This exercise is to be completed during your lab period during the week of October 24-30, 2018.
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1 MOLECULAR MODELLING EXERCISE II This exercise is to be completed during your lab period during the week of October 24-30, You will need to continue to know and understand, and be able to apply, the following terms eclipsed, skew, staggered, homologous series, dihedral angle, conformation, fully eclipsed, gauche, anti, 1,3-diaxial interaction, 1,4 interaction, flagstaff-bowsprit interaction, equatorial, and axial all in the context of conformational analysis. All this material is testable in TEST 3 and in the Final exam for the course. 1] Make a model of cyclobutane, draw this 3D molecule in 2D using a Newman projection (NP). You may need to look on the internet or in the textbook to help you with this. This molecule can be drawn using two pairs of carbon atoms in Newman style projection. Label the drawings with dihedral angles and appropriate names. Are there any other conformations that you haven t drawn? If so, what are they called? Comment on the stability of this molecule and explain.
2 2] Now make a model of cyclopentane and draw this 3D molecule in 2D using a NP. Again, you may need to look on the internet or in the textbook to help you with this. This molecule can be drawn using two pairs of carbon atoms, as in 1]. Label the drawings with dihedral angles and appropriate names. Are there any other conformations that you haven t drawn? If so, what are they called? Comment on the stability of this molecule and explain.
3 3] Now make a model of cyclohexane and draw this 3D molecule in 2D using a NP. Once more, you may need to look on the internet or in the textbook to help you with this. This molecule can be drawn using two pairs of carbon atoms in Newman style projection. Label the drawings with dihedral angles and appropriate names. Draw as many different NPs as you can and label each one. Are there any other conformations that you haven t drawn? If so, what are they called? Comment on the stability of this molecule and each of the conformations and explain.
4 4] Now make two different models of 1,2-diethylcyclohexane (one for cis and one from trans) and draw these 3D molecules in 2D using NPs. Repeat everything in 3] for these molecules.
5 5] Now make two different models of 1,3-dibromocyclohexane (one for cis and one from trans) and draw these 3D molecules in 2D using NPs. Repeat everything in 3] for these molecules.
6 6] Now make two different models of 1,4-diaminolcyclohexane (one for cis and one from trans) and draw these 3D molecules in 2D using NPs. Repeat everything in 3] for these molecules.
7 AFTER LAB EXTENSION EXERCISE for MOLECULAR MODELLING EXERCISE II. INSTRUCTIONS 1. Working in groups of up to 4 students, only pass one exercise in per group. I advise you to work in groups; these do not have to be lab group-based. 2. DO NOT DO THIS EXERCISE WHILE YOU ARE IN THE LAB. 3. You will need to think about this quite a bit and I would advise that you discuss this with other group members. 4. Photographs should have appropriate backgrounds so that it is clear what they are showing. 5. Pass in your work on a USB drive in MS Word format only. The photographs must be part of the file, not separate. A] Why is the carbon framework of cyclohexane usually drawn in a chair form? Why is the boat not common? Make a model of cyclohexane again. Take photographs of the most stable and least stable forms. Comment on these structures using appropriate language. Take a photograph that shows a 1,4-interaction and comment upon this in your Word file. B] Make a model of cyclooctane. Take photographs and comment in your Word file about these. C] Make a model of the organic molecule that is commonly called cis decalin. Take photographs and comment on these in your Word file. D] Make a model of the organic molecule that is commonly called trans decalin. Take photographs and comment on these in your Word file. E] Compare and contrast what you have seen in C] and D] F] Look up the carbon backbone structure of cholesterol. Attempt to make a model of this, take photos and comment in your Word file. Pass in this extension assignment exercise on a USB drive (memory stick), by 9am on Monday 5 November 2018 in the envelope(s) hanging on Dr. Hoyle s office door Cox 125. Early submissions are very welcome.
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