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natprod - EXPERIMENT Name NATURAL PRODUCTS AND ALKENES...

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Eugenol ‐ BP 254° C Limonene ‐ BP 175° C E XPERIMENT : N ATURAL P RODUCTS AND A LKENES Name _______________________________________ Instructor ____________________________________ Chem ____________ Section/Color _____________ _ Date ________________________________________ Laboratory Questions These questions are to be completed and turned in at the beginning of the pre-lab period. PRE-LAB QUESTIONS 1. Explain why the boiling point for a steam distillation will always be less than 100 ! C. (Review the theory of steam distillation.) 2. Explain why resorcinol (bp = 281 ! C) cannot be isolated from an aqueous mixture by steam distillation. Hint: Consider the structure and solubility properties of resorcinol (check Wikipedia: http://en.wikipedia.org/wiki/Main_Page ) versus the properties required for steam distillation. 3. The methylene chloride solution of clove oil contains a variety of organic compounds which remain insoluble in water even upon treatment with sodium hydroxide. This extraction thus separates these other compounds. Write the equation for the reaction of eugenol with sodium hydroxide and explain why the product is soluble in water. (Hint: Read McMurry, Section 17.3.)
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