What products will 2-methylbutan-2-ol give

[josephcollins]

What products will 2-methylbutan-2-ol give when reacted with excess concentrated H2SO4?

out of phenols with 2 methyl groups, an ether, a primary,secondary and tertiary alcohol, which will react most rapidly with sodium metal.


Could someone please help me with these,
thanks a lot,
Joe

 

[Sirus]

Please show us an effort at reasoning through these problems. You should be able to come up with some logical answers, as organic chemistry is not based on any memorized formulas, but on chemical thinking.

 

[josephcollins]

sorry sirus,
I would first imagine that the more R groups, the more polar the alcohol, so the more vigorous the reaction with Na+. there is also a very strong reaction with the phenol due to the electronegativity of the ring. But concerning the ether I do not quite know how the reaction will proceed, could someone help me with this step of the problem?

 

[chem_tr]

What products will 2-methylbutan-2-ol give when reacted with excess concentrated H2SO4?

out of phenols with 2 methyl groups, an ether, a primary,secondary and tertiary alcohol, which will react most rapidly with sodium metal.


Could someone please help me with these,
thanks a lot,
Joe

Dear Joe,

As 2-methylbutan-2-ol is a tertiary alcohol, its tendency to give an olefin is highest. If it is not a tertiary alcohol, principally seek for other mechanisms, such as ether formation (which is favorable in sulfuric acid media). So a total of at least two mechanisms (and therefore two main products) will be present, I think, with different percentages, of course.

About your second question, please remember that stability increases with increasing R groups, which is indicative of decreasing reaction ability. Phenols are more acidic than ordinary alcohols, as the phenyl group pulls oxygen's electrons, so releasing hydrogen more than that in aliphatic alcohols. However, methyl groups in ortho- and para-positions decrease this acidity to some extent. Ethers are the most stable compounds in this series.

According to the information I gave above, give some feedback.