What is the increasing order of reactivity of the following alkyl halides in the Williamson synthesis?
$I. \, CH_2 = CHCH_2Cl$
$II. \, CH_3CH_2CH_2Br$
$III. \, (CH_3)_3CCH_2Br$
$IV. \, CH_3CH_2CH_2Cl$

Match each of the compounds given in Column $I$ with the reaction$(s)$ that they can undergo,given in Column $II$.
| Column $I$ | Column $II$ |
| :--- | :--- |
| $(A)$ $3-$bromobenzofuran derivative | $(p)$ Nucleophilic substitution |
| $(B)$ Benzyl alcohol | $(q)$ Elimination |
| $(C)$ Salicylaldehyde | $(r)$ Nucleophilic addition |
| $(D)$ $1-$bromo$-2-$nitrobenzene | $(s)$ Esterification with acetic anhydride |
| | $(t)$ Dehydrogenation |

Which of the following compounds will evolve hydrogen on treatment with metal?

Match the reaction in Column-$I$ with the mechanism in Column-$II$.

Column-$I$ (Reaction)	Column-$II$ (Mechanism)
$A$. $CH_3OCH_2CH_3 + HI \to CH_3I + CH_3CH_2OH$	$i$. $S_{E}2$ Aromatic
$B$. $(CH_3)_3COCH_3 + HI \to CH_3OH + (CH_3)_3CI$	$ii$. $S_{N}1$
$C$. $C_6H_5OCH_3 + Br_2(CH_3COOH) \to p$-Bromoanisole	$iii$. Elimination $(\beta)$
$D$. $CH_3CH_2OH + H_2SO_4 (443 \ K) \to CH_2=CH_2$	$iv$. $S_{N}2$

Arrange the following $(w, x, y, z)$ in decreasing order of their boiling points.

Identify the reaction schemes $A, B, C$ for the conversion of vinylcyclohexane to the respective alcohols,given the following methods:
$I-$ Acid-catalyzed hydration
$II-$ Hydroboration-oxidation $(HBO)$
$III-$ Oxymercuration-demercuration