Fundamentals of Organic ChemistryChemistryHaloalkanes and Haloarenes
Consider the following two reactions: (i) (ii) Which of the two reactions proceeds at a faster rate, and what is the predominant mechanism for the formation of the alkene?
Options
- AReaction (i), E 1
- BReaction (i), E 2
- CReaction (ii), E 2
- DReaction (ii), E 1
Correct answer
A. Reaction (i), E 1
Step-by-step solution
The given reactions involve the elimination of HCl to form an alkene. The reagent used is 80 % H ₂ O / CH ₃ CH ₂ OH , which is a polar protic solvent mixture containing weak bases/nucleophiles. The absence of a strong base and the use of a highly polar ionizing solvent strongly favor the E 1 mechanism over E 2 . In the E 1 mechanism, the rate-determining step is the heterolytic cleavage of the C - Cl bond to form a carbocation intermediate. For reaction (i), the reactant is 2-chloro-2-methylpentane. Loss of the chl