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OWLv2 for Bettelheim/Brown/Campbell/Farrell/Torres' Introduction to General, Organic and Biochemistry, 11th Edition, [Instant Access], 1 term (6 months)
11th Edition
ISBN: 9781305106734
Author: Frederick A. Bettelheim; William H. Brown; Mary K. Campbell; Shawn O. Farrell; Omar Torres
Publisher: Cengage Learning US
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Chapter 13, Problem 13.12P
13-12 One analogy often used to explain the concept of a resonance hybrid is to relate a rhinoceros to a unicorn and a dragon. Explain the reasoning in this analogy and how it might relate to a resonance hybrid.
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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.
▸ View Available Hint(s)
VAΣ
ΜΕ ΑΣΦ
Np, N₁ = 82,126
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Previous Answers
?
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 13 Solutions
OWLv2 for Bettelheim/Brown/Campbell/Farrell/Torres' Introduction to General, Organic and Biochemistry, 11th Edition, [Instant Access], 1 term (6 months)
Ch. 13.2 - Prob. 13.1PCh. 13 - Answer true or false. Alkenes, alkynes, and arenes...Ch. 13 - 13-3 What is the difference in structure between a...Ch. 13 - 13-4 Define aromatic compound.Ch. 13 - 13-5 Why are alkenes, alkynes, and aromatic...Ch. 13 - 13-B Do aromatic rings have double bonds? Are they...Ch. 13 - 13-7 Can an aromatic compound be a saturated...Ch. 13 - Draw at least two structural formulas for each of...Ch. 13 - 13-9 Write a structural formula and the name for...Ch. 13 - 13-10 Account for the fact that the six-membered...
Ch. 13 - 13-11 Explain why the compound 1,4-dichlorobenzene...Ch. 13 - 13-12 One analogy often used to explain the...Ch. 13 - 13-13 Answer true or false. A phenyl group has the...Ch. 13 - Prob. 13.14PCh. 13 - 13-15 Draw structural formulas for these compounds...Ch. 13 - 13-16 We say that naphthalene, anthracene,...Ch. 13 - 13-17 Following is the structural formula of...Ch. 13 - 13-18 Answer true or false. Benzene does not...Ch. 13 - 13-19 Suppose you have unlabeled bottles of...Ch. 13 - 13-20 Three products with the molecular formula...Ch. 13 - 13-21 The reaction of bromine with toluene in the...Ch. 13 - 13-22 What reagents and/or catalysts are necessary...Ch. 13 - 13-23 What reagents and/or catalysts are necessary...Ch. 13 - Prob. 13.24PCh. 13 - 13-25 Answer true or false. (a) Phenols and...Ch. 13 - 13-26 Both phenol and cyclohexanol are only...Ch. 13 - 13-27 Define autoxidation.Ch. 13 - 13*28 Autoxidation is described as a radical-chain...Ch. 13 - 13-29 Show that if you add Steps 2a and 2b of the...Ch. 13 - 13-30 How does vitamin E function as an...Ch. 13 - 13-31 What structural features are common to...Ch. 13 - 13*32 Black-and-white photography is a commercial...Ch. 13 - 13-33 Following is the structural formula of...Ch. 13 - 13-34 (Chemical Connections 13A) From what parts...Ch. 13 - Prob. 13.35PCh. 13 - 13-36 (Chemical Connections 13A, Would you expect...Ch. 13 - Prob. 13.37PCh. 13 - 13-38 (Chemical Connections 13A) What is meant by...Ch. 13 - 13-39 (Chemical Connections 13B) What is a...Ch. 13 - 13-40 (Chemical Connections 130 In the absence of...Ch. 13 - Prob. 13.41PCh. 13 - 13-42 (Chemical Connections 13E) What are the...Ch. 13 - 13-43 (Chemical Connections 13E) Which features of...Ch. 13 - 13-44 (Chemical Connections 13E) What color would...Ch. 13 - Prob. 13.45PCh. 13 - Prob. 13.46PCh. 13 - Prob. 13.47PCh. 13 - 13-48 (Chemical Connections 13F, How many...Ch. 13 - 13-49 (Chemical Connections 13F) In what ways is...Ch. 13 - 13*50 The structure for naphthalene given in...Ch. 13 - 13-51 Draw structural formulas for these...Ch. 13 - 13-52 2,6-Di-/ezY-butyl-4-methylphenol (BHT,...Ch. 13 - 13-53 Write the structural formula for the product...Ch. 13 - 13-54 Styrene reacts with bromine to give a...Ch. 13 - 13-55 When toluene is treated with Br, in the...Ch. 13 - 13-56 Four alternatives to the structure of...Ch. 13 - 13-57 Benzene, as we have seen in this chapter, is...
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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
- 32S 16 Enter your answers numerically separated by a comma. Np. Nn = 跖 ΟΙ ΑΣΦ Submit Request Answer ? protons, neutronsarrow_forward2. Which dimethylcyclohexane compounds shown below exhibit symmetry and therefore are not chiral and would not rotate plane polarized light. 1 CH3 CH CH3 CH3 2 3 CH3arrow_forwardDon't used hand raitingarrow_forward
- Can you please explain why the answer is structures 2 and 3? Please include a detailed explanation and show how the synthesis can be done with those two structures.arrow_forwardCan you please explain why the correct answer to this question is option 2? I am having trouble understanding how and why. Please provide a detailed explanation and a drawing of how the diene and dienophile would create the product in the question.arrow_forwardCan you please explain why the correct answer is molecules 2 and 4? Base your explanation off of the rules for aromaticity and well as the principles of the Huckel rule of aromaticity. Please give a detailed explanation of what Hucekl's rule is.arrow_forward
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