Why are tertiary alkyl halides not used in Wurtz reactions?

The Wurtz reaction is restricted to the symmetric alkane’s synthesis. The Wurtz coupling method would generally fails when tertiary alkyl halides are used because tertiary alkyl halides include elimination reactions as side reactions. It is happened due to steric-hindrance.

Why only primary & secondary alkyl halide undergo Wurtz reaction but tertiary alkyl halide does not?

It should be noted that the ease of dehydrohalogenation of alkyl halide follows the order : tertiary > secondary > primary. Hence, primary and secondary alkyl halides undergo Wurtz reaction while tertiary alkyl halides undergo dehydrohalogenation to form alkenes.

How do primary secondary and tertiary alkyl halides differ?

organohalogen compounds classified as primary, secondary, or tertiary according to the degree of substitution at the carbon to which the halogen is attached. In a primary alkyl halide, the carbon that bears the halogen is directly bonded to one other carbon, in a secondary alkyl halide to two, and in a tertiary…

Why tertiary alkyl halide is more reactive than primary alkyl halide?

A tertiary carbocation is more stable than a secondary carbocation which is more stable than a primary carbocation. Greater the stability of the carbocation, greater will be the ease of formation of carbocation, and hence faster will be the rate of the reaction.

What happens when two different alkyl halides are taken in Wurtz reaction?

If two different alkyl halides are used in the Wurtz reaction to prepare an alkane with an odd number of carbon atoms, then a mixture of three alkanes is produced. It is because the two alkyl halides in addition to reacting with each other also react among themselves giving a mixture of three alkanes.

Why tertiary alkyl halide is not suitable for SN2 reaction?

(b) Tertiary alkyl halides do not react by an SN2 mechanism because the substrate blocks the approach of the nucleophile. The trigonal bipyramidal transition state cannot form because it is too sterically crowded.

What will happen if two alkyl halides are taken in Wurtz reaction?

Solution: If two different alkyl halides are used in the Wurtz reaction to prepare an alkane with an odd number of carbon atoms, then a mixture of three alkanes is produced. It is because the two alkyl halides in addition to reacting with each other also react among themselves giving a mixture of three alkanes.

Why tertiary alkyl halides do not undergo SN2 reaction?

Alkyl fluorides do not undergo nucleophilic substitution. Tertiary alkyl groups are less likely to react by the SN2 mechanism than pri- mary or secondary alkyl halides since the presence of three alkyl groups linked to the reaction center lowers the electrophilicity of the alkyl halide by inductive effects.

Why are tertiary alkyl halides more reactive?

Now, we know that tertiary carbocation is much more stable than secondary and the secondary carbocation is much more stable than the primary due to the inductive effect of the alkyl groups. Hence for SN1 reaction, the order of reactivity of the alkyl halides is tertiary > secondary > primary.

Why primary alkyl halide is more reactive than secondary?

It reacts faster in SN1 as alkyl groups are electron donating, therefore the halogen atom is more easily lost and the tertiary carbocation formed is more stable than a secondary carbocation due to the electron pushing effect of the three surrounding alkyl groups, meaning that there is more hyperconjugation and the …