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NEET 2007
Exam
NEET
Year
2007
Subject
Chemistry
Chapter
General Organic Chemistry

NEET 2007 · Chemistry · General Organic Chemistry

Which of the following represents the correct order of the acidity...

Which of the following represents the correct order of the acidity in the given compounds?

Options

  1. AFCH2COOH>CH2COOH>BrCH2COOH>ClCH2COOH\mathrm{FCH}_2 \mathrm{COOH}>\mathrm{CH}_2 \mathrm{COOH}> \mathrm{BrCH}_2 \mathrm{COOH}>\mathrm{ClCH}_2 \mathrm{COOH}
  2. BBrCH2COOH>ClCH2COOH>FCH2COOH>CH3COOH\mathrm{BrCH}_2 \mathrm{COOH}>\mathrm{ClCH}_2 \mathrm{COOH}> \mathrm{FCH}_2 \mathrm{COOH}>\mathrm{CH}_3 \mathrm{COOH}
  3. CFCH2COOH>ClCH2COOH>BrCH22COOH>CH3COOH\mathrm{FCH}_2 \mathrm{COOH}>\mathrm{ClCH}_2 \mathrm{COOH}> \mathrm{BrCH}_2^2 \mathrm{COOH}>\mathrm{CH}_3 \mathrm{COOH}
  4. DCH3COOH>BrCH2COOH>ClCH2COOH>FCH2COOH\mathrm{CH}_3 \mathrm{COOH}>\mathrm{BrCH}_2 \mathrm{COOH}> \mathrm{ClCH}_2 \mathrm{COOH}>\mathrm{FCH}_2 \mathrm{COOH}

Correct answer

A. FCH2COOH>CH2COOH>BrCH2COOH>ClCH2COOH\mathrm{FCH}_2 \mathrm{COOH}>\mathrm{CH}_2 \mathrm{COOH}> \mathrm{BrCH}_2 \mathrm{COOH}>\mathrm{ClCH}_2 \mathrm{COOH}

Step-by-step solution

Electron withdrawing substituent increases the acidity by increasing the ionic character of −OH-\mathrm{OH} by inductive effect. Electronegativity decreases in the order. F>Cl>Br\mathrm{F}>\mathrm{Cl}>\mathrm{Br} -I effect also decreases in the same order. Thus, the correct sequence is FCH2COOH>ClCH2COOH>BrCH2COOH>CH3COOH\begin{aligned} & \mathrm{FCH}_2 \mathrm{COOH}>\mathrm{ClCH}_2 \mathrm{COOH}> \\ & \mathrm{BrCH}_2 \mathrm{COOH}>\mathrm{CH}_3 \mathrm{COOH} \end{aligned} Related Theory I effect is a permanent effect & generally represented by an arrow on the bond.
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