1,4-Dioxane is made commercially by the acid-catalyzed condensation of an alcohol. (a) Show what alcohol will undergo condensation, with loss of water, to give 1,4-dioxane.

Chemistry for Today: General, Organic, and Biochemistry
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Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
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Chapter14: Aldehydes And Ketones
Section: Chapter Questions
Problem 14.60E: Other addition reactions of aldehydes occur. Water, for example, adds to the carbonyl of...
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Can you please help do problem 14-5, only answer a.
ers, Epoxides, and Thioethers
Dioxin (previous page) is a common name for dibenzo-1,4-dioxane, which 1s
1,4-dioxane fused with two benzene rings The name dioxin is often used incorrectly in
the news media for 2,3,7,8-tetrachlorodibenzodioxin (TCDD), a toxic contaminant in
the synthesis of the herbicide called 2,4,5-T or Agent Orange. Surprisingly, TCDD has
been in the environment for many millions of vears because it is also formed in forest
fires. Most dioxins are toxic and carcinogenic (cause cancer) because they associate with
DNA and cause a misreading of the genetic code that can result in a genetic mutation.
3D
CH, —С—ОН
C.
Cl
Cl
2,4,5-trichlorophenoxyacetic acid
(2,4,5-T or Agent Orange)
2,3,7,8-tetrachlorodibenzodioxin
(TCDD, incorrectly "dioxin")
PROBLEM 14-5
1,4-Dioxane is made commercially by the acid-catalyzed condensation of an alcohol.
(a) Show what alcohol will undergo condensation, with loss of water, to give 1,4-dioxane.
(b) Propose a mechanism for this reaction.
PROBLEM 14-6
Name the following heterocyclic ethers.
(b)
(a)
(c)
CH(CH;),
CI
Transcribed Image Text:ers, Epoxides, and Thioethers Dioxin (previous page) is a common name for dibenzo-1,4-dioxane, which 1s 1,4-dioxane fused with two benzene rings The name dioxin is often used incorrectly in the news media for 2,3,7,8-tetrachlorodibenzodioxin (TCDD), a toxic contaminant in the synthesis of the herbicide called 2,4,5-T or Agent Orange. Surprisingly, TCDD has been in the environment for many millions of vears because it is also formed in forest fires. Most dioxins are toxic and carcinogenic (cause cancer) because they associate with DNA and cause a misreading of the genetic code that can result in a genetic mutation. 3D CH, —С—ОН C. Cl Cl 2,4,5-trichlorophenoxyacetic acid (2,4,5-T or Agent Orange) 2,3,7,8-tetrachlorodibenzodioxin (TCDD, incorrectly "dioxin") PROBLEM 14-5 1,4-Dioxane is made commercially by the acid-catalyzed condensation of an alcohol. (a) Show what alcohol will undergo condensation, with loss of water, to give 1,4-dioxane. (b) Propose a mechanism for this reaction. PROBLEM 14-6 Name the following heterocyclic ethers. (b) (a) (c) CH(CH;), CI
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