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Topic: Drawing boat conformation of bicyclic compound  (Read 2718 times)

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Offline FireWalkWithMe

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Drawing boat conformation of bicyclic compound
« on: June 20, 2017, 01:55:31 PM »
One of the questions in an exam the previous generation had in Organic Chemistry I was:
"Draw the conformation formula (what) of 6-methyl-8-hidroxymethyl-bicyclo[3.2.1]octane."
Searched many Organic Chemistry undergrad books and googled but couldn't find a way to do this. Did he mean to draw a bond-line structure with 3D accuracy, like the usual way of drawing bicyclic compounds? He isn't a very good professor, incredibly lazy.
Can someone solve this and post a pic of it?

Offline Babcock_Hall

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Re: Drawing boat conformation of bicyclic compound
« Reply #1 on: June 20, 2017, 04:21:36 PM »
It is a forum rule (red link near top of page) that you must show your attempt before we can help you.

Offline FireWalkWithMe

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Re: Drawing boat conformation of bicyclic compound
« Reply #2 on: June 20, 2017, 05:16:24 PM »
I'm thinking this, maybe? But I'm totally unsure, especially since it seems too easy of an answer (though I guess that would be neutralized by the confusing way the question was worded)

Offline FireWalkWithMe

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Re: Drawing boat conformation of bicyclic compound
« Reply #3 on: June 21, 2017, 07:25:55 AM »
I just noticed I picked the wrong parent, but is the rest of it correct?

Offline Babcock_Hall

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Re: Drawing boat conformation of bicyclic compound
« Reply #4 on: June 21, 2017, 09:57:30 AM »
I am a little outside of my comfort zone, but I don't see why you think it is the wrong parent.  One thing I did notice is that I would have used -CH2OH for a hydroxymethyl group.

Offline FireWalkWithMe

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Re: Drawing boat conformation of bicyclic compound
« Reply #5 on: June 21, 2017, 02:27:39 PM »
I am a little outside of my comfort zone, but I don't see why you think it is the wrong parent.  One thing I did notice is that I would have used -CH2OH for a hydroxymethyl group.

You're right about the hydroxymethyl, I was hurrying and since it wasn't important to what I was really asking wrote it mistakenly, meant to put MeO there. I think I picked the wrong parent because the longest path must be picked according to what I'm reading in Klein, and the CH3 substituent be put one carbon atom below, although I'm now confused because idk why we can't just put the CH3 where I did and go the other path, but as long as this is regarded a boat conformation it's no problem.

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