Cyclooctatetraene (8-annulene) is non-aromatic because all four pi bonds are not found in the sameplane in its lowest energy conformation. If this compound is reduced by two electrons to generatethe dianion, it exhibits aromatic characteristics. Draw the pi MO diagram for these compounds ifthey are planar, and fill in the electrons. Based on that picture explain the difference in theiraromaticity.

The delocalization energy is the extra stability a compound has as a result of having delocalized…

Answered: Cyclooctatetraene (8-annulene) is…

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter7: Cycloalkanes

Section: Chapter Questions

Problem 12CTQ: Fill in the blanks: cis-1,3-Dimethylcyclohexane has two different chair conformations: one withboth...

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Build a model of methylcyclohexane, and use the model to complete the following Newmanprojections of methylcyclohexane in the chair conformation: a. When the methyl group is in an axial or equatorial (circle one) position, the molecule is inits lowest potential energy conformation. b. Label one Newman projection above anti and the other gauche to describe the relationshipbetween the methyl group and C3 of the ring. c. In general, which is a lower PE conformation, anti or gauche? d. Explain how your answer to b and c provide an explanation for why it is more favorable fora large group to be in an equatorial than an axial position.
When you obtained a geometry optimized structure of methylcyclopentane, did you determine the energy of the most stable conformation? Why or why not?
Consider the structural/conformational isomers of isopropyldimethylcyclohexane shown below. Match each isomer to the statement that best describes its properties. VHas the least steric repulsion / steric strain. EVHas the most torsional and steric strain overall Me iPr, VHas a syn-pentane interaction between two (or more) non-hydrogen substituents Me VIs the lowest energy boat conformation shown В. H. Ме iPr Me C. Me iPr `Me H D. iPr Me Me E. Me Me H- iPr
[Referenca cis-2,5-dimethyl-1,3-dioxane The structure of cis-2,5-dimethyl-1,3-dioxane is shown above, without stereochemistry. In the most stable chair conformation, predict the orientation of the two methyl group both equat 1 axial and In the sketchpad, draw the structure of cis-2,5-dimethyl-1,3-dioxane. both axial • Draw your ring as a flat hexagon with wedge/dash bonds to indicate stereochemistry. If a group is achiral, do not use wedged or hashed bonds on it. • In cases where there is more than one answer, just draw one.
provide the chair conformation of methylcyclohexane with the methy group in the axial position
(B) Draw two chair conformations of the following substituted cyclohexane and identify the most stable conformation. Clearly show the axial and equatorial bonds.
Consider 1-bromopropane, CH3CH2CH2Br. (a) Draw a Newman projection for the conformation in which CH3 and -Br are anti (dihedral angle 180°). (b) Draw Newman projections for the conformations in which - CH3 and -Br are gauche (dihedral angles 60° and 300°). (c) Which of these is the lowest energy conformation? (d) Which of these conformations, if any, are related by reflection?
translate the bond-line notation structure to the Newman projection by filling int the missing groups (A, B, C, D or E) on the lines in the Newman projection so they match the conformation given in the original structure. Circle if the conformation is a staggered or eclipsed.
Which chair structure accurately represents the lowest energy conformation of the compound shown in its bond-line structure below? da
(5) Draw the most stable chair conformation of the cyclohexane shown below. CH3 CI H3C Br OH CH3
In each case below, identify the higest and lowest energy conformations. In cases where two or three conformations are degenerate, choose only one as your anwser. Use Me, H, and Et when drawing the structures.
What structure has the lowest energy?

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