(Polar molecules, Non-polar molecules, etc.)
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The dipole moment for 1 would be the largest because the C-Cl bond vectors are pointing most nearly in the same direction in 1 whereas in 2 the C-Cl vectors point more away from each other, giving a larger cancellation of dipole.
Yes, option 1 has the largest dipole moment because the two dipoles are closer together and are separated by a smaller angle. An easy way to think about this is to think to imagine that if the dipoles were on opposite sides, they would be more likely to cancel out and would not be as strong of a dipole moment.
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