Be sure to answer all parts. Menthol, used to flavor various foods and tobacco, is the most stable stereoisomer of 2-isopropyl-5-methylcyclohexanol. Draw its most stable structure in the chair conformation. draw structure... Is the hydroxyl group cis or trans to the isopropyl group? The hydroxyl group is [(select) to the isopropyl group. Is the hydroxyl group cis or trans to the methyl group? The hydroxyl is (select) to the methyl group.

Be sure to answer all parts. Menthol, used to flavor various foods and tobacco, is the most stable stereoisomer of 2-isopropyl-5-methylcyclohexanol. Draw its most stable structure in the chair conformation. draw structure... Is the hydroxyl group cis or trans to the isopropyl group? The hydroxyl group is [(select) to the isopropyl group. Is the hydroxyl group cis or trans to the methyl group? The hydroxyl is (select) to the methyl group.

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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Following is a chair conformation of cyclohexane with the carbon atoms numbered 1 through 6. (a) Draw hydrogen atoms that are above the plane of the ring on carbons 1 and 2 and below the plane of the ring on carbon 4. (b) Which of these hydrogens are equatorial? Which are axial? (c) Draw the alternative chair conformation. Which hydrogens are equatorial? Which are axial? Which are above the plane of the ring? Which are below it?
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.
- 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.
2. For the following structure: (1S, 2R, 4R)-2-chloro-1-isopropyl-4-methylcyclohexane a. draw both chair conformations for the molecule b. identify whether the more stable stereoisomer.
4. Draw the chair conformations of cis-1,2-dimethylcyclohexane. Label each and rank their stability (lower energy = more stability) from most stable to least. Provide a rationale in terms of atom-atom interactions.
6. Newman projections to Lewis structures From the following Newman projections, draw the corresponding Lewis structure in the same conformation. A) B) H. H CH3 H₂C N H OH CI Br CH3 H 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!
How many energetically different eclipsed conformations does 1-bromo-2-methylpropane, viewed along the C1- C2 bond, have? To be able to answer the question, draw and analyze the Newman projections for the different conformations.
2. H3CO H3CO HO 1. Consider the molecule shown below. [1] Draw the two chair conformations for the compound. [2] Identify which of the two chair conformations is more stable and explain why. H3CO Jonoto NH₂ How are the following molecules related? (exactly the same, completely different, constitutional isomers, enantiomers, or diastereomers). OH OH OCH3 HO“ OH H3CO H3CO is content is protected and may not be shared, uploaded of ributed OCH3 HO,,, OH O... "OCH3
3. For the following conformation of 1,3-dimethylcyclohexane: H₂C. -CH3 A a) Is this a chair conformation of cis- or trans- isomer of 1,3-dimethylcyclohexane? b) Draw the alternative chair conformation of this compound. Which chair conformation is more stable? c) Draw a planar hexagon representation of the isomer A. d) Draw a Newman projection of isomer A.
[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.
4. Predict the most stable conformation of cis-1- isopropyl-4-ethylcyclohexane. A) The isopropyl group is axial and the ethyl group is equatorial. B) Both groups are axial. C) Both groups are equatorial. D) The isopropyl group is equatorial and the ethyl group is axial. E) There is no way to predict for this molecule.