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Organic Chemistry: Some Basic Principles and Techniques — Chemistry STD 11 Science — Question

Rajasthan BoardEnglish MediumSTD 11 ScienceChemistryOrganic Chemistry: Some Basic Principles and Techniques5 Marks
Question
Explain the terms Inductive and Electromeric effects. Which electron displacement effect explains the following correct orders of acidity of the carboxylic acids?
  1. Cl3CCOOH > Cl2CHCOOH > ClCH2COOH.
  2. CH3CH2COOH > (CH3)2CHCOOH > (CH3)3C.COOH.
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Answer

Inductive Effect: The inductive effect refers to the polarity produced in a molecule as a result of higher electronegativity of one atom compared to another.Atoms or groups which lose electron towards a carbon atom are said to have +1 Effect.

Those atoms or groups which draw electron away from a carbon atom are said to have -I Effect.

Common examples of -I effect are:

NO2, F, Cl, Br, I, OH etc.

Examples of +1 effect are (Electron releasing)

(CH3)2C- , (CH3)2CH-, CH3CH2- CH3- etc.

Electromeric effect: The electromeric effect refers to the polarity produced in a multiple bonded compound as it is approached by a reagent.

The atom A has lost its share in the electron pair and B has gained this share.

As a result A acquires a positive charge and B a negative charge. It is a temporary effect and takes place only in the presence of a reagent.

  1. -I-effect as shown below: As the number of halogen atoms decreases, the overall -I- effect decreases and the acid strength decreases accordingly.

  1. +I-effect as shown below: As the number of alkyl groups increases, the +I-effect increases and the acid strength decreases accordingly.

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  1. Arrange the following according to given property

$\text{CH}_3\stackrel{\oplus \ \ \ }{\text{CH}}_2,\text{C}_6\text{H}_5-\stackrel{\oplus\ \ \ \ }{\text{CH}}_2,(\text{CH}_3)_3\stackrel{\oplus \ \ \ \ }{\text{CH}},$

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  1. $\text{HC}\equiv\text{C}^{\ominus},\text{Ch}_2=\stackrel{\ominus\ \ \ \ \ \ }{\text{CH}_2},\text{CH}_3-\stackrel{\ominus\ \ \ \ \ }{\text{CH}_2},\stackrel{\ominus \ \ \ \ \ }{\text{CH}_3}$ (increasing order of stabillity)

  2. $\text{C}_6\text{H}_5\stackrel{\bf. \ \ \ \ }{\text{CHCH}_3},\text{C}_6\text{H}_5\text{CH}_2\stackrel{\bf.\ \ \ \ \ }{\text{CH}_2},\text{C}_6\text{H}_5\stackrel{\bf.}{\text{C}}_3(\text{CH}_3)_2$ (increasing order of stabillity)

  3. $\text{CH}_3-\stackrel{\oplus \ \ \ \ }{\text{CH}}-\text{O}-\text{CH}_3,\text{CH}_3-\stackrel{\oplus \ \ \ \ }{\text{CH}},-\text{OCH}_3,$

${\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{O}}\\{\ \ \ \ \ \ \ \\ \ \ \ \ \ \ \ \ \ \ \ \ \ \\ \|}\\\ \text{CH}_3-\stackrel{\oplus \ \ \ \ }{\text{CH}}\text{C}-\text{OCH}_3$ (decreasing order of stability)

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