It is not unexpected that the methoxyl substituent on a cyclohexane ringprefers to adopt the equatorial conformation.OMeHA G₂ = +0.6 kcal/molOMeWhat is unexpected is that the closely related 2-methoxytetrahydropyranprefers the axial conformation:HHOMeOMeA Gp=-0.6 kcal/molMethoxy: CH3O groupPlease be specific and clearly write the reason why this is observed. This effect that providesstabilization of the axial OCH 3 group in this molecule is called the anomeric effect. [Recall in the way ofexample, the staggered conformer of ethane is more stable than eclipsed owing to bonding MOinteracting with anti-bonding MO...]

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Answered: It is not unexpected that the methoxyl…

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter2: Alkanes And Cycloalkanes

Section: Chapter Questions

Problem 2.46P

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Page of 11 ZOOM + A1. What is the arrangement of the bonds surrounding carbon in a saturated hydrocarbon? linear trigonal planar tetrahedral В trigonal bipyramidal A2. What is the definition of a constitutional isomer? A molecules with the same numbers and kinds of atoms arranged in different ways molecules with the same arrangements of atoms, but different arrangements of electrons molecules with the same connectivities, but different 3-D angles molecules with different isotopes of the same atoms В АЗ. How many hydrogen atoms does the following molecule contain? 12 В 16 18 Which functional group gives rise to a broad IR absorption between 3200 cm-1 and 3600 cm-1? A4. A O-H stretch C-H stretch O-H bend C-O stretch А5. How many resonances will appear in the 13C NMR spectrum of cyclopentanone? 3 4 Section A continues on the next page N468 ABCD ABCD ABCD
CH3 to Br- -H + Nal • product; Sy2 product of the reaction is : Аcetone H- -CH3 CH2 – CH3 CH3 CH3 CH3 CH3 it it -H H- -CH3 (d) -CH3 -H- (а) H• (Ъ) H- -CH3 -CH3 (с) H- CH -H- ČH2 – CH3 ČH2 – CH3 CH2 – CH3 CH2- CH3 2.
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compound CH3 CH₂0 CH3 — OH C- CH3 1 CH3-N - CH3 CH₂ ||| -C-H 01C- | NH₂ CH3 family ester
11. s) Draw the most stable conformation of 1,3-dichloro-2,4-difluorocyclohexane: 12. Which of the following represents the most stable conformation of 1,2,4,5- tetramethyleyclohexane? (one correct answer) CH b) CH HC H- H- CH HC CH, CH 6. Give IUPAC name for the following molecule. Include "cis" and "trans" designations if applicable. H2C-CH3 H -CH2 H- H Br
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Which of the following two conformations of cis-1-bromo-4-methylcyclohexane is more stable? Use the strain energy increments in the table below estimate the energy difference (a positive number) between them.
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Give the proper IUPAC name for the following compounds: CH,- CH, CH,- CH - CH -CH, CH, Br CH CH, Br H:-CH; CH - CH-CH, H;C CH, CH, CH, CH- CH- CH, c=C H,C-CH, CH, CH- CH, H H ОН CI
Dehydrohalogenation of 1-chloro-1-methylcyclopropane affords two alkenes (A and B) as products. Explain why A is the major product despite the fact that it contains the less substituted double bond.
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Cyclohexane derivatives exist primarily in the most stable of the available chair conformations. Give the position, axial or equatorial, of each of the three groups shown when the ring is in the most stable chair conformation. If a group divides its time equally between axial and equatorial positions, indicate this with ax/eq.

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