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Chapter 28: Question 28.55 (page 1149)

How would you convert d-glucose into each compound? More than one step is required.

(a.)

(b.)

(c.)

Short Answer

Expert verified

Answer

(a.)

(b.)

(c.)

Step by step solution

01

D-glucose

D-glucose is an isomer of glucose that is biologically active. It is the source of energy for many organisms, occurs from the plant as photosynthesis. Using certain reagents, d-glucose can be converted into a required compound.

02

Conversion of d-glucose into reactant a and b

(a) When d-glucose reacts with CH3OH,HClforms a compound which on further reaction with CH3CH2I,Ag2Ogives the following compound.

Conversion of d-glucose into a(b) When d-glucose reacts with NaBH4,CH3OH forms a compound which on further reaction with CH3I,Ag2Ogives the following compound.

Conversion of d-glucose into b

03

Conversion of d-glucose into reactant c

(c) When d-glucose reacts with Br2,H2O forms a compound which on further reaction with Ac2O, pyridine gives the following compound.

Conversion of d-glucose into c

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Most popular questions from this chapter

What two aldoses yield D-xylose on Wohl degradation?

Convert each compound to a Fischer projection and label each stereogenic center as R or S.

(a.)

(b.)

(c.)

(d.)

(e.)

(f.)

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 D-altrose is treated with each reagent.

Cellobiose, a disaccharide obtained by the hydrolysis of cellulose, is composed of two glucose units joined together in a 1鈫�4-尾- glycoside bond. What is the structure of cellobiose?
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