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Q7E from 2014 final

Posted: Sat Mar 12, 2016 10:15 pm
by 004638100
This part says to draw the newman digram for 3-chloro-4,4,4-trihydroxy-3-methylbutanenitrile. I was wondering how you know that it is a gauche and not anti.

Re: Q7E from 2014 final

Posted: Sat Mar 12, 2016 11:34 pm
by Chem_Mod
CN and C(OH)3 are the biggest substituents on the C2 and C3 carbons, respectively. So they'd be anti to each other.
The gauche comment is just saying that C(OH)3 has to be gauche to the hydrogens because then it has the least steric clash. It's the same as saying that C(OH)3 and CN are anti to each other.