Chapter 10.5, Problem 10.11P

Interpretation Introduction

Interpretation:

The major product and minor product that is expected has to be drawn when the given compound is heated with concentrated sulfuric acid to give an E1 reaction.

Concept Introduction:

Elimination reactions are the one in which the groups are lost and the saturated bonds are converted to unsaturated bonds.  Usually the substitution reaction competes with elimination reaction.

In elimination reaction, the beta proton is removed together with the leaving group to form a double bond.

E1 reaction proceeds through two separate single steps.  First step is the formation of carbocation intermediate by loss of leaving group.  Second step is the attack of base to lose a proton.  E1 stands for unimolecular elimination.

First step is the rate determining step.  Hydroxide group is a poor leaving group.  Hence, for elimination reaction, a very strong acid is required to protonate the hydroxyl group.  When an alcohol is heated with concentrated sulfuric acid, the product obtained is an alkene with a loss of water molecule.  The proton is abstracted by the base, in order to form the more substituted alkene (Zaitsev product) as the major one.  The other alkene will be a minor one.