Answered: Draw (1R,3S)-1,3-dimethylcyclohexane,…

Draw (1R,3S)-1,3-dimethylcyclohexane, in its minimum energy conformation. Then draw the Newman Projection for this structure with the correct stereochemistry and in its minimum energy state.

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter6: Alkanes & Alkenes

Section: Chapter Questions

Problem 4E: Consider the molecule 1-bromo-2-methylbutane. C3 and C4 should be drawn as Et as in theexample. This...

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Concept explainers

Alkanes and Cycloalkanes

Alkanes are saturated organic compounds which are made up of C and H atoms. Alkanes have the general formula of CnH2n+2. Alkane contains sp3 hybridized carbon atoms with four sigmas (σ) bonds & every hydrogen atom is connected with one of the carbon atoms. The size of the alkane could be determined by the number of carbon atoms located in it.

Question

Draw (1R,3S)-1,3-dimethylcyclohexane, in its minimum energy conformation. Then draw the Newman Projection for this structure with the correct stereochemistry and in its minimum energy state.

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Step 1: Introduction to conformation of cyclohexane

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Step 2: Substituted cyclohexane

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Step 3: Minimum energy conformer

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Why is 3-methyl on a dashed wedge? why is it not on a solid wedge?

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Fill in the blanks: cis-1,3-Dimethylcyclohexane has two different chair conformations: one withboth methyl groups in __________ positions and one with both methyl groups in ____________ positions.
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?
[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.
- Sight along the C2-C3 bond of butan-2-amine (CH3CH(NH2)CH2CH3), and draw a Newman projection of the (a) second most stable, and the (b) second least stable conformation. - Draw the most stable chair conformation for Bornesitol.
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.
Draw 2,4-dimethylhexane as a bond-line structure. Then, looking down the C3 – C4 bond, draw a Newman projection representation of the 1) lowest energy (most stable) and 2) highest energy (least stable) conformations.
(c) Draw the Newman projection of the most stable conformation of this molecule around the bond indicated in bold (you may consider either carbon of this bond to be the front carbon). You can use the structure below as a template. (d) Now draw the Newman projection of the same compound in the gauche conformation:
Sight along the C2 - C; bond of 2,3 -dimethylbutane, and draw a Newman projections for all the staggered and eclipsed conformation. Draw the expected potential energy diagram for this molecule. 2 3 4 ĈH3-CH2 – CH – CH3 CH3 CH3 2, 3 - dimethyl butane
Using a Newman projection and your knowledge of conformational analysis, draw the two limiting conformations of TMS(Tetramethylsilane) along any C-Si bond (Lowest energy Highest energy conformation)
For 1-bromobutane draw Newman projections for the Syn-periplanar, conformation. the Anti- periplanar conformation and a Gauche conformation. Use C2 as the front carbon and C3 as the back carbon. Label each conformation, circle the highest energy conformation and underline the lowest energy conformation.
(5) Draw the most stable chair conformation of the cyclohexane shown below. CH3 CI H3C Br OH CH3
6. Draw the chair conformation and its ring-interconversion isomer of both cis and trans-1-cyclobutyl-2- methylcyclohexane and rank the four structures for stability (1 = most stable to 4 = least stable; no justifications needed). Don't forget to draw in your cyclohexane ring hydrogens!