ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
12th Edition
ISBN: 9781119304241
Author: Solomons
Publisher: WILEY C
expand_more
expand_more
format_list_bulleted
Question
Chapter 4, Problem 45P
Interpretation Introduction
Interpretation:
The reason for non-planarity of cyclobutane ring is to be explained.
Concept introduction:
The separation of two opposite electrical charges is measured through dipole moment.
Chair conformations are the most stable conformation which accurately shows the spatial arrangement of atoms.
Equatorial bonds are parallel to the average plane of the ring while axial bonds are perpendicular to the average plane of the ring.
The conformation having bonds at the equatorial position are more stable than those having them at an axial position.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Don't used hand raiting
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
Submit
Previous Answers
?
protons, neutrons
Chapter 4 Solutions
ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
Ch. 4 - Prob. 1PPCh. 4 - Which structure does not represent...Ch. 4 - Prob. 3PPCh. 4 - Draw bond-line formulas for all of the isomers of...Ch. 4 - Prob. 5PPCh. 4 - Draw bond-line formulas and give IUPAC...Ch. 4 - Draw bond-line formulas and give IUPAC...Ch. 4 - Practice Problem 4.8 Give names for the following...Ch. 4 - Prob. 9PPCh. 4 - Prob. 10PP
Ch. 4 - Prob. 11PPCh. 4 - Give the structures and IUPAC names for all the...Ch. 4 - Prob. 13PPCh. 4 - Practice Problem 4.14 Show by a calculation (using...Ch. 4 - Practice Problem 4.15 Write structures for the cis...Ch. 4 - Practice Problem 4.16
(a) Write structural...Ch. 4 - Practice Problem 4.17 Write a conformational...Ch. 4 - Practice Problem 4.18
(a) Write the two...Ch. 4 - Prob. 19PPCh. 4 - Practice Problem 4.20 (a) What is the index of...Ch. 4 - Practice Problem 4.21
Zingiberene, a fragrant...Ch. 4 - Practice Problem 4.22 Carbonyl groups also count...Ch. 4 - Prob. 23PCh. 4 - Give systematic IUPAC names for each of the...Ch. 4 - Prob. 25PCh. 4 - Write the structure and give the IUPAC systema.tic...Ch. 4 - 4.27. Write the structure(s) of the simplest...Ch. 4 - Prob. 28PCh. 4 - 4.29. Write structures for the following...Ch. 4 - Prob. 30PCh. 4 - A spiro ring junction is one where two rings that...Ch. 4 - 4.32. Tell what is meant by a homologous series...Ch. 4 - Four different cycloalkenes will all yield...Ch. 4 - 4.34. (a) Three different alkenes yield...Ch. 4 - Prob. 35PCh. 4 - Prob. 36PCh. 4 - 4.37. Write the structures of two chair...Ch. 4 - Prob. 38PCh. 4 - Without referring to tables, decide which member...Ch. 4 - Prob. 40PCh. 4 - 4.41. Which compound would you expect to be the...Ch. 4 - Prob. 42PCh. 4 - 4.43. Write the two chair conformations of each of...Ch. 4 - Provide an explanation for the surprising fact...Ch. 4 - Prob. 45PCh. 4 - 4.46. Specify the missing compounds and/or...Ch. 4 - Consider the cis and trans isomers of...Ch. 4 - Prob. 48PCh. 4 - Open the energy-minimized 3D Molecular Models on...Ch. 4 - 4.50. Open the 3D Molecular Models on the book’s...Ch. 4 - 4.51. Open the 3D Molecular Model on the book’s...Ch. 4 - 1. The predominant conformation for D-glucose is...Ch. 4 - Prob. 2LGPCh. 4 - When 1,2-dimethylcyclohexene is allowed to react...Ch. 4 - Prob. 4LGP
Knowledge Booster
Similar questions
- 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 -CH3arrow_forward5. 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_forward
- The 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_forward32S 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_forward
- Can you please explain why the correct answer for this question is letter B? I chose letter A because I thought that a kinetic product was a 1,2-addition. Please give a detailed explanation.arrow_forwardCan 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_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning