Which of the following processes does $NOT$ occur during the preparation of $CHCl_3$ from $C_2H_5OH$ and bleaching powder?

Given below are two statements:
Statement $I$ : $C_2H_5OH$ and $AgCN$ both can generate nucleophile.
Statement $II$ : $KCN$ and $AgCN$ both will generate nitrile nucleophile with all reaction conditions.
Choose the most appropriate option :

Identify the product obtained when $2-\text{chloro}-2-\text{methylbutane}$ is reacted with sodium metal in the presence of dry ether.

The ascending order of relative rate of solvolysis of the following compounds is:

$CH_3-CH_2-CH(Br)-CH_3 \xrightarrow{Alc. KOH} X$ (major)
$CH_3-CH_2-CH(NMe_3^+) - CH_3 \xrightarrow{EtONa, \Delta} Y$ (major)
Product $(X)$ and $(Y)$ respectively are:

When $3-$methylbutan$-2-$ol is treated with $HBr$,the following reaction takes place:
$CH_3-CH(CH_3)-CH(OH)-CH_3 \xrightarrow{HBr} CH_3-C(Br)(CH_3)-CH_2-CH_3$
Give a mechanism for this reaction.
(Hint : The secondary carbocation formed in step $II$ rearranges to a more stable tertiary carbocation by a hydride ion shift from $3^{rd}$ carbon atom.)