Both the acetamido (-NHCOCH3) and bromo (-Br) substituents are ortho, para directors. Even though the acetamido group is much la
rger than the bromo group, the -Cl is still introduced next to the acetamido group in spite of the greater steric hinderance at this site. Why?
1 answer:
Answer:
Explanation has been given below
Explanation:
- Attachment of -Cl group at ortho position to acetamido group can be explained in terms of hydrogen bonding formation.
- A hydrogen bonding can be formed between proton attached with N atom in acetamido group and Cl atom at ortho position. This leads to a formation of a stable 5-membered ring structure.
- Hence ortho substitution by Cl is favorable process.
- There is no hydrogen bonding possible between Br and Cl atom in ortho position. Therefore Cl prefers para position to avoid steric hindrance.
- Structure of hydrogen bonded structure has been shown below.
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