Question

Draw the curved arrow mechanism to show the conversion of hex-1-ene and CH3CH2OH in acidic solution into 2-ethoxyhexane. Follow the given instructions for each step. Draw all necessary atoms and charges; do not add any structures.

Answer 1

Answer:

             The formation of ether from alkene and alcohol in the presence of an acid take place in four steps.

Step 1:

          In first step the oxygen atom of alcohol abstracts the proton of acid and becomes a strong conjugate acid.

Step 2:

            Double bond of alkene being electron rich and nucleophilic in nature adds the proton from alcohol across its double bond and forms a stable carbocation (i.e. in this case a 2° carbocation).

Step 3:

           The oxygen atom of alcohol now attacks the electrophilic carbon (i.e. carbocation).

Step 4:

            The conjugate base of acid catalyst formed in first step abstracts the proton from oxonium ion and allows the final product to form as shown in attached reaction mechanism.