You combine concentrated HCl and 2-methyl-2-butanol in solution, allow the solut

Question

You combine concentrated HCl and 2-methyl-2-butanol in solution, allow the solution to boil, and collect the distillate. The resulting distillate is then analyzed via GCMS, IR, and NMR.

a) Your lab ran out of concentrated HCl, but has lots of 1 N HCl(aq). Is this a good substitute? Explain

b) Your lab ran out of 2-methyl-2-butanol, but has lots of 2-methyl-1-butanol. Is this a good substitute? Explain

c) Sn1 and E1 pathways often compete. Named the alkenes that might be formed in this reaction. Are they a significant side product? Explain

d) Carbocation rearrangements often compete in Sn1 reactions. Should you expect to find rearranged products in this experiment? Explain.

Explanation / Answer

a) 1N HCl will be the substitute but rate of reaction will be very slow

b) No...2-methyl-1-butanol is positional isomer of 2-methyl-2-butanol so will give you different product.

c) 2-chloro-2-methylbutane

d) It's true that carbocation rearrangements often compete in Sn1 reactions. But the given alcohol 2-methyl-2-butanol is not chiral. I have written bot the structures in the reaction since both are same due to symmetry. So here in this case you will isolate only one isomer.

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