Consider the following pair of reactions. Predict the type
of elimination mechanism, predict which reaction of the pair will
occur at the fastest rate, and draw the correct organic
product.
My mechanisms are correct but I'm having an issue with the
structure.
Answer
General guidance
Decide the reaction mechanism based on the structure of the substrate (haloalkane) and the reagent (nucleophile/base) used.
Elimination reaction (E1 & E2): In order to decide the elimination reaction mechanism, following factors are considered:
• Polarity of solvent: The polarity of solvent increases the rate of E1 reaction mechanism.
• Strength of base: The stronger bases favor E2 reaction mechanism.
Step-by-step
Step 1 of 3
The reaction pathway for the given pair of reactions is E1.
The reaction proceeds through E1 reaction mechanism because a polar protic solvent 
is used both the reactions.
The base used is also a neutral weak base that also favors E1 reaction.
Step 2 of 3
The first reaction between the given pair is the faster one as shown beblow:
The first reaction is faster reaction because in an E1 reaction, the rate determining step is the first step involving the heterolytic cleavage of C-X (X=halogen) bond resulting in the formation of a carbocation as shown below:
The stability of carbocation determines the rate of reaction. In the first reaction, tertiary 
carbocation (carbon attached to three other carbons) is formed after the cleavage of C-Cl bond whereas in the second reaction, secondary 
carbocation (carbon attached to two other carbons) is formed.
The stability of carbocation is 
Hence, first reaction is faster and the second one is slower.
Step 3 of 3
The product formed in the pair of reactions are as follows:
The products of the pair of reactions are as follows:
The above products are obtained by the abstraction of the 
proton of the tertiary and secondary carbocations formed respectively in the previous step as shown below:
Answer
The products of the pair of reactions are as follows:
Answer only
The products of the pair of reactions are as follows: