Reactions of Chromones, Chemistry tutorial

Introduction:

Chromone (or 1,4-benzopyrone) is the derivative of benzopyran having a substituted keto group on the pyran ring. The derivatives of Chromone are collectively termed as Chromones. Most, although not all, Chromones are as well phenylpropanoids.

General Chemical reactions of Chromones:

Chromones vary marginally in their chemistry from Coumarins (benzopyran-2-ones) as the carbonyl group is now conjugated by the oxygen atom through the double bond of the heterocycle. This conjugation doesn't involve the benzene ring (figure shown below).

917_Chromone Conjugation.jpg

Fig: Chromone Conjugation

As a result, the Chromones are instead more basic and strong acids readily protonate the carbonyl oxygen atoms, making crystalline benzopyrilium salts. Once protonated, the molecule must be resistant to further electrophilic attack, however by fuming nitric acid and concentrated sulphuric acid at between 0°C and room temperature, Chromone provides the 6-nitro derivative (figure shown below). Chromone as well undergoes a Mannish-type reaction (figure shown below) with dimethylamine and formaldehyde (methanal) in hydrogen chloride and ethanol; here the product is 3-(N-N-dimethylaminomethyl) Chromone.

1717_Reaction of Chromones.jpg

Fig: Reaction of Chromones

Comparatively hard nucleophiles, like Grignard reagents, might attack at the carbonyl carbon, while softer nucleophiles, example: hydroxide ion, join at C-2 by conjugative addition, and this might then cause ring opening (figure shown below).

2263_Reactions of Chromones with Nucleophiles.jpg

Fig: Reactions of Chromones with Nucleophiles

Tutorsglobe: A way to secure high grade in your curriculum (Online Tutoring)

Expand your confidence, grow study skills and improve your grades.

Since 2009, Tutorsglobe has proactively helped millions of students to get better grades in school, college or university and score well in competitive tests with live, one-on-one online tutoring.

Using an advanced developed tutoring system providing little or no wait time, the students are connected on-demand with an expert at www.tutorsglobe.com. Students work one-on-one, in real-time with a tutor, communicating and studying using a virtual whiteboard technology.  Scientific and mathematical notation, symbols, geometric figures, graphing and freehand drawing can be rendered quickly and easily in the advanced whiteboard.

Free to know our price and packages for online chemistry tutoring. Chat with us or submit request at info@tutorsglobe.com