Answer
Analysis of Each Option
-
Reduction of esters with DIBAL (Diisobutylaluminum hydride):
DIBAL can selectively reduce esters to aldehydes at low temperatures. However, with **excess** DIBAL or under modified conditions, esters may be reduced only partially, especially in bulky systems, yielding **ketones** in rare controlled cases.✔ May produce ketones under specific conditions -
Oxidation of a primary alcohol using KMnO₄:
KMnO₄ is a strong oxidizing agent and will oxidize primary alcohols all the way to **carboxylic acids**.✘ Does not yield ketones -
Oxidation of a primary alcohol using PCC (Pyridinium chlorochromate):
PCC is a mild oxidizer, converting primary alcohols to **aldehydes**, not ketones.✘ Does not yield ketones -
Oxidation of a secondary alcohol:
This is not listed, but worth noting: **secondary alcohols** are typically oxidized to **ketones** using either PCC or KMnO₄.
Final Evaluation
The only valid reaction among the listed choices that can yield a ketone—under controlled conditions—is:
✔ Reduction of esters with DIBAL
Therefore, the correct answer is:
None of these
