5. If two groups in a disubstituted cyclohexane are not the same, then the more stable conformation is the one in which the largest group is equatorial. Draw the most stable chair conformation for each of the following compounds. Use the given templates. Note that the carbon numbers are given and each template has the carbon numbers placed differently. a. cis-1-tert-butyl-4-methylcyclohexane b. trans-1-tert-butyl-4-methylcyclohexane trans-1-isopropyl-3-methylcyclohexane c.

5. If two groups in a disubstituted cyclohexane are not the same, then the more stable conformation is the one in which the largest group is equatorial. Draw the most stable chair conformation for each of the following compounds. Use the given templates. Note that the carbon numbers are given and each template has the carbon numbers placed differently. a. cis-1-tert-butyl-4-methylcyclohexane b. trans-1-tert-butyl-4-methylcyclohexane trans-1-isopropyl-3-methylcyclohexane c.

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter6: Alkanes & Alkenes

Section: Chapter Questions

Problem 1E

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Draw a stereoisomer of cis-1,2-dimethylcyclohexane. (Note that the question asks for a different stereoisomer of the named compound and not the named compound itself.) • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • In cases where there is more than one answer, just draw one. Y TAYY n[] ChemDoodle
For each of the following disubstituted cyclohexanes, indicate whether the substituents in the two chair conformers will be both equatorial in one chair conformer and both axial in the other (A) or one equatorial and one axial in each of the chair conformers (B): Drag the appropriate items to their respective bins.
Draw the most and least stable conformations of the following substituted cyclohexanes in the chair format (excluding transient conformations like half chair, twist boat and boat).
Draw the highest and lowest energy conformations. In cases where two or three conformations are degenerate, choose only one as your anwser. Use Pr, Me, H, Et in the structures.
Based on the hydrogenation reaction information, how many different alkene structures can you draw that could be Compound X? (If enantiomers are possible, count each pair of enantiomers as one structure.)
Strain of one Strain of one 1,3-diaxial interaction 1,3-diaxial interaction Strain of one 1,3-diaxial interaction H X Ph (C6H5) CO,H CN F 0.12 Me 0.9 1.5 Cl 0.7 0.1 0.25 Et 0.95 Br 0.25 i-Pr 1.1 OH 0.5 t-Bu 2.7
4. Draw the most and least stable conformations of the following substituted cyclohexanes in the chair format (excluding transient conformations like half chair, twist boat and boat). Br BL Br Br
4) Draw an alkene (minimum of 4 carbons) that is in the E conformation and a different alkene (also 4 carbon minimum) that is in the Z conformation. Provide an explanation as to what makes it E or Z.
Consider the molecule 1-bromo-2-methylbutane. C3 and C4 should be drawn as Et as in theexample. This group is called an ethyl group and can be considered a sphere about twice the sizeof a methyl group. Draw the following Newman projections sighting down the C1C2 bond... a. The lowest potential energy conformation. b. The highest potential energy staggered conformation.
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.
b. Draw a Newman projection of the given compound H viewed from C-2 to C-3 orientated according to the first template. Then use the Newman projection to demonstrate the most stable conformation around the C2-C3 bond according to the second template. (Hint: Order of decreasing group size 'Pr > CH2CH3 > CH3 > OH > Br > H] NH2 Me Ме H 'Pr Given conformation Most stable conformation
Which of these is the most stable conformation?