Indole smells terrible in high concentrations but has apleasant floral-like odor when highly diluted. Its structure isThe molecule is planar, and the nitrogen is a very weakbase, with Kp = 2 × 10-12. Explain how this informationindicates that the indole molecule is aromatic.

Huckel's rule for aromaticity: The compound must be cyclic planar geometry with (4n+2) pi electrons.…

Answered: Indole smells terrible in high…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter3: Organic Compounds: Alkanes And Their Stereochemistry

Section3.SE: Something Extra

Problem 50AP: Formaldehyde, H2C=O, is known to all biologists because of its usefulness as a tissue preservative....

See similar textbooks

Similar questions

Formaldehyde, H2C=O, is known to all biologists because of its usefulness as a tissue preservative. When pure, formaldehyde trimerizes to give trioxane, C3H6O3, which, surprisingly enough, has no carbonyl groups. Only one monobromo derivative (C3H5BrO3) of trioxane is possible. Propose a structure for trioxane.
Which of the following structures is/are not aromatic? 3 O 2 and 3 only O 1 and 3 only O 1 and 2 only O 2 only O 3 only 2. 1-
There are two C–C single bonds in penta-1,3-diyne. (a) Which of those bonds would you expect to be stronger? (b) Which of those bonds would you expect to be shorter? (c) The molecule is moderately polar, with a dipole moment of 1.37 D. In which direction would you expect the dipole moment to point? Explain. Penta-1,3-diyne
Under certain reaction conditions, 2,3-dibromobutane reacts with twoequivalents of base to give three products, each of which contains twonew π bonds. Product A has two sp hybridized carbon atoms, product Bhas one sp hybridized carbon atom, and product C has none. What arethe structures of A, B, and C?
4-Methylphenol is more acidic than ethanol (pKa 10.36 vs 16.0) , even though both contain an OH group and a methyl group. Draw the structures of the anions formed from loss of the alcoholic protons from both compounds. Use resonance to explain the difference in their respective acidities.
The pentadienyl radical, H2C“CH¬CH“CH¬CH2#, has its unpaired electron delocalized over three carbon atoms.(a) Use resonance forms to show which three carbon atoms bear the unpaired electron.(b) How many MOs are there in the molecular orbital picture of the pentadienyl radical?(c) How many nodes are there in the lowest-energy MO of the pentadienyl system? How many in the highest-energy MO?(d) Draw the MOs of the pentadienyl system in order of increasing energy. (continued)762 CHAPTER 15 Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy(e) Show how many electrons are in each MO for the pentadienyl radical (ground state).(f) Show how your molecular orbital picture agrees with the resonance picture showing delocalization of the unpairedelectron onto three carbon atoms.(g) Remove the highest-energy electron from the pentadienyl radical to give the pentadienyl cation. Which carbon atomsshare the positive charge? Does this picture agree with the resonance picture?(h) Add an…
2) State if the following compounds are aromatic, non-aromatic, or anti-aromatic. (a) S: (b) ΗΝ
Use the following spectroscopic data to work out the structure of an organic compound: Molecular formula: C3H7NO2, IR (cm): 3001, 2987, 1553 and 1387 cm*1; 1H NMR (5): 1.0 (t, 3H), 2.1 (m, 2H), and 4.4 (t, 2H); 13C NMR (5): 10, 21, and 78. MS: 89 (M+), 43 (Base peak), 41, and 29
5) Which of the following compounds is aromatic? B C H D
Which of the following species is AROMATIC? (Note all species have a planar geometry) NO CH3 1 || ||| NO CH3 IV
Which of the following structures are NOT aromatic? A B D O ZI
Dr and name all possible aromatic compounds with the formula C8H9Br (There are 14)

SEE MORE QUESTIONS

Recommended textbooks for you

Organic Chemistry

Chemistry

ISBN:

9781305080485

Author:

John E. McMurry

Publisher:

Cengage Learning

Organic Chemistry

Chemistry

ISBN:

9781305580350

Author:

William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:

Cengage Learning

Introduction to General, Organic and Biochemistry

Chemistry

ISBN:

9781285869759

Author:

Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Publisher:

Cengage Learning

Organic Chemistry

Chemistry

ISBN:

9781305080485

Author:

John E. McMurry

Publisher:

Cengage Learning

Organic Chemistry

Chemistry

ISBN:

9781305580350

Author:

William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:

Cengage Learning

Introduction to General, Organic and Biochemistry

Chemistry

ISBN:

9781285869759

Author:

Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Publisher:

Cengage Learning

SEE MORE TEXTBOOKS

Indole smells terrible in high concentrations but has a pleasant floral-like odor when highly diluted. Its structure is The molecule is planar, and the nitrogen is a very weak base, with Kp = 2 × 10-12. Explain how this information indicates that the indole molecule is aromatic.