Reviewquestions_14

Reviewquestions_14 - Organic Chemistry, 6e (Wade) Chapter...

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Organic Chemistry, 6e (Wade) Chapter 14: Ethers, Epoxides, and Sulfides 1 6) Provide a structural representation of 2-ethoxypentane. Answer: Diff: 1 7) Provide a structural representation of isopropyl tert -butyl ether. Answer: (CH 3 ) 2 CHOC(CH 3 ) 3 Diff: 1 8) Provide a structural representation of 1,2-epoxybutane (also called 2-ethyloxirane). Answer: Diff: 1
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2 13) Propose a structure for the ether of formula C 4 H 10 O with the following 1 H NMR signals: δ 1.20 (triplet, 6H), δ 3.45 (quartet, 4H) (ppm). Answer: CH 3 CH 2 OCH 2 CH 3 Diff: 2 14) Propose a structure for the ether of formula C 4 H 10 O with the following 1 H NMR signals: δ 0.95 (triplet, 3H), 1.52 (multiplet, 2H), 3.30 (singlet, 3H), 3.40 (triplet, 2H) (ppm). Answer: CH 3 CH 2 CH 2 OCH 3 Diff: 2 15) Propose a structure for the ether of formula C 4 H 10 O with the following 1 H NMR signals: δ 1.13 (doublet, 6H), 3.30 (singlet, 3H), 3.65 (septet, 1H) (ppm). Answer: (CH 3 ) 2 CHOCH 3 Diff: 2 16) What is the chemical shift of the carbon bound to oxygen in ethers in 13 C NMR? Answer: δ 65 to δ 90 Diff: 3 17) The Williamson ether synthesis occurs by the __________ mechanistic pathway. Answer: S N 2 Diff: 1
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3 18) Show the best method for preparing methoxycyclopentane via the Williamson ether synthesis. Answer: Diff: 1 19) Show the best method for preparing 4-propoxytoluene via the Williamson ether synthesis. Answer: Diff: 2 20) Which pair of reagents would produce the highest yield of ( R )-2-ethoxybutane? A) sodium ( S )-2-butoxide + iodoethane B) sodium ( R )-2-butoxide + iodoethane C) sodium ethoxide + ( S )-2-iodobutane D) sodium ethoxide + ( R )-2-iodobutane E) Both B and C would work equally well. Answer: B Diff: 2 21) Provide the major organic product in the reaction below. CH 3 CH 2 CH 2 OH 2 1. Na 2. PhCH Br Answer: CH 3 CH 2 CH 2 OCH 2 Ph Diff: 1 22) Provide the major organic product in the reaction below. CH 3 CH 2 CH=CH 2 23 2 4 1. Hg(OAc) , CH CH OH 2. NaBH Answer: CH 3 CH 2 CHCH 3 O C H 2 CH 3 Diff: 2 23) Show the reagents necessary for the conversion of 1-bromo-1-methylcyclopentane to 1-ethoxy-1-methylcyclopentane.
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This note was uploaded on 03/18/2010 for the course DSAG asdg taught by Professor Asdg during the Spring '10 term at 東京国際大学.

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Reviewquestions_14 - Organic Chemistry, 6e (Wade) Chapter...

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