Question:
Which of the following does not form benzoic acid on oxidation with alkaline \(KMnO_4\) followed by acidification?
Which of the following does not form benzoic acid on oxidation with alkaline \(KMnO_4\) followed by acidification?
Show Hint
Benzylic hydrogen is essential for side-chain oxidation of alkyl benzenes using \(KMnO_4\).
Updated On: Aug 13, 2026
- 1-phenylpropane
- 2-phenylpropane
- Acetophenone
- 2-methyl-2-phenylpropane
Show Solution
Verified By Collegedunia
The Correct Option is D
Solution and Explanation
Concept:
Alkaline \(KMnO_4\) oxidizes alkyl side chains of benzene to \(-COOH\) group only if at least one benzylic hydrogen is present.
Step 1: Check benzylic hydrogen presence.
(A) 1-phenylpropane (\(Ph-CH_2-CH_2-CH_3\)) → has benzylic H → forms benzoic acid.
(B) 2-phenylpropane (\(Ph-CH(CH_3)_2\)) → has benzylic H → forms benzoic acid.
(C) Acetophenone (\(Ph-CO-CH_3\)) → side chain oxidizes to benzoic acid.
(D) 2-methyl-2-phenylpropane (\(Ph-C(CH_3)_3\)) → no benzylic hydrogen → no oxidation to benzoic acid.
Step 2: Conclusion.
Only (D) does not form benzoic acid. \[ \boxed{\text{2-methyl-2-phenylpropane}} \]
Step 1: Check benzylic hydrogen presence.
(A) 1-phenylpropane (\(Ph-CH_2-CH_2-CH_3\)) → has benzylic H → forms benzoic acid.
(B) 2-phenylpropane (\(Ph-CH(CH_3)_2\)) → has benzylic H → forms benzoic acid.
(C) Acetophenone (\(Ph-CO-CH_3\)) → side chain oxidizes to benzoic acid.
(D) 2-methyl-2-phenylpropane (\(Ph-C(CH_3)_3\)) → no benzylic hydrogen → no oxidation to benzoic acid.
Step 2: Conclusion.
Only (D) does not form benzoic acid. \[ \boxed{\text{2-methyl-2-phenylpropane}} \]
Was this answer helpful?
5
0
Top AP EAPCET Chemistry Questions
- The four quantum numbers of the valence electron of potassium are :
- The volume of $0.02\, M$ acidified permanganate solution required for complete reaction of $60\, mL$ of $0.01\, MI^{-}$ ion solution to form $I_2$ in $mL$ is
- In which of the following the election gain enthalpy of elements is correctly arranged?
- The radii of $ \text{F,}{{\text{F}}^{-}}\text{O} $ and $ {{\text{O}}^{2-}} $ are in the order
- Which of the following has the highest first ionization potential?
View More Questions
Top AP EAPCET Organic Chemistry Questions
- Number of deactivating groups among: \( -Cl, -SO_3H, -OH, -NHC_2H_5, -COOCH_3, -CH_3 \)
- What are \( X \) and \( Y \) respectively in the following reaction sequence?
- An alcohol \( X \) (\( C_4H_{10}O \)) does not give turbidity with conc. HCl and ZnCl\(_2\) at room temperature. \( X \) on reaction with reagent \( Y \) gives \( Z \). What are \( X \), \( Y \), and \( Z \) respectively?
Which of the following sets of reagents convert toluene to benzaldehyde?
What are X and Y respectively in the following reactions?
View More Questions
Top AP EAPCET Questions
- A body is projected from the ground at an angle of $\tan^{-1} \left( \frac{8}{7}\right)$ with the horizontal. The ratio of the maximum height attained by it to its range is
- The four quantum numbers of the valence electron of potassium are :
- A lens forms real and virtual images of an object, when the object is at $u_{1}$ and $u_{2}$ distances respectively. If the size of the virtual image is double that of the real image, then the focal length of the lens is (take, the magnification of the real image as $m$ )
- Two spheres $P$ and $Q$, each of mass $200\, g$ are attached to a string of length one metre as shown in the figure. The string and the spheres are then whirled in a horizontal circle about $O$ at a constant angular speed. The ratio of the tension in the string between $P$ and $Q$ to that of between $P$ and $O$ is $(P$ is at mid-point of the line joining $O$ and $Q$ )
- The volume of $0.02\, M$ acidified permanganate solution required for complete reaction of $60\, mL$ of $0.01\, MI^{-}$ ion solution to form $I_2$ in $mL$ is
View More Questions