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Dichloroethylene \(\left(\mathrm{C}_{2} \mathrm{H}_{2} \mathrm{Cl}_{2}\right)\) has three forms (isomers), each of which is a different substance. (a) Draw Lewis structures of the three isomers, all of which have a carbon-carbon double bond. (b) Which of these isomers has a zero dipole moment? (c) How many isomeric forms can chloroethylene, \(\mathrm{C}_{2} \mathrm{H}_{3} \mathrm{Cl}\), have? Would they be expected to have dipole moments?

Short Answer

Expert verified
Dichloroethylene (C2H2Cl2) has three isomers, of which 1,1-Dichloroethylene and trans-1,2-Dichloroethylene have a zero dipole moment. Chloroethylene (C2H3Cl) has two possible isomeric forms: vinyl chloride (H2C=CH-Cl) and chloroethene (Cl-C=C-H). Both Chloroethylene isomers have nonzero dipole moments due to the electronegativity difference between Cl and C, with no other atoms canceling them out.

Step by step solution

01

Lewis structures of Dichloroethylene (C2H2Cl2) isomers

First, let's draw the Lewis structures for the three possible isomers of dichloroethylene (C2H2Cl2), having a carbon-carbon double bond. Isomer 1 (1,1-Dichloroethylene): ``` Cl Cl | | H-C=C-H or H-C=C-Cl ``` Isomer 2 (cis-1,2-Dichloroethylene): ``` Cl H | | H-C=C-Cl or H-C=C-H ``` Isomer 3 (trans-1,2-Dichloroethylene): ``` Cl Cl | | H-C=C-H or H-C=C-Cl ```
02

Determining Isomer with Zero Dipole Moment

To figure out which isomer has a zero dipole moment, let's compare the dipole vectors for the three isomers. In the 1,1-Dichloroethylene isomer, the two C-Cl bonds have dipole moments that point in opposite directions (towards the more electronegative Cl), canceling each other out, giving a zero net dipole moment. cis-1,2-Dichloroethylene has the Cl atoms on the same side of the double bond. This makes the molecule's dipole moments not cancel each other out, producing a nonzero net dipole moment. In trans-1,2-Dichloroethylene, the two C-Cl bonds are on opposite sides of the double bond, which makes their dipole moments cancel each other out, resulting in a zero net dipole moment. Thus, 1,1-Dichloroethylene and trans-1,2-Dichloroethylene isomers have a zero dipole moment.
03

Chloroethylene (C2H3Cl) Isomers and Their Dipole Moments

Now let's analyze Chloroethylene (C2H3Cl) for its possible isomeric forms. There are two possible isomers for Chloroethylene: Isomer 1 (vinyl chloride or H2C=CH-Cl): ``` Cl H | | H-C=C-H or H-C=C-H ``` Isomer 2 (chloroethene or Cl-C=C-H): ``` Cl Cl | | H-C=C-H or H-C=C-Cl ``` Both isomers have a net dipole moment, nonzero, as the C-Cl bond creates a dipole due to the electronegativity difference between Cl and C, and no other atoms cancel it out. So yes, they would be expected to have dipole moments.

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