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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

What glycosides are formed when each monosaccharide is treated with CH3CH2OH, HCl:

(a) β-D-Mannose; (b)α-D-glucose ; (c) β-D-fructose ?

For D-arabinose:

  1. Draw its enantiomer.
  2. Draw an epimer at C3.
  3. Draw a diastereomer that is not an epimer.
  4. Draw a constitutional isomer that still contains a carbonyl group.

(a) Why can’t two purine bases (A and G) form a base pair and hydrogen bond to each other on two strands of DNA in the double helix? (b) Why is hydrogen bonding between guanine and cytosine more favorable than hydrogen bonding between guanine and thymine?

Treating chitin with H2O,-OH hydrolyzes its amide linkages, forming a compound called chitosan. What is the structure of chitosan? Chitosan has been used in shampoos, fibers for sutures, and wound dressings.

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+?
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