Of the compounds which correspond to the general name "dichlorocyclobutane," how many are optically active?

Question

Quizplus · Accepted Answer

Dichlorocyclobutane can exist in three different isomeric forms when considering optical activity: 1,2-dichlorocyclobutane, which has no chiral centers and thus is not optically active; 1,3-dichlorocyclobutane, which also has no chiral centers and is not optically active; and 1,1-dichlorocyclobutane, which is not considered because it doesn't lead to optical isomers. The only form that can exhibit optical activity is 1,2-dichlorocyclobutane when the two chlorine atoms are on adjacent carbons in a cis configuration, creating a chiral center. However, my explanation mistakenly suggested this configuration leads to optical activity, which it does not due to the molecule's symmetry. The correct interpretation is that for a molecule to be optically active, it must lack an internal plane of symmetry and have chiral centers. In the case of dichlorocyclobutanes, the configurations that could potentially lead to optical activity do not meet these criteria adequately to produce optically active isomers. Therefore, the correct answer reflects the understanding that no dichlorocyclobutane configurations result in optical activity due to the symmetry and lack of chiral centers in the relevant configurations.

Of the Compounds Which Correspond to the General Name "Dichlorocyclobutane