH4 reaction is that NaBH4 is a weak reducing agent, while LiAlH4 is a strong reducing agent. Both NaBH4 and LiAlH4 are reducing agents.

What is the difference between LiAlH4 and DIBAL-H?

One major difference between these reagents are that LiAlH4 and NaBH4 are nucleophillic hydride donors while DiBAL-H are electrophillic hydride donors. The difference also lies between the reducing capacity of these reducing agents.

Can NaBH4 handle esters and carboxylic acids?

NaBH4 can handle esters, but it is very slow at converting them and thus not preferable. We then learn that if you want to turn esters and carboxylic acids into alcohols, we better use LiAlH4 because it is a strong reducing agent. LiAlH4 can convert aldehydes, ketones, esters,…

Is LiAlH4 a reducing agent or reducing agent?

Both LiAlH4 and NaBH4 are reducing agents. But LiAlH4 is a very strong reducing agent than NaBH4 because the Al-H bond in the LiAlH4 is weaker than the B-H bond in NaBH4.