Question
Asked Mar 4, 2020
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What glycosides are formed when each monosaccharide is treated with CH3CH2OH, HCl: (a) β-D-mannose; (b) α-D-gulose; (c) β-D-fructose?

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Expert Answer

Step 1

Hemiacetal converts into acetal when a monosaccharide is treated with alcohol and HCl. The acetal formed is known as glycoside. The formation of acetal involves generation of planner carbocation which undergoes nucleophilic attack from two different directions. Two anomers (α and β) are produced in the reaction.

Step 2

(a)The chair conformation of β-D-mannose is given below,

Chemistry homework question answer, step 2, image 1

Step 3

The glycoside formed by the treatment of β-D-mannose with CH3CH2OH and HCl is shown below,

Chemistry homework question answer, step 3, image 1

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