Draw the structures of major monohalo products in each of the following reactions:

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(N/A) $(i)$ Cyclohexanol reacts with $SOCl_2$ to form chlorocyclohexane: $\text{Cyclohexanol} + SOCl_2 \rightarrow \text{Chlorocyclohexane} + SO_2 + HCl$.
$(ii)$ $4-\text{Ethylnitrobenzene}$ undergoes free radical bromination at the benzylic position: $4-\text{Ethylnitrobenzene} + Br_2 \xrightarrow{\text{heat or UV light}} 4-(1-\text{Bromoethyl})\text{nitrobenzene} + HBr$.
$(iii)$ $4-\text{Hydroxymethylphenol}$ reacts with $HCl$ to replace the alcoholic $-OH$ group: $4-\text{Hydroxymethylphenol} + HCl \xrightarrow{\text{heat}} 4-\text{Chloromethylphenol} + H_2O$.
$(iv)$ $1-\text{Methylcyclohexene}$ undergoes electrophilic addition with $HI$ following Markovnikov's rule: $1-\text{Methylcyclohexene} + HI \rightarrow 1-\text{Iodo}-1-\text{methylcyclohexane}$.
$(v)$ $CH_3CH_2Br$ reacts with $NaI$ in acetone (Finkelstein reaction): $CH_3CH_2Br + NaI \rightarrow CH_3CH_2I + NaBr$.
$(vi)$ Cyclohexene undergoes allylic bromination with $Br_2$ under heat or $UV$ light: $\text{Cyclohexene} + Br_2 \xrightarrow{\text{heat or UV light}} 3-\text{Bromocyclohexene} + HBr$.

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Match the reactions in List-$I$ with the major products in List-$II$:
| List-$I$ | List-$II$ (Major Product) |
| :--- | :--- |
| $(A)$ $CH_3-CHBr-CH_2Br \xrightarrow{KOH/C_2H_5OH}$ | $(I)$ $1^{\circ}$-alkyl bromide |
| $(B)$ $CH_3-CH_2-CH=CH_2 \xrightarrow{HBr, (C_6H_5CO)_2O_2, \Delta}$ | $(II)$ $2^{\circ}$-alkyl bromide |
| $(C)$ $CH_3CH_2CH_3 \xrightarrow{Br_2, h\nu}$ | $(III)$ Allyl bromide |
| $(D)$ $CH_3-CH=CH_2 \xrightarrow{NBS, \Delta}$ | $(IV)$ Alkenyl bromide |

Which product would be expected to predominate in the given reaction?

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Which of the following cannot undergo nucleophilic substitution under ordinary conditions?

The total number of monohalogenated organic products (including stereoisomers) formed in the following reaction is:
$A$ (simplest optically active alkene) $\xrightarrow[(ii) X_2/\Delta ]{(i) H_2/Ni/\Delta }$

What will be the final major product?

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