Compound A reacts with both PCC and H2CrO4 to give the same oxygen containing product.

Compound A is:

Question

Compound A reacts with both PCC and H2CrO4 to give the same oxygen containing product.

Compound A is:

BlackTom AI · Accepted Answer

To determine which starting functional group in Compound A leads to the same oxygen-containing product when treated with both PCC and H2CrO4, we need to consider what each oxidizing agent does.
Option 1: an aldehyde. If A were an aldehyde (or if oxidation produced an aldehyde), PCC would not be relevant here since PCC oxidizes alcohols, not aldehydes. More importantly, primary alcohols oxidized by PCC give aldehydes, while Jones (H2CrO4) oxidation would further oxidize that aldehyde to a carboxylic acid. Thus, the two reagents would not yield the same product. This option is inconsistent with the premise.
Option 2: a tertiary alcohol. Tertiary alcohols resist oxidation by PCC and are generally resistant to oxidation by aqueous chromic acid under typical conditions; they do not form a simple ketone or aldehyde as a product. Therefore, this choice cannot explain the same product from both oxidants.
Option 3: a primary alcohol. PCC would oxidize a primary alcohol to an aldehyde, whereas H2CrO4 would typically oxidize a primary alcohol all the way to a carboxylic acid. The two products (aldehyde vs carboxylic acid) would differ, so this option is untenable.
Option 4: a secondary alcohol. This is the scenario that fits: PCC oxidizes a secondary alcohol to a ketone, and hot, strong oxidants like H2CrO4 also oxidize a secondary alcohol to a ketone. In this case, both reagents produce the same oxygen-containing product (a ketone). This aligns with the statement that both reagents give the same product and is consistent with standard oxidation chemistry of secondary alcohols.
Putting it together, only the secondary alcohol option provides a consistent pathway where PCC and H2CrO4 yield the same oxidation product, namely a ketone.

CHEM 110 Lecture Quiz Week 7

Compound A reacts with both PCC and H2CrO4 to give the same oxygen containing product. Compound A is:

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