Rearrangements can occur during the dehydration of 1° alcohols even though no 1° carbocati...

Rearrangements can occur during the dehydration of 1° alcohols even though no 1° carbocation is formed-that is, a 1,2-shift occurs as the C - OH2+ bond is broken, forming a more stable 2° or 3° carbocation, as shown. Using this information, draw a stepwise mechanism that shows how CH3CH2CH2CH2OH is dehydrated with H2SO4 to form a mixture of CH3CH2CH = CH2 and the cis and trans isomers of CH3CH2=CHCH3. We will see another example of this type of rearrangement in Section 18.5C.