Heterolytic bond dissociation energy of alkyl halides follows the sequence:

Find the reactants which on heating with alcoholic $KOH$ produce the compound $CH_3-CH_2-CH_2-CH=CH_2$.
$(i) \ CH_3-CH(Br)-CH_2-CH_2-CH_3$
$(ii) \ CH_3-CH_2-CH(Br)-CH_2-CH_3$
$(iii) \ CH_3-CH_2-CH_2-CH_2-CH_2Br$
$(iv) \ CH_3-CH_2-CH_2-CH(Br)-CH_3$

Match the reactions in List-$I$ with the features of their products in List-$II$ and choose the correct option.
| List-$I$ | List-$II$ |
| :--- | :--- |
| $(P)$ $(-)-1$-Bromo-$2$-ethylpentane $\xrightarrow{aq. NaOH, S_N2}$ | $(1)$ Inversion of configuration |
| $(Q)$ $(-)-2$-Bromopentane $\xrightarrow{aq. NaOH, S_N2}$ | $(2)$ Retention of configuration |
| $(R)$ $(-)-3$-Bromo-$3$-methylhexane $\xrightarrow{aq. NaOH, S_N1}$ | $(3)$ Mixture of enantiomers |
| $(S)$ $(3S, 5S)-5$-bromo-$3$-methylheptane $\xrightarrow{aq. NaOH, S_N1}$ | $(4)$ Mixture of structural isomers |
| | $(5)$ Mixture of diastereomers |

Arrange the following halides in the decreasing order of their reactivity towards $S_{N^1}$ reaction.
$(I) \ CH_3CH_2CH_2Cl$ $(II) \ CH_2 = CH - CH(Cl)CH_3$
$(III) \ CH_3CH_2CH(Cl)CH_3$

Which of the following rules applies in the reaction:
$CH_3CHBrCH_2CH_3 \xrightarrow{alc. KOH}$
$(i)$ $CH_3CH = CHCH_3$ (major product)
$(ii)$ $CH_2 = CHCH_2CH_3$ (minor product)

Reaction of $(R)-2$-butanol with $p$-toluenesulphonyl chloride in pyridine followed by $LiBr$ gives: