6. Predict which of the following two isomers (cis- or trans-) will undergo an E2 elimination...
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(a) (b) .CI For each compound below 1. Draw representations for the cis and trans isomers using a hexagon for the six- (i) membered ring, and wedges and dashes for substituents. Draw the two possible chair conformations for the cis isomer. Which conformation, if (ii) either, is more stable? Draw the two possible chair conformations for the trans isomer. Which conformation. (iii) if either, is more stable? Which isomer, cis or trans, is...
11. Build the chair and boat conformations and identify the most stable conformation. Identify the 1,3-diaxial interactions. 12. Draw the most stable conformation of (a) ethylcyclohexane (b) 3-isopropyl-1,1-dimethylcyclohexane (c) cis-1-tert-butyl-4-isopropylcyclohexane 13. Draw all possible conformations of 1,4-dimethylcyclohexane and identify the most stable conformation 14. (a) Draw both chair conformations of cis-1,2-dimethylcyclohexane, and determine which conformer is more stable. (b) Repeat for the trans isomer. (c) Predict which isomer (cis or trans) is more stable. 15. (a) Draw both chair conformations...
11/8/19 The cis- and trans-isomers of 1-bromo-2-methylcyclohexane are shown below. One of these isomers undergoes E2 elimination 50 time faster than the other. Illustrate the E2 mechanism using the chair conformers to explain why one isomer is much faster and give the major product of each reaction. 1-BUOK 1-BOK Illustrate the Sw2 mechanism for the reaction below and show what has happened to the stereochemistry of the compound. NaCN acetone
7. (13 points) For the compound 1-tert-butyl-4-methylcyclohexane: a. Draw the two possible chair conformations for the cis isomer, Which conformation, if either, is more stable? Circle one b. Draw the two possible chair conformations for the cis isomer, Which conformation, if either, is more stable? Circle one trans: C. Between the two more stable isomers circled above, which is more stable? Why?
15. Draw all possible elimination products (including cis/trans isomers). Decide which will be the major elimination product and briefly explain why. NaOC(CH3)3 a. Ci KOCH NaOH Кос(CH3 NaOCH,CH3 stions decide which will be a faster E2 reaction. Explain.
6. Build the cyclobutane ring and study the angle strain and torsional strain. Draw the structures to explain these factors. 7. The conformation of cyclobutane is slightly folded. Folding gives partial relief from the eclipsing of bonds, as shown in the Newman projection. Compare this actual structure with the hypothetical planar structure. Draw the relevant structures. 8. trans-1,2-Dimethylcyclobutane is more stable than cis-1,2-dimethylcyclobutane, but cis-1,3- dimethylcyclobutane is more stable than trans-1,3-dimethylcyclobutane. Use the molecular models to find the reasons for...
1. Now construct cis-1,2-dimethylcyclohexane in the chair conformation and draw it. Perform the ring flip and draw that conformation. Which of the two conformations is preferred? This compound is meso, find the conformation that accounts for this? 2. Construct and draw trans-1-ethyl-2-methylcyclohexane in the chair conformation. Perform the ring flip and draw that conformation. Which conformation is preferred/most stable? Why? Construct and draw the cis isomer in the most stable chair conformation. Perform the ring flip and draw that conformation....
9. Draw two different chair conformations of cyclohexanol, showing all hydropen atoms. Identify each position as axial or equatorial 10. Draw the most stable chair conformation of the following molecules, and estimate the amount of strain in each: (a) trans-1-Chloro-3-methylcyclohexane (b) cis-1-Ethyl-2-methylcyclohexane (c) cis-1-Bromo-4-ethylcyclohexane (d) cis-1-tert-Butylcyclohexane 11. Which isomer is more stable, cis-decalin or trans-decalin? Explain. 12. Glucose exists in two forms having a 36:64 ratio at equilibrium. Draw a skeletal structure of each, describe the difference between them and...
Prelab Assignment Prior to the laboratory, complete the following Pre-lab Question(s): 1. Cis and Trans isomers of 1,2-dichlorocyclohexane, 1,3-dichlorocyclohexane and 1,4- dichlorocyclohexane - Draw the perspective, Chair and mirror image (if applicable) of each isomer. Perspective (Wedge dash) Chair conformation Drawing Mirror Image chair Chiral? Cis-1,2-dichlorowyclohexane Trans-1.2-dichlorocyclone Is either isomer a mese compound? If yes, draw the plane of symmetry on the mese compound What is the errochemical relationship between these is transiomer? C-1,3-dichlorocyclohexane Trans-1,3-dichloroceae Is either somer amese compound?...
3. Explain why molecule A readily undergoes E2 elimination whole molecule B does not undergo E2 elimination: (trans-decalin for both) (Draw the chair forms of A and B and show whether an anti- or synperiplanar conformation is possible. Models are VERY useful here.)