What is the major product formed in the following reaction?

In $S_N1$ reaction, the alkyl halide that on hydrolysis produces a racemic mixture is

The major product '$Y$' in the following reaction is

Which of the following compounds is most reactive towards $S_N1$ reaction?

What is $E$?
Cyclohexanone $\xrightarrow{Br_2 + CH_3COOH} A$ $\xrightarrow{Alc. KOH} B$ (Product with six-membered ring) $\xrightarrow[(2) H_2O]{(1) CH_3MgBr} C$ $\xrightarrow{H^{\oplus} + \Delta} D$ $\xrightarrow{HBr (1 \text{ mole})} E$

Given below are two statements $:$
Statement $(I) :$ $cis-1,2-dichloroethene$ is more polar than $cis-1,2-dibromoethene$.
Statement $(II) :$ Boiling point of $trans-1,2-dibromoethene$ is lower than $cis-1,2-dibromoethene$ but it is more polar than $cis-1,2-dibromoethene$.
In the light of the above statements,choose the most appropriate answer from the options given below $:$