Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 22, Problem 39P

Arbutin, a compound that can be isolated from the leaves of barberry, cranberry, and pear trees, has the molecular formula C 12 H 16 O 7 . When arbutin is treated with aqueous acid or with a β -glucosidase, the reaction produces D-glucose and a compound X with the molecular formula C 6 H 6 O 2 . The 1 H NMR spectrum of compound X consists of two singlets, one at δ 6.8 ( 4 H ) and one at δ 7.9 ( 2 H ) . Methylation of arbutin followed by acidic hydrolysis yields 2,3,4,6-tetra-O-methyl-D-glucose and a compound Y ( C 7 H 8 O 2 ) . Compound Y is soluble in dilute aqueous NaOH but is insoluble in aqueous N a H C O 3 . The 1 H NMR spectrum of Y shows a singlet at δ 3.9 ( 3 H ) , a singlet at δ 4.8 ( 1 H ) , and a multiplet (that resembles a singlet) at δ 6.8 ( 4 H ) . Treating compound Y with aqueous NaOH and ( C H 3 ) 2 S O 4 produces compound Z ( C 8 H 10 O 2 ) . The 1 H NMR spectrum of Z consists of two singlets, one at δ 3.75 ( 6 H ) and one at δ 6.8 ( 4 H ) . Propose structures for arbutin and for compounds X, Y, and Z.

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NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY