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Question. Cellulose is converted to cellulose acetateby treatment with acetic anhydride and pyridine. Cellulose acetate is soluble in common organic solvents, and it is easily dissolved and spun into fibres. Show the structure of cellulose acetate.

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01

Cellulose acetate

Cellulose acetate is a cellulose derivative and a biodegradable material. It is partially acetylated cellulose in which acetyl content ranges from mono to triacetate groups. Cellulose is converted to cellulose acetate by treatment with acetic anhydride and pyridine.

02

Structure of cellulose acetate

The most common form of cellulose acetate possesses acetate groups on two of every three hydroxyls of anhydroglucose unit. The anhydroglucose unit is the repeating cellulose unit with three hydroxyl groups that react and get converted to acetate esters. It is soluble in organic solvents.

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Most popular questions from this chapter

Cellulose is converted to cellulose acetateby treatment with acetic anhydride and pyridine. Cellulose acetate is soluble in common organic solvents, and it is easily dissolved and spun into fibers. Show the structure of cellulose acetate.

The relative configurations of the stereoisomers of tartaric acid were established by the following synthesis:

(1) D-(+)-glyceraldehydediastereomers A and B (separated)

(2) Hydrolysis of A and B using aqueous Ba(OH)2 gave C and D, respectively.

(3) HNO3 oxidation of C and D gave (-)-tartaric acid and meso-tartaric acid, respectively.

(a) You know the absolute configuration of D-(+)-glyceraldehyde, Use Fischer projections to show the absolute configurations of products A, B, C, and D.

(b) Show the absolute configurations of the three stereoisomers of tartaric acid: (+)-tartaric acid, (-)-tartaric acid, and meso-tartaric acid.

(a) Give the products expected when (-)-erythrose reacts with HCN.

(b) What is the relationship between the products? How might they be separated?

(c) Are the products optically active? Explain.

(a) Figure 23-2 shows that the degradation of D-glucose gives D-arabinose, an aldopentose. Arabinose is most stable in its furanose form. Draw D-arabinofuranose.

(b) Ribose, the C2 epimer of arabinose, is most stable in its furanose form. Draw D-ribofuranose.

Erwin Chargaffโ€™s discovery that DNA contains equimolar amounts of guanine and cytosine and also equimolar amounts of adenine and thymine has come to be known as Chargaffโ€™s rule:

G = C and A = T

(a) Does Chargaffโ€™s rule imply that equal amounts of guanine and adenine are present in DNA? That is, does G = A?

(b) Does Chargaffโ€™s rule imply that the sum of the purine residues equals the sum of the pyrimidine residues? That is, does A + G = C + T?

(c) Does Chargaffโ€™s rule apply only to double-stranded DNA, or would it also apply to each individual strand if the double helical strand were separated into its two complementary strands?

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