Chapter 16, Problem 16.67P

Treatment of β-D-glucose with methanol in the presence of an acid catalyst converts it into a mixture of two compounds called methyl glucosides (Section 25.3A).

In these representations, the six-membered rings are drawn as planar hexagons.

1. (a) Propose a mechanism for this conversion and account for the fact that only the ─OH on carbon 1 is transformed into an ─OCH₃ group.
2. (b) Draw the more stable chair conformation for each product.
3. (c) Which of the two products has the chair conformation of greater stability? Explain.