Ans 1... I feel... II > IV > I > III ..btw i have encountered the same question in the SQB Of BT insti...and the options given were
A - I < II < III < IV
B- IV < III < II < I
C- IV < I < II < III
D- III < II < IV < I
since we know that in pyrole the lone pair of N are in conjugation with the ring..so it's gonna be least basic so on that basis answer is D
Ans 2 ...Wen Cl atom leaves..carbocation is formed and the ring attains aromaticity due to which it becomes very∞ stable....even 1014 stable than the triphenyl carbocation Ph3C+ ...
Ans3..this one has been discussed here b4..the basic funda of doing this question is to separate the charges and then if the charges are stabalised due to any reason(in this case the reason is aromaticity) then the compound will have dipole momment...
btw the link is :
http://www.targetiit.com/iit-jee-forum/posts/organic-13833.html
Ans 4 ...the topmost COOH grp will be ionised first then the bottom most COOH grp and then the middle one...the reason why i placed the middle one at last is coz the way eure has drawn the diagram there can be a possibility of hydrogen bonding with the fluorine atom...just a guess