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Chapter 23: Q42P. (page 1240)

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

Is gentiobiose a reducing sugar? Does it mutarotate? Explain your reasoning.

. (a) An aliphatic aminoglycoside is relatively stable to base, but it is quickly hydrolyzed by dilute acid. Propose a mechanism for the acid-catalyzed hydrolysis.

(b) Ribonucleosides are not so easily hydrolyzed, requiring relatively strong acid. Using your mechanism for part (a), show why cytidine and adenosine (for example) are not so readily hydrolyzed. Explain why this stability is important for living organisms.

Draw and name the enantiomers of the sugars shown in Figure 23-2. Give the relative configuration (D or L) and the sign of the rotation in each case.

Emil Fischer synthesized L-gulose, an unusual aldohexose that reduces to give D-glucitol. Suggest a structure for this L sugar, and show how L-gulose gives the same alditol as D-glucose. (Hint: D-Glucitol has -CH2OHgroups at both ends. Either of these primary alcohol groups might have come from reduction of an aldehyde.)

An important protecting group developed specifically for polyhydroxy compounds like nucleosides is the tetraisopropyl-disiloxanyl group, abbreviated TIPDS, that can protect two alcohol groups in a molecule.

(a) The TIPDS group is somewhat hindered around the Siatoms by the isopropyl groups. Which OHis more likely to react first with TIPDS chloride? Show the product with the TIPDS group on one oxygen.

(b) Once the TIPDS group is attached at the first oxygen, it reaches around to the next closest oxygen. Show the final product with two oxygens protected.

(c) The unprotected hydroxy group can now undergo reactions without affecting the protected oxygens. Show the product after the protected nucleoside from (b) is treated with tosyl chloride and pyridine, followed by NaBr, ending with deprotection with Bu4NF.

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