Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 15.SE, Problem 35AP
Calicene, like azulene (Problem 15-17), has an unusually large dipole moment for a hydrocarbon. Explain, using resonance structures.
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It is not unexpected that the methoxyl substituent on a cyclohexane ring
prefers to adopt the equatorial conformation.
OMe
H
A G₂ = +0.6 kcal/mol
OMe
What is unexpected is that the closely related 2-methoxytetrahydropyran
prefers the axial conformation:
H
H
OMe
OMe
A Gp=-0.6 kcal/mol
Methoxy: CH3O group
Please be specific and clearly write the reason why this is observed. This effect that provides
stabilization of the axial OCH 3 group in this molecule is called the anomeric effect. [Recall in the way of
example, the staggered conformer of ethane is more stable than eclipsed owing to bonding MO
interacting with anti-bonding MO...]
206 Pb
82
Express your answers as integers. Enter your answers separated by a comma.
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VAΣ
ΜΕ ΑΣΦ
Np, N₁ = 82,126
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?
protons, neutrons
Please draw the inverted chair forms of the products for the two equilibrium reactions
shown below. Circle the equilibrium reaction that would have a AG = 0, i.e., the relative energy of
the reactant (to the left of the equilibrium arrows) equals the relative energy of the product? [No
requirement to show or do calculations.]
CH3
CH3
HH
CH3
1
-CH3
Chapter 15 Solutions
Organic Chemistry
Ch. 15.1 - Prob. 1PCh. 15.1 - Give IUPAC names for the following compounds:Ch. 15.1 - Prob. 3PCh. 15.2 - Pyridine is a flat, hexagonal molecule with bond...Ch. 15.3 - Prob. 5PCh. 15.4 - Draw the five resonance structures of the...Ch. 15.4 - Prob. 7PCh. 15.4 - Prob. 8PCh. 15.5 - Prob. 9PCh. 15.5 - Prob. 10P
Ch. 15.6 - Prob. 11PCh. 15.6 - How many electrons does each of the four nitrogen...Ch. 15.SE - Give IUPAC names for the following substances (red...Ch. 15.SE - All-cis cyclodecapentaene is a stable molecule...Ch. 15.SE - 1, 6-Methanonaphthalene has an interesting 1H NMR...Ch. 15.SE - Prob. 16VCCh. 15.SE - Azulene, an isomer of naphthalene, has a...Ch. 15.SE - Give IUPAC names for the following compounds:Ch. 15.SE - Draw structures corresponding to the following...Ch. 15.SE - Prob. 20APCh. 15.SE - Prob. 21APCh. 15.SE - Draw and name all possible aromatic compounds with...Ch. 15.SE - Propose structures for aromatic hydrocarbons that...Ch. 15.SE - Look at the three resonance structures of...Ch. 15.SE - Prob. 25APCh. 15.SE - Prob. 26APCh. 15.SE - Look at the five resonance structures for...Ch. 15.SE - Prob. 28APCh. 15.SE - 3-Chlorocyclopropene, on treatment with AgBF4,...Ch. 15.SE - Prob. 30APCh. 15.SE - Prob. 31APCh. 15.SE - Prob. 32APCh. 15.SE - Which would you expect to be most stable,...Ch. 15.SE - How might you convert 1, 3, 5, 7-cyclononatetraene...Ch. 15.SE - Calicene, like azulene (Problem 15-17), has an...Ch. 15.SE - Pentalene is a most elusive molecule that has been...Ch. 15.SE - Prob. 37APCh. 15.SE - Prob. 38APCh. 15.SE - Compound A, C8H10, yields three substitution...Ch. 15.SE - Prob. 40APCh. 15.SE - Propose structures for compounds that fit the...Ch. 15.SE - Prob. 42APCh. 15.SE - Prob. 43APCh. 15.SE - N-Phenylsydnone, so-named because it was first...Ch. 15.SE - Prob. 45APCh. 15.SE - Prob. 46APCh. 15.SE - Prob. 47APCh. 15.SE - Propose a structure for a molecule C14H12 that has...Ch. 15.SE - The proton NMR spectrum for a compound with...Ch. 15.SE - The proton NMR spectrum of a compound with formula...Ch. 15.SE - Aromatic substitution reactions occur by addition...Ch. 15.SE - Prob. 52APCh. 15.SE - Consider the aromatic anions below and their...Ch. 15.SE - After the reaction below, the chemical shift of Ha...Ch. 15.SE - Prob. 55APCh. 15.SE - Azo dyes are the major source of artificial color...
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- 5. Please consider the Newman projection of tartaric acid drawn below as an eclipsed conformer (1). Please draw the most stable conformer and two intermediate energy conformers noting that staggered conformers are lower in energy than eclipsed forms even if the staggered conformers have gauche relationships between groups. [Draw the substituents H and OH on the front carbons and H, OH and CO₂H on the back carbons based on staggered forms. -CO₂H is larger than -OH.] OH COH ICOOH COOH COOH 1 2 COOH COOH 3 4 Staggered Staggered Staggered (most stable) Indicate the number of each conformer above (1, 2, 3 and 4) that corresponds to the relative energies below. Ref=0 Rotation 6. (60 points) a. Are compounds 1 and 2 below enantiomers, diastereomers or identical? OH OH HO HO LOH HO HO OH 2 OH OH b. Please complete the zig-zag conformation of the compound (3R,4S)-3,4-dichloro-2,5-dimethylhexane by writing the respective atoms in the boxes. 3.arrow_forwardThe plutonium isotope with 144 neutrons Enter the chemical symbol of the isotope.arrow_forwardThe mass ratio of sodium to fluorine in sodium fluoride is 1.21:1. A sample of sodium fluoride produced 26.1 gg of sodium upon decomposition. How much fluorine was formed?arrow_forward
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