Ethers and Epoxides; Thiols and Sulfides

Ethers and Epoxides; Thiols and Sulfides
Organic Chemistry Second Edition David Klein Chapter 14 Ethers and Epoxides; Thiols and Sulfides Copyright © 2015 John Wiley & Sons, Inc. All rights reserved.

Please note: If your clicker system can only hold 5 multiple choice answers, we have provided ‘alternate answers’ for those questions in which the author originally had more than 5 choices. These answers appear on the slides with a green background. If your clicker system can hold more than 5 multiple choice answers, please delete the slides with the green backgrounds, and use the original answers the author has listed. Copyright © 2015 John Wiley & Sons, Inc. All rights reserved.

Section: What is the correct IUPAC name for the following structure? a. secbutyl propyl ether b. isobutyl sec-butyl ether c. sec-butyl isopropyl ether d. isopropyl isobutyl ether Copyright © 2015 John Wiley & Sons, Inc. All rights reserved.

For more examples of this type of problem, see SkillBuilder 14.1.
Answer: c. For more examples of this type of problem, see SkillBuilder 14.1. Copyright © 2015 John Wiley & Sons, Inc. All rights reserved.

Section: Rank the following compounds from lowest to highest boiling point based on your knowledge of intermolecular forces. 5<2<4<3<1 2<5<3<4<1 5<4<2<3<1 2<5<3<1<4 All have similar molar masses, so the boiling points are similar Copyright © 2015 John Wiley & Sons, Inc. All rights reserved.

Answer: b. The presence of the oxygen in ethers makes them more polar than the corresponding alkanes, and therefore have stronger intermolecular forces and boiling points. They are still not as high boiling as similar alcohols, which are held in proximity by hydrogen bonding. Copyright © 2015 John Wiley & Sons, Inc. All rights reserved.

Section: Crown ethers are examples of phase-transfer catalysts (PTC). PTC takes the ionic nucleophile and brings it into the organic layer. There they pick up the leaving group anion and bring it back into the aqueous layer. The leaving group is transferred for another nucleophile and the whole process continues. PTC allows SN2 reactions to occur in the best possible solvent, ___ . a. polar protic b. polar aprotic c. nonpolar protic d. nonpolar aprotic Copyright © 2015 John Wiley & Sons, Inc. All rights reserved.

Section: 14.5 4. What is the product of the following reaction?
Copyright © 2015 John Wiley & Sons, Inc. All rights reserved.

Section: 14.5 6. Which of the following reactions will not occur as written?
2 3 1&2 3&4 Copyright © 2015 John Wiley & Sons, Inc. All rights reserved.

Answer: e. Williamson synthesis of ethers does not work with 3o alkyl halides and halogenated benzene rings. For more examples of this type of problem, see SkillBuilder 14.2. Copyright © 2015 John Wiley & Sons, Inc. All rights reserved.

Section: 14.5 7. What is the correct order of reagents needed for the following transformation?
1) Hg(OAc)2, THF:H2O 2) NaBH4, OH– 1) BH3:THF 2) H2O2, OH– 1) Hg(OAc)2, CH3CH2OH 2) NaBH4, OH– 1) MCPBA 2) H+ 3) NaH 4) Ethyl iodide Copyright © 2015 John Wiley & Sons, Inc. All rights reserved.

Answer: c. If the Oxymercuration-Demercuration reaction uses an alcohol instead of water it will produce an ether and be called the Alkoxymercuration-Demercuration reaction. For more examples of this type of problem, see SkillBuilder 14.2. Copyright © 2015 John Wiley & Sons, Inc. All rights reserved.

Section: 14.6 8. What are the product(s) of the following reaction?

Alternate Answers: Section: 14. 6 8
Alternate Answers: Section: What are the product(s) of the following reaction? a, d a, e b, e c, e c, f Copyright © 2015 John Wiley & Sons, Inc. All rights reserved.

Section: 14.7 9. What are the product(s) of the following reaction??

Answer: c. Ethers will react with strong mineral acids to form halides, but when a phenyl ring is in the alpha position, the C-O bond is too stable, and a phenol and an alkyl halide result. Copyright © 2015 John Wiley & Sons, Inc. All rights reserved.

Section: 14.7 10. What is the correct IUPAC name for the following structure?
a. 2-ethyl-1-methy-1,2-dipropyloxirane b. 1-ethyl-2-methy-1,2-dipropyloxirane c. 4-ethyl-5-methyl-4,5-epoxyoctane d. 5-ethyl-4-methyl-4,5-epoxyoctane Copyright © 2015 John Wiley & Sons, Inc. All rights reserved.

Section: 14.8 11. Which of the following will produce the epoxide below?

Alternate Answers: Section: 14. 8 11
Alternate Answers: Section: Which of the following will produce the epoxide below? a, b a, c b, c b, d c, d Copyright © 2015 John Wiley & Sons, Inc. All rights reserved.

Answer: a. Strong nucleophiles attack epoxides at the less substituted position via anti attack. For more examples of this type of problem, see SkillBuilder 14.4. Copyright © 2015 John Wiley & Sons, Inc. All rights reserved.

Answer: a. Addition of an acid to an epoxide produces the anti-Markovnikov, anti addition product. For more examples of this type of problem, see SkillBuilder 14.5. Copyright © 2015 John Wiley & Sons, Inc. All rights reserved.

Section: Which of the following reagents will attack the epoxide ring at the carbon labeled C1? CH3CH2MgBr, Et2O NaOEt NaH, hexane H3O+ None of the above Copyright © 2015 John Wiley & Sons, Inc. All rights reserved.

Answer: e. For primary and secondary epoxide, acid attack occurs at the less substituted position, as sterics is a bigger factor than partial carbocation structure. All of the strong nucleophiles attack at the less substituted position. For more examples of this type of problem, see SkillBuilder 14.5. Copyright © 2015 John Wiley & Sons, Inc. All rights reserved.

Alternate Answer: Section: 14. 11 19
Alternate Answer: Section: 14.11 19. What is the correct order of reagents needed for the following transformation? a, b, f a, b, g a, b, h a, b, i a, c, g Copyright © 2015 John Wiley & Sons, Inc. All rights reserved.

Section: 14.11 20. What is the product of the following reaction sequence?

Answer: a. Addition of peroxides to sulfides lead to the formation of the highly oxidized sulfones. For more practice with sulfur compounds see Conceptual Checkpoint 14.23 Copyright © 2015 John Wiley & Sons, Inc. All rights reserved.

Alternate Answer: Section: 14.11 21. What is the correct order of reagents needed for the following transformation? a, d a, e a, c, d a, c, e a, d, e Copyright © 2015 John Wiley & Sons, Inc. All rights reserved.

a. 1) Sodium Methoxide/Methanol 2) MCPBA 3) NaBr b. 1) NaH, Ts-Cl 2) Sodium Methoxide/Methanol 3) MCPBA 4) NaBr c. 1) NaH, Ts-Cl 2) Sodium Methoxide/Methanol 3) MCPBA 4) HBr d. 1) Sodium Methoxide/Methanol 2) MCPBA 3) HBr Copyright © 2015 John Wiley & Sons, Inc. All rights reserved.

Answer: b. Alcohol must be converted to a good leaving group before it is eliminated. MCPBA followed by base such as NaBr gives anti addition where the Br ends up on the less substituted carbon and the OH ends up on the more substituted carbon. For more examples of this type of problem, see SkillBuilder 14.6. Copyright © 2015 John Wiley & Sons, Inc. All rights reserved.

Alternate Answer: Section: What is the correct order of reagents needed for the following transformation? a, f, e, d a, g, e, d a, h, e, d b, f, e, d b, g, e, d Copyright © 2015 John Wiley & Sons, Inc. All rights reserved.

Section: 14.12 24. What would be the major product of the following synthetic sequence?

Ethers and Epoxides; Thiols and Sulfides

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