Concept explainers
Open the molecular model file for benzyne and examine the following molecular orbitals: the LUMO (lowest unoccupied molecular orbital), the HOMO (highest occupied molecular orbital), the HOMO-1 (next lower energy orbital), the HOMO-2 (next lower in energy), and the HOMO-3 (next lower in energy).
(a) Which orbital best represents the region where electrons of the additional πp bond in benzyne would be found?
(b) Which orbital would accept electrons from a Lewis base on nucleophilic addition to benzyne?
(c) Which orbitals are associated with the six
Want to see the full answer?
Check out a sample textbook solutionChapter 15 Solutions
Organic Chemistry
Additional Science Textbook Solutions
Chemistry: An Introduction to General, Organic, and Biological Chemistry (12th Edition) - Standalone book
Chemistry & Chemical Reactivity
Introductory Chemistry (5th Edition) (Standalone Book)
Organic Chemistry
Chemistry: Structure and Properties (2nd Edition)
Chemistry: A Molecular Approach (4th Edition)
- Five-membered aromatic heterocycles with one heteroatom undergo electrophilic substitutions preferentially at the α-position (C-2 and C-5) rather than at the β-position (C-3 and C-4). Explain?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_forwardAs the extent of electron delocalization into the ring increases, the geometry at nitrogen flattens. p-Nitroaniline, for example, is planar. Write a resonance contributor for p-nitroaniline that shows how the nitro group increases electron delocalization.arrow_forward
- What is the best way to draw a molecular orbital diagram for 1,3-cyclopentadiene, identifying the Lowest unoccupied molecular orbital and the highest occupied molecular orbital?arrow_forwardPredict the electronic configurations of (a) the benzeneanion, (b) the benzene cation. Estimate the π-bond energy in each case.arrow_forwardTo be aromatic, a molecule must have 4n + 2 πs electrons and must have a planar, monocyclic system of conjugation. Cyclodecapentaene fulfills one of these criteria but not the other and has resisted all attempts at synthesis. Explain.arrow_forward
- Would you expect the substituent N+(CH3)3 to more closely resemble N..(CH3)2 or-NO2 in its effect on rate and regioselectivity in electrophilic aromatic substitution? Why?arrow_forwardFor each of the following, write the major product(s) and then draw out each step in the mechanism using curved arrows. Show ALL lone pair electrons and formal charges. Redraw ALL molecules as to show explicitly ALL bonds being broken or formed. Identify the molecular orbital (HOMO) of the nucleophile and the molecular orbital (LUMO) of electrophile involved in the nucleophilic attack. MO diagrams are not necessary..arrow_forwardUsing the Frost Circle method to outline the molecular orbitals of cyclobutadiene, and identify whether it is aromatic, antiaromatic or non-aromatic. Explain.arrow_forward
- Give a molecular formula for your product if it contains no oxygens. Give the molecular formulas if your product contains one and two oxygens (some may not be possible). The molecular formula for if my molecule does not have any oxygens is C6H6, if it has one oxygen it would be C7H6O, if it was two it would be C8H7O2. Calculate the index of hydrogen deficiency, and therefore the number of rings and/or p- bonds in your unknown for each of the molecular formulas in question 3. Show yourcalculationarrow_forwardArrange the following compounds in the increasing order of reactivity towards Conc.HNO3 & Conc.H2SO4 1. Benzene 2. Chlorobenzene 3. phenol 4. Toluene 5. Nitrobenzene 5,2,1,4,3 5,1,2,4,3 5,1,4,2,3 1,2,3,4,5arrow_forwardBorazole, B3N3H6, is an unusually stable cyclic compound. Propose a structure forborazole, and explain why it is aromatic.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning