Increasing order of electron withdrawing power of following functional groups is:
a. -CN
b. -COOH
c. -NO₂
d. -I
a. -CN
b. -COOH
c. -NO₂
d. -I
- $c<b<d<a$
- $c<a<b<d$
- $d<b<a<c$
- $a<b<c<d$
The Correct Option is C
Solution and Explanation
Step 1: Understanding the Concept:
The electron-withdrawing power of a functional group is determined by its inductive effect ($-I$ effect) and its resonance/mesomeric effect ($-M$ or $-R$ effect). Groups that have highly electronegative atoms or positive charges on the central atom are the strongest withdrawers.
Step 2: Key Formula or Approach:
1. Nitro ($-NO_2$) is one of the strongest withdrawers due to both strong $-I$ and $-R$ effects. 2. Cyano ($-CN$) follows closely behind $-NO_2$. 3. Carboxyl ($-COOH$) is weaker than $-CN$ but stronger than halogens. 4. Halogens ($-I$) are primarily $-I$ withdrawers but show $+R$ effects.
Step 3: Detailed Explanation:
1. $-NO_2$: The nitrogen atom is positively charged in resonance structures, making it extremely electron-deficient and strongly withdrawing. 2. $-CN$: The triple bond to nitrogen creates a strong dipole and allows for significant resonance withdrawal. 3. $-COOH$: The carbonyl group is withdrawing, but less so than the cyano or nitro groups. 4. $-I$: Iodine is electronegative, but it is the least electronegative of the common halogens and lacks the pi-system resonance withdrawal of the other three groups. 5. Therefore, the order is: $-I<-COOH<-CN<-NO_2$.
Step 4: Final Answer:
The increasing order is $d<b<a<c$.
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