Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 27: Problem 651

Many of the beautiful colors of butterflies' wings, autumn leaves, and flowers are due to the presence of flavone derivatives called anthocyanins. When anthocyanins are hydrolyzed in hydrochloric acid (to remove sugar residues), they produce aromatic oxygen-containing salts. One of these is delphinidin chloride. Explain why delphinidin chloride is aromatic. What is the hybridization of the heterocyclic oxygen in this compound?

Short Answer

Expert verified
Delphinidin chloride is aromatic because it meets all four criteria of aromaticity: it is cyclic, planar, contains 10 π-electrons (which fits the 4n+2 rule with n=2), and all atoms in the ring system are conjugated. The heterocyclic oxygen in delphinidin chloride is sp2 hybridized as it forms a double bond and a single bond within the conjugated ring system.

Step by step solution

01

Determine if delphinidin chloride is cyclic

Delphinidin chloride, with the chemical formula C_15H_11O_6Cl, contains a cyclic structure with double bonds and a heterocyclic oxygen atom. This satisfies the first criterion for aromaticity.
02

Determine if delphinidin chloride is planar

In delphinidin chloride, all the carbon and oxygen atoms in the ring are sp2 hybridized, which means they all have planar geometry. This satisfies the second criterion for aromaticity.
03

Determine if delphinidin chloride contains (4n + 2) π-electrons

Counting the number of π-electrons in the delphinidin chloride cyclic structure, there are a total of 10 π-electrons, which can be represented as 4n + 2 when n=2. This satisfies the third criterion for aromaticity.
04

Check for conjugation

All atoms in the ring system have p-orbitals overlapping by a conjugation system allowing for electron delocalization. This satisfies the fourth criterion for aromaticity. Having satisfied all four criteria of aromaticity, it can be concluded that delphinidin chloride is aromatic.
05

Determine the hybridization of the heterocyclic oxygen

In delphinidin chloride, the heterocyclic oxygen is involved in the conjugated ring system and forms a double bond as well as a single bond. Thus, the heterocyclic oxygen is sp2 hybridized. In conclusion, delphinidin chloride is an aromatic compound, and the heterocyclic oxygen in this compound is sp2 hybridized.

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Start your free trial

Over 30 million students worldwide already upgrade their learning with Vaia!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

Pyridine methochloride is converted by aqueous alkali and a mild oxidizing agent (ferricyanide) to a solid compound of formula \(\mathrm{C}_{6} \mathrm{H}_{7} \mathrm{NO}\), which shows no hydroxyl absorption in the infrared. What is a likely structure for this substance and how is it formed? Would you expect a similar reaction with pyridine?

The alkaloid hygrine is found in the coca plant. Suggest a structure for it on the basis of the following evidence: Hygrine \(\left(\mathrm{C}_{8} \mathrm{H}_{1}{ }_{5} \mathrm{ON}\right)\) is insoluble in aqueous \(\mathrm{NaOH}\) but soluble in aqueous HC1. It does not react with benzenesulfonyl chloride. It reacts with phenylhydrazine to yield a phenylhydrazone. It reacts with NaOI to yield a yellow precipitate and a carboxylic acid \(\left(\mathrm{C}_{7} \mathrm{H}_{13} \mathrm{O}_{2} \mathrm{~N}\right)\). Vigorous oxidation by \(\mathrm{CrO}_{3}\) converts hygrine into hygrimic acid \(\left(\mathrm{C}_{6} \mathrm{H}_{11} \mathrm{O}_{2} \mathrm{~N}\right)\)

Two mechanisms for the Skraup synthesis are: 1 2. c1ccc2ccccc2c1 Devise an experiment whereby we can tell which is the actual mechanism.
See all solutions

Recommended explanations on Chemistry Textbooks

Physical Chemistry

Read Explanation

Inorganic Chemistry

Read Explanation

Ionic and Molecular Compounds

Read Explanation

Nuclear Chemistry

Read Explanation

Chemical Reactions

Read Explanation

Kinetics

Read Explanation
View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.

Sign-up for free