Concept explainers
(a) In 1960 T. Katz (Columbia University) showed that cyclooctatetraene adds two electrons when treated with potassium metal and forms a stable, planar dianion,
Use the molecular orbital diagram given in Fig. 14.7 and explain this result.
(b) In 1964 Katz also showed that removing two protons from the compound below (using butyllithium as the base) leads to the forma-tion of a stable dianion with the formula
Propose a reasonable structure for the product and explain why it is stable.
Want to see the full answer?
Check out a sample textbook solutionChapter 14 Solutions
Organic Chemistry
Additional Science Textbook Solutions
Chemistry: Structure and Properties (2nd Edition)
General, Organic, and Biological Chemistry (3rd Edition)
Chemistry
Inorganic Chemistry
The Organic Chem Lab Survival Manual: A Student's Guide to Techniques
Basic Chemistry (5th Edition)
- Azulene, an isomer of naphthalene, has a remarkably large dipole moment for a hydrocarbon (µ = 1.0 D). Explain using resonance structures.arrow_forwardThe enamine prepared from acetone and dimethylamine is shown here in its lowest-energy form. (a) What is the geometry and hybridization of the nitrogen atom? (b) What orbital on nitrogen holds the lone pair of electrons? (c) What is the geometric relationship between the p orbitals of the double bond and the nitrogen orbital that holds the lone pair? Why do you think this geometry represents the minimum energy?arrow_forwardPredict how the bond, shown in each of the following compounds will break with the aidof the appropriate arrow(s). Also give the structure(s) of the species formed in eachreaction.(a) CH3── I →(b) Q ── Q →arrow_forward
- Draw a resonance structure of the acetonitrile anion, :CH2C =N, and account for the acidity of nitriles.arrow_forwardThere are several isomeric alkanes of molecular formula C6H14.Two of these exhibit the following 1H-NMR spectra. Propose a structure for each of the isomers. Isomer A: δ = 0.84 (d, 12 H), 1.39 (septet, 2H) ppm Isomer B: δ = 0.84 (t, 3 H), 0.86 (s, 9H), 1.22 (q, 2H) ppmarrow_forward7aarrow_forward
- Give reasons for the following :(i) Ethyl iodide undergoes SN2 reaction faster than ethyl bromide.(ii) (±) 2-Butanol is optically inactive.(iii) C—X bond length in halobenzene is smaller than C—X bond length in CH3—X.arrow_forwardSuggest a possible structure for Compound X.arrow_forwardDraw the structure of the predominant form of CF3CH2OH (pK a = 12.4) at pH = 6.arrow_forward
- (a) Write the products of following reactions. Give mechanism with proper stereochemistry? (2 x 2.5 = 5) (ii) Me Δ Δ CNarrow_forwardGive the reduction organic products of the following organic molecules (shown below) treated by sodium borohydride (NaBH4) in aqueous acidic solution of hydrochloric acid. (1) 0 (2) OH LOHarrow_forwardEach of the following reactions has been described in the chemical literature and involves an organic reactant somewhat more complex than those we have encountered so far. Nevertheless, on the basis of the topics covered in this chapter, you should be able to write the structure of the principal organic product of each reaction.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning