Could 1-pentanol and 2-pentanol be converted to the bromide merely by shaking wi

Question

Could 1-pentanol and 2-pentanol be converted to the bromide merely by shaking with concentrated hydrobromic acid in the manner the 2-methyl-2-butanol did? How would you expect the results of the alkoxide-promoted eliminations to change if the alcohols used as solvents contained water? Would an amine be a good solvent for reaction one? Why or why not? What differences in product distribution would be expected for the elimination reactions of 2-bromo-2-methyibutane and 2-bromo-2, 3-dimethylbutane with excess potassium hydroxide in ethanol?

Explanation / Answer

1) Lucas test is converting alchol to alkyl halide

but it goes throgh carbocation intermediat

so here 1 pentanol will not react and there will be no reaction

2 pentanol is also ureactive but will react little if warmed

2) alkoxides are bulky nucleophiles hence they prefer to act as base and absract proton

from carbocation to give elimination but if there is little water is present itwill act as nucleophile and will give substitution product.

3) Amine will not be agood solvent becouse it will react with hydrobromic acid and make salt.

also it will react with carbocation formed and give diffrent product than expected.

4) 2 bromo 2 methyl butane will give secondary carbocation and it might give 50% of elimination and 50% substitution product but 2 bromo 2,3 Dimethyl butane will give you tertiary carbocation will give 100% elimination product

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