In reference to cloth or fiber, the term acetate usually means cellulose acetate, a semisynthetic polymer made by treating cellulose with acetic anhydride. Cellulose acetate is spun into yarn by dissolving it in acetone or methylene chloride and forcing the solution through spinnerets into warm air, where the solvent evaporates.
(a) Draw the structure of cellulose acetate.
(b) Explain why cellulose acetate is soluble in organic solvents, even though cellulose is not.
(c) (A true story) An organic chemistry student wore a long-sleeved acetate blouse to the laboratory. She was rinsing a warm separatory funnel with acetone when the pressure rose and blew out the stopper. Her right arm was drenched with acetone, but she was unconcerned because acetone is not very toxic. About ten minutes later, the right arm of the student's blouse disintegrated into a pile of white fluff, leaving her with a ragged short sleeve and the tatters of a cuff remaining around her wrist. Explain how a substance as innocuous as acetone ruined the student's blouse.
(d) Predict what usually happens when students wear polyvinyl chloride shoes to the organic laboratory.