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Chapter 28: Question 28.34 (page 1141)

Draw a stepwise mechanism for the conversion of β-D-glucose to both anomers of N-ethyl glucopyranoside, the equation written in Reaction [1].

Short Answer

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Answer

Mechanism

Step by step solution

01

β-D-glucose

In theβ-D-glucose, the configuration at C-1 and C-5 carbons are trans to each other. This compound reacts with an amine under mildly acidic conditions forms a carbocation intermediate.

02

Carbocation

The hydroxyl group reacts with the proton and formsH2O+ ; after losing thisH2O+ during the reaction, a carbocation intermediate is formed.

The shape of the carbocation is planar, and the nucleophile can attack it both above and below the plane and forms alpha and beta-N-ethyl glycopyranoside.

03

Mechanism

The mechanism involves the formation of a carbocation in step 1 and the attack of the nucleophile on the carbocation in step 2.

Stepwise mechanism

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Most popular questions from this chapter

Draw a Haworth projection for each compound using the structures in Figures 28.4 and 28.5.

Draw a Fischer projection of the monosaccharide from which each of the following glycosides was prepared.

What aldoses are formed when the following aldoses are subjected to the Kiliani-Fischer synthesis: (a) D-threose; (b) D-ribose; (c) D-galactose

Consider the tetrasaccharide stachyose drawn below. Stachyose is found in white jasmine, soybeans, and lentils. Because humans cannot digest it, its consumption causes flatulence.

a. Label all glycoside bonds.

c. What products are formed when stachyose is hydrolyzed with H3O+?

d. Is stachyose a reducing sugar?

e. What product is formed when stachyose is treated with excess CH3I, Ag2O?

f. What products are formed when the product in (e) is treated with H3O+?

Draw the products formed when α-D-glucoseis treated with each reagent.

a.CH3I,Ag2O

b.CH3OH,HCl

c. Ac2O, pyridine

d. The product in (a), thenH3O+

e. The product in (b), then Ac2O, pyridine

f. The product in (d), then C6H5CH2Cl,Ag2O
See all solutions

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