1. Chapter 16 Ethers, Epoxides, and Sulfides
Dr. Wolf's CHM 201 & 202
16-1 2

2. Nomenclature of Ethers, Epoxides, and Sulfides
Dr. Wolf's CHM 201 & 202
16-2 2

3. Substitutive IUPAC Names of Ethers
name as alkoxy derivatives of alkanes
CH3OCH2 CH3
methoxyethane
CH3CH2OCH2CH2CH2Cl
1-chloro-3-ethoxypropane
CH3CH2OCH2 CH3
ethoxyethane
Dr. Wolf's CHM 201 & 202
16-3 3

4. Functional Class IUPAC Names of Ethers
name the groups attached to oxygen in alphabetical order as separate words; "ether" is last word
CH3OCH2 CH3
ethyl methyl ether
CH3CH2OCH2CH2CH2Cl
3-chloropropyl ethyl ether
CH3CH2OCH2 CH3
diethyl ether
Dr. Wolf's CHM 201 & 202
16-4 3

5. Substitutive IUPAC Names of Sulfides
name as alkylthio derivatives of alkanes
CH3SCH2 CH3
methylthioethane
SCH3
(methylthio)cyclopentane
CH3CH2SCH2 CH3
ethylthioethane
Dr. Wolf's CHM 201 & 202
16-5 3

6. Functional Class IUPAC Names of Sulfides
analogous to ethers, but replace “ether” as last word in the name by “sulfide.”
CH3SCH2 CH3
ethyl methyl sulfide
SCH3
cyclopentyl methyl sulfide
CH3CH2SCH2 CH3
diethyl sulfide
Dr. Wolf's CHM 201 & 202
16-6 3

7. Oxirane (Ethylene oxide) Oxetane Oxolane (tetrahydrofuran)
Names of Cyclic Ethers O O O
Oxirane (Ethylene oxide)
Oxetane
Oxolane (tetrahydrofuran) O O O
Oxane (tetrahydropyran)
1,4-Dioxane
Dr. Wolf's CHM 201 & 202
16-7 3

8. Names of Cyclic Sulfides
Thiirane
Thietane
Thiolane S
Thiane
Dr. Wolf's CHM 201 & 202
16-8 3

9. Structure and Bonding in Ethers and Epoxides
bent geometry at oxygen analogous to water and alcohols, i.e. sp3 hybidization
Dr. Wolf's CHM 201 & 202
16-9 8

10. Bond angles at oxygen are sensitive to steric effectsH H
CH3 H
105°
108.5° O
(CH3)3C O
C(CH3)3
CH3
CH3
112°
132°
Dr. Wolf's CHM 201 & 202
16-10 9

11. An oxygen atom affects geometry in much the same way as a CH2 group
most stable conformation of diethyl ether resembles pentane
Dr. Wolf's CHM 201 & 202
16-11 10

12. An oxygen atom affects geometry in much the same way as a CH2 group
most stable conformation of tetrahydropyran resembles cyclohexane
Dr. Wolf's CHM 201 & 202
16-12 10

13. Physical Properties of Ethers
Dr. Wolf's CHM 201 & 202
16-13 11

14. Ethers resemble alkanes more than alcohols with respect to boiling point
Intermolecular hydrogen bonding possible in alcohols; not possible in alkanes or ethers.
36°C
35°C O
117°C OH
Dr. Wolf's CHM 201 & 202
16-14 12

15. solubility in water (g/100 mL)
Ethers resemble alcohols more than alkanes with respect to solubility in water
solubility in water (g/100 mL)
very small
7.5
Hydrogen bonding to water possible for ethers and alcohols; not possible for alkanes. O 9 OH
Dr. Wolf's CHM 201 & 202
16-15 12

16. Crown Ethers
Dr. Wolf's CHM 201 & 202
16-16 13

17. structure cyclic polyethers derived from repeating —OCH2CH2— units
Crown Ethers
structure cyclic polyethers derived from repeating —OCH2CH2— units
properties form stable complexes with metal ions
applications synthetic reactions involving anions
Dr. Wolf's CHM 201 & 202
16-17 14

18. negative charge concentrated in cavity inside the molecule
18-Crown-6 O
negative charge concentrated in cavity inside the molecule
Dr. Wolf's CHM 201 & 202
16-18 15

19. negative charge concentrated in cavity inside the molecule
18-Crown-6 O
negative charge concentrated in cavity inside the molecule
Dr. Wolf's CHM 201 & 202
16-19 15

20. forms stable Lewis acid/Lewis base complex with K+
18-Crown-6 O K+
forms stable Lewis acid/Lewis base complex with K+
Dr. Wolf's CHM 201 & 202
16-20 15

21. forms stable Lewis acid/Lewis base complex with K+
18-Crown-6 O K+
forms stable Lewis acid/Lewis base complex with K+
Dr. Wolf's CHM 201 & 202
16-21 15

22. Ion-Complexing and Solubility
K+F–
not soluble in benzene
Dr. Wolf's CHM 201 & 202
16-22 16

23. Ion-Complexing and Solubility
K+F–
benzene
add 18-crown-6
Dr. Wolf's CHM 201 & 202
16-23 16

24. Ion-Complexing and SolubilityF– K+
benzene
18-crown-6 complex of K+ dissolves in benzene
Dr. Wolf's CHM 201 & 202
16-24 16

25. Ion-Complexing and SolubilityK+
benzene
F– carried into benzene to preserve electroneutrality + F–
Dr. Wolf's CHM 201 & 202
16-25 16

26. Application to organic synthesis
Complexaton of K+ by 18-crown-6 "solubilizes" salt in benzene
Anion of salt is in a relatively unsolvated state in benzene (sometimes referred to as a "naked anion")
Unsolvated anion is very reactive
Only catalytic quantities of 18-crown-6 are needed
Dr. Wolf's CHM 201 & 202
16-26 20

27. Example KF CH3(CH2)6CH2Br CH3(CH2)6CH2F 18-crown-6 benzene (92%) 16-27
Dr. Wolf's CHM 201 & 202
16-27 20

28. Preparation of Ethers
Dr. Wolf's CHM 201 & 202
16-28 21

29. Acid-Catalyzed Condensation of Alcohols*
2CH3CH2CH2CH2OH
H2SO4, 130°C
CH3CH2CH2CH2OCH2CH2CH2CH3
(60%)
*Discussed earlier in Section 15.7
Dr. Wolf's CHM 201 & 202
16-29 10

30. Addition of Alcohols to Alkenes
(CH3)2C=CH2 + CH3OH
(CH3)3COCH3
tert-Butyl methyl ether
Dr. Wolf's CHM 201 & 202
16-30 23

31. The Williamson Ether Synthesis
Think SN2!
primary alkyl halide + alkoxide nucleophile
Dr. Wolf's CHM 201 & 202
16-31 24

32. Example CH3CH2CH2CH2ONa + CH3CH2I CH3CH2CH2CH2OCH2CH3 + NaI (71%)
Dr. Wolf's CHM 201 & 202
16-32 25

33. Another Example CH2Cl + CH3CHCH3 ONa CH2OCHCH3 CH3 (84%) 16-33 26
Dr. Wolf's CHM 201 & 202
16-33 26

34. Alkyl halide must be primary
Another Example
Alkoxide ion can be derived from primary, secondary, or tertiary alcohol
Alkyl halide must be primary
CH2Cl +
CH3CHCH3
ONa
CH2OCHCH3
CH3
(84%)
Dr. Wolf's CHM 201 & 202
16-34 26

35. Origin of Reactants CH3CHCH3 CH2OH OH HCl Na CH2Cl + CH3CHCH3 ONa
CH2OCHCH3
(84%)
CH3
Dr. Wolf's CHM 201 & 202
16-35 26

36. What happens if the alkyl halide is not primary?
CH2ONa +
CH3CHCH3 Br
Dr. Wolf's CHM 201 & 202
16-36 27

37. What happens if the alkyl halide is not primary?
CH2ONa +
CH3CHCH3 Br
CH2OH +
H2C
CHCH3
Elimination by the E2 mechanism becomes the major reaction pathway.
Dr. Wolf's CHM 201 & 202
16-37 27

38. Reactions of Ethers: A Review and a Preview
Dr. Wolf's CHM 201 & 202
16-38 28

39. Summary of reactions of ethers
No reactions of ethers encountered to this point.
Ethers are relatively unreactive.
Their low level of reactivity is one reason why ethers are often used as solvents in chemical reactions.
Ethers oxidize in air to form explosive hydroperoxides and peroxides.
Dr. Wolf's CHM 201 & 202
16-39 27

40. Acid-Catalyzed Cleavage of Ethers
Dr. Wolf's CHM 201 & 202
16-40 29

41. Example CH3CHCH2CH3 HBr CH3CHCH2CH3 + CH3Br heat OCH3 Br (81%) 16-41
Dr. Wolf's CHM 201 & 202
16-41 31

42. Mechanism CH3CHCH2CH3 O CH3 H Br CH3CHCH2CH3 O CH3 H + • • •• •• • •
Dr. Wolf's CHM 201 & 202
16-42 31

43. Mechanism CH3CHCH2CH3 O CH3 H Br CH3CHCH2CH3 O H CH3CHCH2CH3 O CH3 H +
• • ••
CH3 H Br
• • ••
CH3CHCH2CH3 O H
• • ••
CH3CHCH2CH3 O
CH3 H + •• Br – ••
• •
• • ••
CH3 Br ••
Dr. Wolf's CHM 201 & 202
16-43 31

44. Mechanism CH3CHCH2CH3 O CH3CHCH2CH3 Br CH3 H Br HBr CH3CHCH2CH3 O H
• • ••
CH3CHCH2CH3 Br
CH3 H Br
• • ••
HBr
CH3CHCH2CH3 O H
• • ••
CH3CHCH2CH3 O
CH3 H + •• Br – ••
• •
• • ••
CH3 Br ••
Dr. Wolf's CHM 201 & 202
16-44 31

45. Cleavage of Cyclic EthersHI
ICH2CH2CH2CH2I
150°C
(65%)
Dr. Wolf's CHM 201 & 202
16-45 32

46. Mechanism ICH2CH2CH2CH2I O HI + O H •• •• •• 16-46 32
Dr. Wolf's CHM 201 & 202
16-46 32

47. Mechanism ICH2CH2CH2CH2I O HI – I I + O O H H •• •• •• •• • • •• ••
Dr. Wolf's CHM 201 & 202
16-47 32

48. Mechanism O ICH2CH2CH2CH2I HI HI I – H O + I O H •• •• •• •• • • •• ••
Dr. Wolf's CHM 201 & 202
16-48 32

49. Preparation of Epoxides: A Review and a Preview
Dr. Wolf's CHM 201 & 202
16-49 1

50. Preparation of Epoxides
Epoxides are prepared by two major methods. Both begin with alkenes.
reaction of alkenes with peroxy acids (Section 6.19)
conversion of alkenes to vicinal halohydrins, followed by treatment with base (Section 16.10)
Dr. Wolf's CHM 201 & 202
16-50 30

51. Conversion of Vicinal Halohydrins to Epoxides
Dr. Wolf's CHM 201 & 202
16-51 2

52. Example H OH Br H
NaOH O
H2O H
(81%)
Dr. Wolf's CHM 201 & 202
16-52 5

53. Example H H OH NaOH O H2O Br H (81%) – O via: H H Br •• • • • • • •
Dr. Wolf's CHM 201 & 202
16-53 5

54. Epoxidation via Vicinal HalohydrinsBr
Br2
H2O OH
anti addition
Dr. Wolf's CHM 201 & 202
16-54 3

55. Epoxidation via Vicinal HalohydrinsBr
Br2
NaOH
H2O O OH
anti addition
inversion
corresponds to overall syn addition of oxygen to the double bond
Dr. Wolf's CHM 201 & 202
16-55 3

56. Epoxidation via Vicinal HalohydrinsBr
H3C
Br2 H
NaOH
H3C H
CH3 H
H2O H O
CH3 OH
anti addition
inversion
corresponds to overall syn addition of oxygen to the double bond
Dr. Wolf's CHM 201 & 202
16-56 3

57. Epoxidation via Vicinal HalohydrinsBr
H3C
Br2
H3C H H
NaOH
H3C H H
CH3
CH3 H
H2O H O
CH3 OH
anti addition
inversion
corresponds to overall syn addition of oxygen to the double bond
Dr. Wolf's CHM 201 & 202
16-57 3

58. Reactions of Epoxides: A Review and a Preview
Dr. Wolf's CHM 201 & 202
16-58 6

59. Reactions of Epoxides
All reactions involve nucleophilic attack at carbon and lead to opening of the ring.
An example is the reaction of ethylene oxide with a Grignard reagent (discussed in Section as a method for the synthesis of alcohols).
Dr. Wolf's CHM 201 & 202
16-59 7

60. Reaction of Grignard Reagents with Epoxides
MgX R
H2C
CH2 O
CH2
CH2
OMgX
H3O+
RCH2CH2OH
Dr. Wolf's CHM 201 & 202
16-60 9

61. Example CH2 CH2MgCl H2C + O 1. diethyl ether 2. H3O+ CH2CH2CH2OH (71%)
Dr. Wolf's CHM 201 & 202
16-61 29

62. In general...
Reactions of epoxides involve attack by a nucleophile and proceed with ring-opening. For ethylene oxide:
H2C
CH2 O
Nu—H +
Nu—CH2CH2O—H
Dr. Wolf's CHM 201 & 202
16-62 10

63. In general...
For epoxides where the two carbons of the ring are differently substituted:
Nucleophiles attack here when the reaction is catalyzed by acids:
Anionic nucleophiles attack here:
CH2 O C R H
Dr. Wolf's CHM 201 & 202
16-63 10

64. Nucleophilic Ring-Opening Reactions of Epoxides
Dr. Wolf's CHM 201 & 202
16-64 9

65. Example O H2C CH2 NaOCH2CH3 CH3CH2OH CH3CH2O CH2CH2OH (50%) 16-65 11
Dr. Wolf's CHM 201 & 202
16-65 11

66. Mechanism CH3CH2 O – O H2C CH2 • • •• • • •• 16-66 12
Dr. Wolf's CHM 201 & 202
16-66 12

67. Mechanism CH3CH2 O – O H2C CH2 – CH3CH2 O CH2CH2 • • •• • • •• •• • •
Dr. Wolf's CHM 201 & 202
16-67 12

68. Mechanism CH3CH2 O – O H2C CH2 O CH2CH3 H – CH3CH2 O CH2CH2 • • •• • •
Dr. Wolf's CHM 201 & 202
16-68 12

69. Mechanism CH3CH2 O – O H2C CH2 O CH2CH3 H – CH3CH2 O CH2CH2 O CH2CH3 –••
• • – O
H2C
CH2
• • •• O
CH2CH3
• • H •• –
CH3CH2 O ••
CH2CH2 •• •• •• •• O
CH2CH3
• • – •• ••
CH3CH2 O
CH2CH2 O H •• •• ••
Dr. Wolf's CHM 201 & 202
16-69 12

70. Example O H2C CH2 KSCH2CH2CH2CH3 ethanol-water, 0°C CH2CH2OH
CH3CH2CH2CH2S
(99%)
Dr. Wolf's CHM 201 & 202
16-70 11

71. Inversion of configuration at carbon being attacked by nucleophile
Stereochemistry
OCH2CH3 O H
NaOCH2CH3
CH3CH2OH H H OH
(67%)
Inversion of configuration at carbon being attacked by nucleophile
Suggests SN2-like transition state
Dr. Wolf's CHM 201 & 202
16-71 11

72. (70%) Stereochemistry H3C CH3 H NH3 H OH O H2N H H2O H H3C CH3
Inversion of configuration at carbon being attacked by nucleophile
Suggests SN2-like transition state
Dr. Wolf's CHM 201 & 202
16-72 18

73. (70%) d- Stereochemistry H3C CH3 H NH3 H OH O H2N H H2O H H3C CH3 H3C
Dr. Wolf's CHM 201 & 202
16-73 18

74. Anionic nucleophile attacks less-crowded carbon
CH3CH
CCH3
CH3 OH
CH3O C H
H3C
CH3 O
NaOCH3
CH3OH
(53%)
consistent with SN2-like transition state
Dr. Wolf's CHM 201 & 202
16-74 19

75. Anionic nucleophile attacks less-crowded carbon
MgBr + O
H2C
CHCH3
1. diethyl ether
2. H3O+
CH2CHCH3 OH
(60%)
Dr. Wolf's CHM 201 & 202
16-75 15

76. Lithium aluminum hydride reduces epoxides
H2C
CH(CH2)7CH3
Hydride attacks less-crowded carbon
1. LiAlH4, diethyl ether
2. H2O OH
H3C
CH(CH2)7CH3
(90%)
Dr. Wolf's CHM 201 & 202
16-76 16

77. Acid-Catalyzed Ring-Opening Reactions of Epoxides
Dr. Wolf's CHM 201 & 202
16-77 22

78. Example O H2C CH2 CH3CH2OH CH3CH2OCH2CH2OH H2SO4, 25°C (87-92%)
CH3CH2OCH2CH2OCH2CH3 formed only on heating and/or longer reaction times
Dr. Wolf's CHM 201 & 202
16-78 11

79. BrCH2CH2Br formed only on heating and/or longer reaction times
Example O
H2C
CH2
HBr
BrCH2CH2OH
10°C
(87-92%)
BrCH2CH2Br formed only on heating and/or longer reaction times
Dr. Wolf's CHM 201 & 202
16-79 11

80. Mechanism O H2C CH2 O H2C CH2 + H Br – H Br • • • • •• • • • • •• ••
Dr. Wolf's CHM 201 & 202
16-80 12

81. Mechanism Br – O H2C CH2 O H2C CH2 + H H Br O Br CH2CH2 H • • •• • •
Dr. Wolf's CHM 201 & 202
16-81 12

82. Figure 16.6 Acid-Catalyzed Hydrolysis of Ethylene Oxide
Step 1
H2C
CH2
H2C
CH2 + O O O
• • H +
• • H
• • •• H O
• •
• • H
Dr. Wolf's CHM 201 & 202
16-82 12

83. Figure 16.6 Acid-Catalyzed Hydrolysis of Ethylene Oxide
Step 2
• • O
H2C
CH2 •• + H
• • + O
CH2CH2 H •• ••
Dr. Wolf's CHM 201 & 202
16-83 12

84. Figure 16.6 Acid-Catalyzed Hydrolysis of Ethylene Oxide
• • H +
Step 3
• • O
CH2CH2 H O ••
• • H
• • + O
CH2CH2 H •• •• •• ••
Dr. Wolf's CHM 201 & 202
16-84 12

85. Acid-Catalyzed Ring Opening of Epoxides
Characteristics:
nucleophile attacks more substituted carbon of protonated epoxide
inversion of configuration at site of nucleophilic attack
Dr. Wolf's CHM 201 & 202
16-85 30

86. Nucleophile attacks more-substituted carbon
OCH3 C H
H3C
CH3 O
CH3OH
CH3CH
CCH3 C
H2SO4 OH
CH3
(76%)
consistent with carbocation character at transition state
Dr. Wolf's CHM 201 & 202
16-86 19

87. Nucleophile attacks more-substituted carbon
OCH3 C H
H3C
CH3 OH
CH3OH d+ d+
CH3CH
CCH3 C
H2SO4 OH
CH3 d+
(76%)
consistent with carbocation character at transition state
Dr. Wolf's CHM 201 & 202
16-86b 19

88. Inversion of configuration at carbon being attacked by nucleophile
Stereochemistry H O H OH
HBr H Br
(73%)
Inversion of configuration at carbon being attacked by nucleophile
Dr. Wolf's CHM 201 & 202
16-87 11

89. (57%) Stereochemistry H3C CH3 H CH3OH H OH O CH3O H H2SO4 H H3C CH3
Inversion of configuration at carbon being attacked by nucleophile
Dr. Wolf's CHM 201 & 202
16-88 18

90. Stereochemistry H3C CH3 H CH3OH H OH O CH3O H H2SO4 H H3C CH3 H3C H d+
Dr. Wolf's CHM 201 & 202
16-89 18

91. anti-Hydroxylation of Alkenes
CH3COOH O H
H2O
HClO4 H OH H OH
(80%)
Dr. Wolf's CHM 201 & 202
16-90 35

92. Epoxides in Biological Processes
Dr. Wolf's CHM 201 & 202
16-91 1

93. Naturally Occurring Epoxides
are common
are involved in numerous biological processes
Dr. Wolf's CHM 201 & 202
16-92

94. Biosynthesis of EpoxidesC + O2 H+ +
NADH
enzyme C C +
H2O +
NAD+ O
enzyme-catalyzed oxygen transfer from O2 to alkene
enzymes are referred to as monooxygenases
Dr. Wolf's CHM 201 & 202
16-93

95. Example: biological epoxidation of squalene
O2, NADH monoxygenase O
this reaction is an important step in the biosynthesis of cholesterol
Dr. Wolf's CHM 201 & 202
16-94

96. Preparation of Sulfides
Dr. Wolf's CHM 201 & 202
16-95 1

97. – R S R' R S + R' X NaSCH3 CH3CHCH CH2 Cl CH3CHCH CH2 SCH3 methanol
Preparation of RSR'
prepared by nucleophilic substitution (SN2) – ••
• • •• R S R' R S + R' X
NaSCH3
CH3CHCH
CH2 Cl
CH3CHCH
CH2
SCH3
methanol
Dr. Wolf's CHM 201 & 202
16-96

98. Oxidation of Sulfides: Sulfoxides and Sulfones
Dr. Wolf's CHM 201 & 202
16-97 1

99. R S R' O – + O – ++ R S R' R S R' O – sulfide sulfoxide sulfone
Oxidation of RSR' •• R S R' O
• • – + O
• • •• – ++ •• R S R' R S R' O
• • •• –
sulfide
sulfoxide
sulfone
either the sulfoxide or the sulfone can be isolated depending on the oxidizing agent and reaction conditions
Dr. Wolf's CHM 201 & 202
16-98

100. SCH3 O – + SCH3 NaIO4 water (91%) Example •• • • ••
Sodium metaperiodate oxidizes sulfides to sulfoxides and no further.
Dr. Wolf's CHM 201 & 202
16-99

101. SCH CH2 SCH O – ++ CH2 H2O2 (2 equiv) (74-78%) Example •• •• • •
1 equiv of H2O2 or a peroxy acid gives a sulfoxide, 2 equiv give a sulfone ••
SCH
CH2
SCH O
• • •• – ++
CH2
H2O2
(2 equiv)
(74-78%)
Dr. Wolf's CHM 201 & 202
16-100

102. Alkylation of Sulfides: Sulfonium Salts
Dr. Wolf's CHM 201 & 202
16-101 1

103. Sulfides can act as nucleophiles+ •• •• R S +
R" X R S
R" X–
• • R' R'
product is a sulfonium salt
Dr. Wolf's CHM 201 & 202
16-102

104. CH3I + CH3(CH2)10CH2SCH3 CH3(CH2)10CH2SCH3 I– CH3 Example 16-103
Dr. Wolf's CHM 201 & 202
16-103

105. Spectroscopic Analysis of Ethers
Dr. Wolf's CHM 201 & 202
16-104 1

106. Infrared Spectroscopy
C—O stretching: and 1150 cm-1 (strong)
Dr. Wolf's CHM 201 & 202
16-105 6

107. Figure 16.8 Infrared Spectrum of Dipropyl Ether
CH3CH2CH2OCH2CH2CH3
C—O—C
2000
3500
3000
2500
1000
1500
500
Wave number, cm-1
Dr. Wolf's CHM 201 & 202
16-106 8

108. d 1.4 ppm d 0.8 ppm d 0.8 ppm CH3 CH2 CH2 OCH2 CH2 CH3 d 3.2 ppm
1H NMR
H—C—O proton is deshielded by O; range is ca. d ppm.
d 1.4 ppm
d 0.8 ppm
d 0.8 ppm
CH3 CH2 CH2 OCH2 CH2 CH3
d 3.2 ppm
Dr. Wolf's CHM 201 & 202
16-107 6

109. CH3 CH2 CH2 OCH2 CH2 CH3 1 Chemical shift (d, ppm) 16-108 1.0 2.0 3.0
1.0
2.0
3.0
4.0
5.0
6.0
7.0
8.0
9.0
10.0
Chemical shift (d, ppm)
Dr. Wolf's CHM 201 & 202
16-108 1

110. Carbons of C—O—C appear in the range d 57-87 ppm.
13C NMR
Carbons of C—O—C appear in the range d ppm.
26.0 ppm O
68.0 ppm
Dr. Wolf's CHM 201 & 202
16-109

111. UV-VIS
Simple ethers have their absorption maximum at about 185 nm and are transparent to ultraviolet radiation above about 220 nm.
Dr. Wolf's CHM 201 & 202
16-110

112. + + Molecular ion fragments to give oxygen-stabilized carbocation.
Mass Spectrometry
Molecular ion fragments to give oxygen-stabilized carbocation. •+
CH3CH2O
CHCH2CH3
m/z 102 ••
CH3 + +
CH3CH2O CH
CH3CH2O
CHCH2CH3 •• ••
m/z 73
CH3
m/z 87
Dr. Wolf's CHM 201 & 202
16-111

113. End of Chapter 16