Concept explainers
Interpretation:
The orbital picture of indole, an
The number of π electrons in indole is to be given.
The electronic relationship of indole with that of naphthalene is to be stated.
Concept introduction:
The orbital picture of a compound shows the σ bonds in a molecule along with the unhybridized p orbitals on each atom in the ring containing the electrons involved in delocalization.
To draw:
The orbital picture of indole, an aromatic heterocycle which has a benzene ring fused to a pyrrole ring.
To give:
The number of π electrons in indole.
To state:
The electronic relationship of indole with that of naphthalene.
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Chapter 15 Solutions
Organic Chemistry
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- Nicotine is a diamino compound isolated from dried tobacco leaves. Nicotine has two rings and M+=162.1157 by high-resolution mass spectrometry. Give a molecular formula for nicotine, and calculate the number of double bonds.arrow_forwardThe double bond of an enamine (alkene + amine) is much more nucleophilic than a typical alkene double bond. Assuming that the nitrogen atom in an enamine is sp2hybridized, draw an orbital picture of an enamine, and explain why the double bond is electron-rich.arrow_forwardCompound A, C8H10O, has the IR and 1H NMR spectra shown. Propose a structure consistent with the observed spectra, and label each peak in the NMR spectrum. Note that the absorption at 5.5 î disappears when D2O is added.arrow_forward
- Compound A has molecular formula C5H8Br4 but shows only one singlet in the 1H-NMR spectrum. Suggest a structure for A and explain your reasoning.arrow_forwardγ-Butyrolactone (C4H6O2, GBL) is a biologically inactive compound that is converted to the biologically active recreational drug GHB (Section 19.5) by a lactonase enzyme in the body. Since γ-butyrolactone is more fat soluble than GHB, it is more readily absorbed by tissues and thus produces a faster onset of physiological symptoms. γ-Butyrolactone shows an absorption in its IR spectrum at 1770 cm−1 and the following 1H NMR spectral data: 2.28 (multiplet, 2 H), 2.48 (triplet, 2 H), and 4.35 (triplet, 2 H) ppm. What is the structure of γ-butyrolactone?arrow_forwardCompound P has molecular formula C5H9ClO2. Deduce the structure of P from its 1H and 13C NMR spectra.arrow_forward
- 3. Cyclopropenones are described as having aromatic character. How would you account for this, given that the ring contains three π-electrons?arrow_forward3) In the mid-1930s, the German theoretical chemist Erich Hückel developed a rule that dealt with the aromaticity of various compounds, which became known as the Hückel Rule. Which (parts) of the compounds listed below are aromatic? Justify your answer based on Hückel's rule. You can treat the rings separately or together as you wish.arrow_forwardCompounds B and C are isomers with molecular formula C5H9BrO2. The 1H NMR spectrum of compounds B and C are shown below. The IR spectrum corresponding to compound B showed strong absorption bands at 1739, 1225, and 1158 cm-1, while the spectrum corresponding to compound C have strong bands at 1735, 1237, and 1182 cm-1. 1.Based on the information provided, determine the structure of compounds B and C. 2.Assign all peaks in 1H NMR spectrum of compounds B and C.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning