Carboxylic Acid and Acid DerivativesMedium

Question

Given below are two statements:

Statement-I: Oxidation of p-nitrotoluene with acidic ${KMnO}_{4}$ gives an acid that is stronger than benzoic acid.

Statement-II: Reduction of p-nitrotoluene with Sn/HCl followed by neutralization gives an amine that is more basic than aniline.

In light of the above statements, choose the most appropriate answer from the options given below.

Options

A.Statement-I is correct but Statement-II is incorrect
B.Statement-I is incorrect but Statement-II is correct
C.Both Statement-I and Statement-II are correct
D.Both Statement-I and Statement-II are incorrect

Solution

Sol. [Key Concept: Oxidation of substituted toluenes]

• Oxidation of p-nitrotoluene with acidic ${KMnO}_{4}$ converts into p-nitrobenzoic acid.

because of -I effect and -M effect, making p-nitrobenzoic acid as stronger acid than benzoic acid.

- Reduction of p-nitrotoluene with Sn/HCl followed by neutralization reduces the $\left( - {NO}_{2} \right)$ to an amino group $\left( - {NH}_{2} \right)$, forming p-toluidine.

i.e., p -methylaniline is more basic than aniline due to the +I effect and hyperconjugation.

Create a free account to view solution

View Solution Free
Topic: Carboxylic Acid and Acid Derivatives·Practice all Carboxylic Acid and Acid Derivatives questions

More Carboxylic Acid and Acid Derivatives Questions

Hydrolysis of 1,1, 1-trichloro derivative (A) of alkane gives a molecule (B) on alkaline hydrolysis which produces red c...Among the following the stringest acid is...Action of acetylene on dilute H2SO4 gives...Which of the following diazonium salt is relatively stable at 0-5oC:...The reaction , CH3COOC2H5 C2H5OH + CH3CH2OH, is called -...