Organic Chem question

CarlKillerMiller

Diamond Member
Jul 14, 2003
3,099
0
0
I hate using ATOT for this, but I'm really pretty out of resources.

The task at hand is to draw a potential energy diagram for all of the conformations of 2-methylbutane. Normally, without that methyl subsitutent, this wouldn't be a big deal, but that's sorta screwed it for me. So, my question is this:

Is the conformation in which the methyl group and carbon 1 eclipse the hydrogens on carbon three lower or higher in energy than the conformation in which carbon 1 is anti to carbon 4 and the methyl group is staggered between carbon 4 and one of carbon 3's hydrogen?

On the one hand, the first option provides more steric interactions between carbon 3's hydrogens and carbon 1 and the methyl group. Yet, in this conformation, Carbon 1 and the methyl group are furthest from carbon 4.

On the other hand, the other configuration provides a staggered structure (+stability, lower energy) and an anti structure (more +stability, lower energy).

I'm stumped. Thanks in advance, you wonderful people!
 

James3shin

Diamond Member
Apr 5, 2004
4,426
0
76
Count the number of Anti and Gauche, whichever has the higher number of Anti, and least number of Gauche interactions is lower in energy, therefore more stable. Have fun drawing all those Neuman projections.