[perivar]

In a laboratory experiment i am to synthesise three alkyhalides, 1 - bromopropane, 2 - bromobutane and 2 - bromo - 3 - methylpropane from their respective alcohols with HBr. After refluxing and distillation, one is to wash 1 - bromopropane and 2 - bromobutane with 1/5 of their volume with HCl in a separation funnel, but not with 2 - bromo - 3 - methylpropane. I tried to figure out that by washing with HCl, one would extract out the water from the alkylhalids, but with if HCl is washed with 2 - bromo - 3 - methylpropane, one would get by - products from substitution, but i am not sure on this.

[perivar]

In a laboratory experiment i am to synthesise three alkyhalides, 1 - bromopropane, 2 - bromobutane and 2 - bromo - 3 - methylpropane from their respective alcohols with HBr. After refluxing and distillation, one is to wash 1 - bromopropane and 2 - bromobutane with 1/5 of their volume with HCl in a separation funnel, but not with 2 - bromo - 3 - methylpropane. If HCl is washed with 2 - bromo - 3 - methylpropane, one would get by - products from substitution, but i am not sure on this.

[discodermolide]

So what is your question?

[perivar]

So what is your question?

Why not washing 2 - bromo - 2 - methylpropane with HCl?

[discodermolide]

I would think it would hydrolyse to t-butanol and/or give isobutylene.