Why LiAlH4 Cannot reduce tertiary alkyl halide?

Answers. AlLiH4 is normally used to reduce 1 degree halide, the reason being that during the process of the reaction, Al develops a negative charge. Being a metal it cannot handle the charge and instantly gives out a hydride ion.

What are the groups that NaBH4 can and Cannot reduce?

Sodium borohydride 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 does only tertiary alkyl halide undergo elimination in Wurtz reaction?

Nucleophilic attack on a tertiary alkyl halide is extremely slow because of steric hindrance. That’s why the Wurtz reaction does not work with tertiary alkyl halides.

Why NaBH4 Cannot reduce Ester?

At this point, the reactivity is too weak to occur without a stronger reducing agent. The short answer is that NaBH4 is simply too weak a reducing agent for carboxylic acids and esters and the two will simply mingle in solution with little to no reaction for months.

Does NaBH4 reduce alkyl halide?

Sodium borohydride, a representative borohydride reagent, behaves as an effective source of nucleophilic hydride in an aprotic polar solvent, such as DMSO, sulfolane, HMPA, DMF or diglyme, and is used for the reduction of alkyl halides.

What reaction fails in case of tertiary alkyl halide?

Wurtz reaction fails in case of tertiary alkyl halides.

Which alkyl halides do not undergo Wurtz reaction?

Wurtz reaction fails in case of tert-alkyl halides.

Why is NaBH4 a weak reducing agent?

The key difference between LiAlH4 and NaBH4 is that LiAlH4 can reduce esters, amides and carboxylic acids whereas NaBH4 cannot reduce them. 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. This makes the Al-H bond less stable.

How does alkyl halide reduce?

The alkali metals (Li, Na, K etc.) In a similar fashion these same metals reduce the carbon-halogen bonds of alkyl halides. The halogen is converted to halide anion, and the carbon bonds to the metal (the carbon has carbanionic character).