Question

C-Cl bond in chlorobenzene. (in comparison to C-Cl bond in methyl chloride) is long & weak short & weak long & strong short & strong

Answer 1

.  In case of haloalkane, the carbon attached to halogen atom is sp3 hybridised where as in case of haloarenes, the carbon attached to halogen atom is sp2 hydridised. 
In sp2 hybridisation s character is 33 % whereas in case of sp3 hybridisation, s character is 25 %.
We know higher is the s character higher will be the electronegativity, therefore the carbon having sp2 hybridisation is more electronegative and hence the bond pair of electron would be more closer to carbon, which results in the shortening of the C-Cl bond. 

Answer 2

it is shorter and stronger bond
campare to C-Cl in Methyl chloride because the bond length of double bond is smaller than single bond
also this bond is stronger because of small size as well as the resonance stability of chloro benzene