Consider the molecule 4-chlorobutanoic acid. On which numbered carbon atom (following IUPAC rules, w — GOC and Organic Chemistry Basics Chemistry Question
Question
Consider the molecule 4-chlorobutanoic acid. On which numbered carbon atom (following IUPAC rules, with the carboxyl carbon as C1) is the electron-withdrawing chlorine atom attached, resulting in a minimal $-I$ effect compared to its isomer, 2-chlorobutanoic acid?
Answer: 4
💡 Solution & Explanation
In 4-chlorobutanoic acid ($Cl-CH_2-CH_2-CH_2-COOH$), the carboxyl carbon is C1. Therefore, the chlorine atom is attached to carbon number 4. Due to the distance, its $-I$ effect on the acidic $-OH$ group is significantly weaker than in 2-chlorobutanoic acid.
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