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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: mee-ow on October 02, 2016, 01:28:43 PM

Title: Benzyl group larger than phenyl group, but has a smaller diaxial interaction?
Post by: mee-ow on October 02, 2016, 01:28:43 PM

Why would a benzyl group have a smaller diaxial interaction than a phenyl group (in a monosubstituted cyclohexane)?

Title: Re: Benzyl group larger than phenyl group, but has a smaller diaxial interaction?
Post by: AWK on October 02, 2016, 01:33:55 PM

Think about labile conformation of benzyl group.

Title: Re: Benzyl group larger than phenyl group, but has a smaller diaxial interaction?
Post by: mee-ow on October 02, 2016, 01:41:27 PM

Would you mind expanding a bit please?

EDIT: So, I'm thinking that, with the benzyl-substituted cyclohexane, the CH2 is closer to the axial hydrogens, so it participates more in the 1,3-diaxial interactions than the larger C6H5. With the phenyl-substituted cyclohexane the C6H5 is what interacts with the axial hydrogens.