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Organic Chemistry – Some Basic Principles And Techniques

Question
CBSEENCH11007555

Explain the term inductive effect. 

Solution

Whenever an electron - withdrawing atom such as halogen i.e.  - X(or a group such as nitro) is attached to the end of a carbon atom, the σ; electrons of the C – X bond are displaced towards the more electronegative halogen atom. As a result, the atom X acquires a partial negative charge (δ–). C1 on the other hand acquires a partial positive charge (δ+). The C1 –X bond thus becomes a polar bond.
straight delta apostrophe apostrophe apostrophe space plus space straight delta apostrophe apostrophe space plus space straight delta apostrophe space plus space straight delta space plus space straight delta minus
straight C subscript 4 space minus space straight C subscript 3 space minus space straight C subscript 2 space minus space straight C subscript 1 space rightwards harpoon with barb upwards space straight X
The partial positive charge on C1, in turn, attracts, the σ;-electrons, of the C1 – C2 bond towards it. As a result, C2 acquires a partial positive charge (i.e. δ'+ ), of course, smaller than that of C1. Similarly, C3 will acquire a small positive charge (δ"+ ) that will still be smaller than that on C2. Thus, positive charge (δ"+ ) that will still be smaller than that on C2. Thus, positive charge (δ"+ ) that will still be smaller than that on C2
straight delta to the power of plus space greater than space straight delta apostrophe space plus space greater than space straight delta apostrophe apostrophe plus
This permanent displacement of electrons along the chain of carbon atoms due to the presence of an atom or group of different electronegativity at the end of the carbon atom is called inductive effect or I-effect. It is represented by an arrow as shown below:
negative straight C subscript 4 minus straight C subscript 3 minus straight C subscript 2 minus straight C subscript 1 minus straight X
The atom X exerts an inductive effect only up to a certain length of the chain depending upon its electronegativity. Beyond that, the effect disappears. For practical purposes, it is ignored after the third atom.

The inductive effect is also called transmission effect (T-effect) because the polarity is transmitted along the carbon atom chain.
Types of Inductive effect. It is of two types:
(i) - I effect (Electron withdrawing inductive effect). If the substituent attached to the end of the carbon chain is electron withdrawing, the effect is called - I effect. For example,
straight delta apostrophe apostrophe space plus space straight delta apostrophe space plus space straight delta space plus space straight delta minus
minus straight C minus straight C minus straight C minus straight X left parenthesis negative straight I space effect right parenthesis
The decreasing order of -I effect of some common groups is as follows:
negative NO subscript 2 greater than negative SO subscript 3 straight H greater than negative CN greater than negative COOH greater than negative straight F greater than Cl
greater than negative Br space greater than space minus space straight I thin space greater than space minus space OC subscript 6 straight H subscript 5 space greater than space minus COOR greater than space minus space OR greater than
minus OH greater than space minus space straight C subscript 6 straight H subscript 6 greater than space minus space straight H
(ii) + I effect (Electron releasing inductive effect). If the substituent attached to the end of the carbon chain is electron donating, the effect is called +I effect. For example. 
straight delta apostrophe space minus space straight delta apostrophe space space space space straight delta apostrophe
straight C space minus space straight C space minus space straight C space minus space CH subscript 3 space left parenthesis plus straight I space effect right parenthesis
The decreasing order of some groups having +I effect is as follows:
left parenthesis CH subscript 3 right parenthesis subscript 3 straight C space minus space greater than left parenthesis CH subscript 3 right parenthesis subscript 2 space CH space minus space greater than space CH subscript 3 space minus space CH subscript 2 space minus space CH subscript 2 space minus space
space space space space space space space space space space space space space space space space space space space space space space space space space space space space space space space space space space space space space space space space space space minus greater than CH subscript 3 space minus space CH subscript 2 space minus greater than negative CH subscript 3 greater than negative straight H