Question

Which of the following reactions would NOT have a ""proton transfer step"" in the reaction mechanism: A 2-bromo-2-methylbutane + ​​ 2-methyl-2-butanol B 2-bromobutane + NaOH ​​ (E)-2-butene C 1-bromobutane + NaOMe ​​ methoxy butane D 2-bromo-2-methylbutane + tert-butoxide ​​ 2-methyl-1-butene

Answer 1

Reaction C

Explanation:

For reaction A) we have the production of alcohol by the action of the water that attacks the tertiary carbocation produced by the leaving of Br. In the last step we will have the proton transfer (figure 1).

For B) the proton transfer step is given in the double bond formation due to the attack of the hydroxle group (figure 2).

In C we have an Sn2 reaction. Therefore, the reaction takes place in only one step without the opportunity of a proton transfer step (figure 3).

Finally for D we have an elimination reaction in which the tert-butoxide molecule will remove hydrogen (proton transfer step) from the carbocation to produce an alkene (figure 4).