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Topic: Gauche positions in cyclohexane and other alkanes  (Read 12050 times)

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Offline th3tallguy

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Gauche positions in cyclohexane and other alkanes
« on: September 27, 2012, 11:59:20 PM »
I am working on problems at the end of the chapter of my chemistry textbook and I am having trouble identifying which positions on a structure like cyclohexane are gauche. for example in a chair conformation cyclohexane which hydrogens are gauche to the equatorial hydrogen on the first carbon? neither my professor or my book has done much explaining of gauche and anti- past propane and translating those concepts to cycloalkanes has been difficult

from what I've gathered from the book Two groups are gauche when they are located on adjacent carbons and when the angle between their bonds (to the adjacent carbons) is 60°. based on this my best guess is that both the equatorial and axial hydrogens on both adjacent carbons are in the gauche position, but I could be completely wrong.

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Offline PhDoc

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Re: Gauche positions in cyclohexane and other alkanes
« Reply #2 on: September 29, 2012, 10:59:04 PM »
Take a look at the Newman projection image from the following article,

The E2 Reaction
http://lennoxtutoring.com/2011/10/03/the-e2-reaction/

Replace the methyl and bromine with hydrogens on the Newman projection.

Keep in mind the reason why you're learning about Newman projections. It's the beginning of conformational analysis in Organic Chemistry, and the example problem discussed in the article is reflective of what you will see on an exam. Depending upon your professor, the exam question could be tougher than the example I provided.

Good luck!
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