Chapter 14 Homework PDF

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Book homework for Chapter 14, Wade Organic Chemistry, Dr. Hammer...

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Practice Problems: Chapter 14 Ethers, Epoxides, and Thioethers Chem 334, Spring 2017 1) What is the hybridization of the oxygen atom in dialkyl ethers? A) sp3 B) sp2 C) sp D) s E) p 3) Which has the higher boiling point, diethyl ether or butan-1-ol? Briefly explain.

4) Which of the following is not a property of ethers which makes them good solvents in organic reactions? A) They dissolve a wide range of polar substances. B) They have relatively high boiling points for their molecular weights. C) They are nonhydroxylic. D) They dissolve a wide range of nonpolar substances. E) They are normally unreactive toward strong bases. 9) Provide the structure of 3-methoxyfuran.

10) Provide a structural representation of 2-ethoxypentane.

12) Provide a structural representation of 1,2-epoxybutane (also called 2-ethyloxirane).

13) What is the correct IUPAC name for the following compound?

A) 3-methyl-3,4-epoxypentan-1-ol B) 5-hydroxy-3-methyl-2,3-epoxypentane C) 1-(2-hydroxyethyl)-1,2-dimethyloxirane D) 3,4-epoxy-3-methylpentan-1-ol

18) Provide a structural representation of oxetane.

23) Provide an acceptable name for the compound shown below.

30) Provide the major organic product of the following.

31) Provide the major organic product of the following.

34) Provide the major organic product of the following.

36) Show the best method for preparing methoxycyclopentane via the Williamson ether synthesis.

37) Provide the major organic product in the reaction below. CH3CH2CH2OH

à

38) Provide the major organic product in the reaction below.

42) Show the best method for preparing 4-propoxytoluene via the Williamson ether synthesis.

45) Provide the major organic product of the reaction shown below.

48) Provide the major organic product of the following.

49) Provide the necessary reagents to complete the following reaction.

54) Provide the major organic product of the following reactions.

55) Provide the major organic product of the following reactions.

59) Complete the following reaction by drawing a structure for the expected product.

62) Provide the major organic product in the reaction below.

66) Suggest a reasonable mechanism for the reaction shown below.

68) Provide the major organic product(s) in the reaction below.

71) Provide the major organic product of the following reactions.

73) Provide the major organic product of the reaction shown below.

77) Provide the major organic product in the reaction below.

82) Provide a common name for the following compound.

84) Provide the major organic product of the following.

85) Provide the major organic product of the following.

88) Provide the major organic product of the following reactions.

92) Provide the major organic product in the reaction below.

93) Provide the major organic product in the reaction below.

97) Provide the major organic product of the following reactions.

98) Provide the major organic product in the reaction below.

101) Provide the major organic product of the following.

102) Through what mechanism can a 1,2-halohydrin be converted into an epoxide? A) SN1 B) SN2 C) E2 D) electrophilic addition E) polymerization

103) Suggest a reasonable mechanism for the reaction shown below.

108) Use arrows to show correct electron flow in the mechanism for the reaction below. Include all intermediate structures correctly drawn with formal charges.

110) Draw the correct structure of the expected product of the following reaction.

112) Provide a structure for the expected product of the following reaction.

113) Provide the major organic product in the reaction below.

115) Provide the major organic product in the reaction below.

117) Show the reagents necessary to prepare the compound below from cyclohexanone.

119) Provide the major organic product in the reaction below.

122) Provide the major organic product in the reaction below.

126) Provide the major organic product of the following reactions.

Answer:

127) Provide the major organic product in the reaction below.

Practice Problems: Chapter 14 Ethers, Epoxides, and Thioethers Chem 334, Spring 2017 1) What is the hybridization of the oxygen atom in dialkyl ethers? A) sp3 B) sp2 C) sp D) s E) p Answer: A Diff: 1 Section: 14.2 3) Which has the higher boiling point, diethyl ether or butan-1-ol? Briefly explain. Answer: Butan-1-ol has the higher boiling point since intermolecular hydrogen bonding can occur. Molecules of diethyl ether are incapable of hydrogen bonding with each other. Diff: 1 Section: 14.2 4) Which of the following is not a property of ethers which makes them good solvents in organic reactions? A) They dissolve a wide range of polar substances. B) They have relatively high boiling points for their molecular weights. C) They are nonhydroxylic. D) They dissolve a wide range of nonpolar substances. E) They are normally unreactive toward strong bases. Answer: B Diff: 2 Section: 14.2 9) Provide the structure of 3-methoxyfuran. Answer:

Diff: 1 Section: 14.3 10) Provide a structural representation of 2-ethoxypentane. Answer:

Diff: 1 Section: 14.3

12) Provide a structural representation of 1,2-epoxybutane (also called 2-ethyloxirane). Answer:

Diff: 1 Section: 14.3 13) What is the correct IUPAC name for the following compound?

A) 3-methyl-3,4-epoxypentan-1-ol B) 5-hydroxy-3-methyl-2,3-epoxypentane C) 1-(2-hydroxyethyl)-1,2-dimethyloxirane D) 3,4-epoxy-3-methylpentan-1-ol Answer: A Diff: 2 Section: 14.3 18) Provide a structural representation of oxetane. Answer: Diff: 2 Section: 14.3 23) Provide an acceptable name for the compound shown below.

Answer: propylene oxide or methyloxirane Diff: 2 Section: 14.4 30) Provide the major organic product of the following.

Answer:

Diff: 2 Section: 14.4

31) Provide the major organic product of the following.

Answer:

Diff: 2 Section: 14.4 34) Provide the major organic product of the following.

Answer:

Diff: 3 Section: 14.4 36) Show the best method for preparing methoxycyclopentane via the Williamson ether synthesis. Answer:

Diff: 1 Section: 14.5 37) Provide the major organic product in the reaction below. CH3CH2CH2OH

à

Answer: CH3CH2CH2OCH2Ph Diff: 1 Section: 14.5 38) Provide the major organic product in the reaction below.

Answer:

Diff: 1 Section: 14.5 42) Show the best method for preparing 4-propoxytoluene via the Williamson ether synthesis. Answer:

Diff: 2 Section: 14.5 45) Provide the major organic product of the reaction shown below.

Answer:

Diff: 2 Section: 14.5 48) Provide the major organic product of the following.

Answer:

Diff: 2 Section: 14.5

49) Provide the necessary reagents to complete the following reaction.

Answer:

Diff: 3 Section: 14.5 54) Provide the major organic product of the following reactions.

Answer:

Diff: 2 Section: 14.6 55) Provide the major organic product of the following reactions.

Answer:

Diff: 2 Section: 14.6

59) Complete the following reaction by drawing a structure for the expected product.

Answer:

Diff: 2 Section: 14.6 62) Provide the major organic product in the reaction below.

Answer:

Diff: 2 Section: 14.7 66) Suggest a reasonable mechanism for the reaction shown below.

Answer:

or

Diff: 2 Section: 14.7

68) Provide the major organic product(s) in the reaction below.

Answer:

Diff: 1 Section: 14.8 71) Provide the major organic product of the following reactions.

Answer:

Diff: 2 Section: 14.8 73) Provide the major organic product of the reaction shown below.

Answer: Br(CH2)6Br Diff: 2 Section: 14.8 77) Provide the major organic product in the reaction below.

Answer: Diff: 3 Section: 14.8

82) Provide a common name for the following compound.

Answer: allyl ethyl sulfide Diff: 1 Section: 14.10 84) Provide the major organic product of the following.

Answer:

Diff: 2 Section: 14.10 85) Provide the major organic product of the following.

Answer:

Diff: 2 Section: 14.10 88) Provide the major organic product of the following reactions.

Answer:

Diff: 2 Section: 14.10 92) Provide the major organic product in the reaction below.

Answer:

Diff: 1 Section: 14.11 93) Provide the major organic product in the reaction below.

Answer:

Diff: 1 Section: 14.11 97) Provide the major organic product of the following reactions.

Answer:

Diff: 2 Section: 14.11 98) Provide the major organic product in the reaction below.

Answer:

Diff: 2 Section: 14.11 101) Provide the major organic product of the following.

Answer:

Diff: 2 Section: 14.11 102) Through what mechanism can a 1,2-halohydrin be converted into an epoxide? A) SN1 B) SN2 C) E2 D) electrophilic addition E) polymerization Answer: B Diff: 2 Section: 14.11 103) Suggest a reasonable mechanism for the reaction shown below.

Answer:

Diff: 2 Section: 14.11

108) Use arrows to show correct electron flow in the mechanism for the reaction below. Include all intermediate structures correctly drawn with formal charges.

Answer:

Diff: 3 Section: 14.12 110) Draw the correct structure of the expected product of the following reaction.

Answer:

Diff: 2 Section: 14.13 112) Provide a structure for the expected product of the following reaction.

Answer:

Diff: 3 Section: 14.13 113) Provide the major organic product in the reaction below.

Answer:

Diff: 2 Section: 14.14 115) Provide the major organic product in the reaction below.

Answer:

Diff: 2 Section: 14.14 117) Show the reagents necessary to prepare the compound below from cyclohexanone.

Answer:

1. CH3MgBr 2. conc. H2SO4 3. PhCO3H 4. CH3CH2ODiff: 3 Section: 14.14 119) Provide the major organic product in the reaction below.

Answer:

Diff: 3 Section: 14.14 122) Provide the major organic product in the reaction below.

Answer:

Diff: 2 Section: 14.15 126) Provide the major organic product of the following reactions.

Answer:

Diff: 2 Section: 14.15

127) Provide the major organic product in the reaction below.

Answer:

Diff: 2 Section: 14.15...