Does intramolecular hydrogen bonding influence effective polarity of compound for liquid chromatogra

[TomBombadil14]

Hi! Confused about #21 EK FL2 C/P -

Does intramolecular hydrogen bonding affect the polarity of a total molecule?

In the problem, there are two compounds. Compound 1 has a hydroxyl and carbonyl oxygen (from ketone) adjacent to each other. Compound 2 has two carbonyl oxygens (from ketones) adjacent to each other. The question wants to know which will elute first with the polar mobile phase. I know alcohol groups are more polar than ketones, but does intramolecular H bonding with the -OH and =O affect polarity at all?

---

Members don't see this ad.

 

[aldol16]

The silica will compete for the hydrogen bond and since silica is a strongly hydrogen-bonding substance, it will win.