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1

I read up in my text book that dipole moment direction of phenol is towards OH group so I guess O being highly electronegative pulls the electrons more and participates less in resonance hence it has deta negative charge on it thus acc to convention dipole moment direction is from positive to negative hence direction is towards OH group.


1

I would say that your analysis of first, second and fourth one is correct, as H-bonds are stronger than dipole-dipole interactions. However, you made a mistake while filtering compounds having dipole-dipole interaction. The $1$ and $3$, both have dipoles! The $\ce{C=O}$ bonds in $\ce{CO2}$ are polar and hence they possess dipoles, but unlike a water molecule,...


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