tb18 - Chaoter 18 - Ethers and Eooxides; Thiols and...

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Chaoter 18 - Ethers and Eooxides; Thiols and Sulfides Draw structures corresponding to each ofthe following names. 1. tetrahydrofuran Answer: Q 2. 12-crown-4 Answer: /\ rO O J --0 ° LJ 3. 1-isopropoxycyclopentene Answer: ~o 6 4. allyl benzyl ether Answer: () ~ I ° ~ 5. diethylether Answer: CH3CH2- 0- CH2CH3 6. 3-methyl-l-butanethiol Answer: iSH Test Itemsfor McMurry's Organic Chemistry, Seventh Edition 181
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7. cyclopropyl ethyl sulfide Answer: l>-- S- aI2aI3 Provide correct IUP AC names for each of the structures below. 8. Answer: m-chloroanisole or m-chloromethoxybenzene or (m-chlorophenyl) methyl ether 9. aI3 I H3C- C- aI2- 0- aI2aI3 I aI3 Answer: l-ethoxy-2,2-dimethylpropane or ethyl neopentyl ether 10. o-s-o Answer: dicyclohexyl sulfide Consider the reaction below to answer the following questions. (y °H (y °-aI3 l.NaH 2. CH3I, ether~ 11. Write the complete stepwise mechanism for the reaction. Show all intermediate structures and all electron flow with arrows. Answer: (""yl;Jl'\'H- ~2:~C\ ~o--rn3 U ~U ~U +NaI + H2 182 Chapter 18: Ethers and Epoxides; Thio/s and Sulfides
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12. Mechanistically, the Williamson ether synthesis outlined above is: a. b. c. d. an E I process an SNI process an E2 process an SN2 process Answer: d 13. Alternatively, cyclopentyl methyl ether may be synthesized from cyclopentene. Outline a synthesis of cyclopentyl methyl ether from cyclopentene. Answer: 0 Hg(02CCF3h . CH30H Q Hg02CCF3 NaBIf.t . OCR3 QH OCR3 14. Diphenyl ether is inert to cleavage by HI or HBr. Explain. o- ° -o ~ ~ /; - HX .. Answer: no reaction Acidic ether cleavages are typical nucleophilic substitution reactions that take place by either an SNI or SN2pathway. Diaryl ethers like diphenyl ether are inert under ordinary acidic conditions because the generation of an aryl cation is an S N I process that is energetically unfavorable, and "back-side" attack at the ring carbon bound to oxygen is sterically unfavorable.
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tb18 - Chaoter 18 - Ethers and Eooxides; Thiols and...

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