As someone in the teaching profession, my experience is that most instructors are happy when a student understands the content at a level high enough to catch mistakes. The halide ions, which are electron-withdrawing but ortho, para directing, are the exception. It could be an honest mistake in the wording of the question. Ortho, para directing groups are electron-donating groups meta directing groups are electron-withdrawing groups. It would be worth contacting your instructor and asking for clarification, noting that these are not examples of any kind of stereoisomerism. The two main types of stereoisomerism are enatiomerism and diastereomerism. Constitutional isomerism is not a type of stereoisomerism. The orthosubstituted cationic intermediate can even be favored over both meta and para if the electronwithdrawing character is sufficient to favor ortho over. So, what then are the relationships between these three compounds? Let's look at a decision flowchart for relationship between structures: All isomers require bond-breaking to interconvert. Not that the qualifying text about having to break bonds to interconvert is unhelpful and irrelevant. The (1,2), (1,3), and (1,4) in the names of these compounds indicate that this is not the case. Historically, p -DCB is also known as PDB. Stereoisomers have the same connectivity of atoms (constitution) with different arrangement in space. Ortho-, meta-, and para -dichlorobenzene (1,2-dichlorobenzene, 1,3-dichloro-benzene, 1,4-dichlorobenzene, respectively) are also called o -DCB, m -DCB, and p -DCB. These compounds do not have a stereochemical relationship.
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