Epichlorohydrin (1) is an epoxide used in the production

Chapter 1, Problem 1.7

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Epichlorohydrin (1) is an epoxide used in the production of plastic, epoxy glues, and resins (reactions of epoxides will be discussed in Chapter 14). When epichlorohydrin is treated with phenol (2), two products are formed (3 and 4). At room temperature, these liquid products are difficult to separate from each other, but upon heating, these compounds are easily separated from one another. Explain these observations (Tetrahedron 2006, 62, 1096810979). C C O C Cl H H H H H C C HO C Cl H H H C C C C C C H H H H H OH NaOH, heat O C C C C C C H H H H H H H + C C O C O H H H H H C C C C C C H H H H H 1 2 3 4

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