Which of the following groups deactivates the benzene ring towards electrophilic substitution reaction?

Given below are two statements: one is labelled as Assertion $(A)$ and the other is labelled as Reason $(R)$.
Assertion $(A)$ : Chlorine is an electron withdrawing group but it is ortho,para directing in electrophilic aromatic substitution.
Reason $(R)$ : Inductive effect of chlorine destabilises the intermediate carbocation formed during the electrophilic substitution,however due to the more pronounced resonance effect,the halogen stabilises the carbocation at ortho and para positions.
In the light of the above statements,choose the most appropriate answer from the options given below :

What is the correct order of $o/p$ ratio when $E^{+}$ attacks the following systems?
$(A): Ph-F, (B): Ph-Cl, (C): Ph-Br, (D): Ph-I$

The correct sequential addition of reagents in the preparation of $3-$nitrobenzoic acid from benzene is:

The reaction of bromobenzene with bromomethane and sodium metal in dry ether to give toluene is known as:

Arrange the following compounds in increasing order of their dipole moment:
$(I)$ Toluene
$(II)$ $m$-Dichlorobenzene
$(III)$ $o$-Dichlorobenzene
$(IV)$ $p$-Dichlorobenzene