1,2-bis(methylthio)cyclohexane has two asymmetric carbons, thus 4 possible stereoisomers. However, one stereoisomer is a meso compound, so there are only 3. a) Draw all possible stereoisomers. Change the given structures by adding dashes and wedges. Draw the correct stereoisomer of each configuration above the provided labels. i.e draw the (R, S) configuration above the label (R, S). b) Label the enantiomers, diastereomers, and meso compound by filling in the chart (If you redraw the molecules, keep in the same order with the amine groups on the right side of the molecule!) Change the squiggly lines to dashed or wedges in the given structures to make 3 stereoisomers NH₂ &.x¢¢ NH₂ NH₂ NH₂ cyclopentane-1,2-diamine Enantiomers are structures Diastereomers are structures The meso compound is structure 1 (R, S) NH₂ Structure(s) "NH₂ 2 (S, S) NH ₂ "NH 2 3 (R, R)

1,2-bis(methylthio)cyclohexane has two asymmetric carbons, thus 4 possible stereoisomers. However, one stereoisomer is a meso compound, so there are only 3. a) Draw all possible stereoisomers. Change the given structures by adding dashes and wedges. Draw the correct stereoisomer of each configuration above the provided labels. i.e draw the (R, S) configuration above the label (R, S). b) Label the enantiomers, diastereomers, and meso compound by filling in the chart (If you redraw the molecules, keep in the same order with the amine groups on the right side of the molecule!) Change the squiggly lines to dashed or wedges in the given structures to make 3 stereoisomers NH₂ &.x¢¢ NH₂ NH₂ NH₂ cyclopentane-1,2-diamine Enantiomers are structures Diastereomers are structures The meso compound is structure 1 (R, S) NH₂ Structure(s) "NH₂ 2 (S, S) NH ₂ "NH 2 3 (R, R)

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter6: Alkanes & Alkenes

Section: Chapter Questions

Problem 21E

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Draw all stereoisomers and indicate which ones if any, are meso compounds...
For the the structure shown below, Part A) Draw the Newman projections and 3-D sawhorse structures corresponding to the lowest and highest energy conformations for rotation around the C2-C3 bond. Draw the Newman projections looking FROM THE C2 CARBON TO THE C3 CARBON (i.e. with the C2 carbon in the "front"). Part B) Determine the energy difference between the lowest and highest conformations, and be sure to clearly show each energy contribution that you are including in your calculation. 2,3-dimethylpentane ECLIPSING Interactions AB Energy kcal/mol H/H 1.0 H / Me 1.4 H/Et 1.5 H/i-Pr 1.6 H/t-Bu 3.0 Me / Me 2.6 Me / Et 2.7 Me/i-Pr 3.0 GAUCHE A. Interactions Me / Me Me / Et Me / i-Pr Me / t-Bu Et / Et Et / -Pr Et/t-Bu i-Pr/i-Pr B Energy kcal/mol 0.9 0.95 1.1 2.7 1.1 1.6 3.0 2.0
For the the structure shown below, Part A) Draw the Newman projections and 3-D sawhorse structures corresponding to the lowest and highest energy conformations for rotation around the C2-C3 bond. Draw the Newman projections looking FROM THE C2 CARBON TO THE C3 CARBON (i.e. with the C2 carbon in the "front"). Part B) Determine the energy difference between the lowest and highest conformations, and be sure to clearly show each energy contribution that you are including in your calculation. Lowest Energy Conformation 3-D sawhorse Newman ECLIPSING Interactions AB H/H H/Me H / Et H/i-Pr Energy kcal/mol 1.0 1.4 1.5 1.6 H/ t-Bu 3.0 Me / Me 2.6 Me / Et 2.7 Mei-Pr 3.0 GAUCHE A. Interactions Me / Me Me / Et Me / i-Pr Me / t-Bu Et / Et Et/i-Pr Et / t-Bu i-Pr/i-Pr 3-D sawhorse Energy kcal/mol Newman 0.9 0.95 1.1 2.7 1.1 1.6 Highest Energy Conformation 3.0 2.0
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4. For the structure shown below, Part A) Draw the Newman projections and 3-D sawhorse structures corresponding to the lowest and highest energy conformations for rotation around the C2-C3 bond. Draw the Newman projections looking FROM THE C2 CARBON TO THE C3 CARBON (i.e. with the C2 carbon in the "front"). Part B) Determine the energy difference between the lowest and highest conformations, and be sure to clearly show each energy contribution that you are including in your calculation. Lowest Energy Conformation 3-D sawhorse Newman ECLIPSING Interactions Energy Difference: AB Energy kcal/mol H/H 1.0 H/Me 1.4 H/Et 1.5 H/Pr 1.6 H/1-Bu 3.0 Me / Me 2.6 Me/Et 2.7 Me/i-Pr 3.0 GAUCHE A Interactions Energy kcal/mol Me / Me 0.9 Me / Et 0.95 Me/i-Pr 1.1 Me/t-Bu 2.7 Et/Et 1.1 Et/i-Pr 1.6 Et/t-Bu 3.0 i-Pr/i-Pr 2.0 Highest Energy Conformation 3-D sawhorse Newman 1
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