1. Solomons • Fryhle • Snyder
Organic Chemistry
ELEVENTH EDITION
Solomons • Fryhle • Snyder
Chapter 6
Ionic Reactions
Copyright © 2014 by John Wiley & Sons, Inc. All rights reserved.

6. Nucleophilic Substitution

9. SN2 Reaction

14. SN2 Kinetics

15. SN1 Reaction

19. SN1 Reaction Kinetics

21. SN2 Reaction Issues

57. SN1 Reaction Issues

73. Stabilities: B > C > A

85. These do not undergo either SN1 OR SN2 reactions

87. E2 Elimination Reactions
Go in one step like SN2 reactions, and involve negatively-charged bases; do not involve carbocations

96. E1 Elimination Reactions
Favored by neutral (uncharged) bases like SN1 reactions

105. Factors That Determine SN1, SN2, E1, and E2 Predominance
Negative nucleophile/base favors SN2 and E2
Primary electrophile favors SN2 over E2

106. Secondary electrophile and negative nucleophile favors E2

107. Tertiary electrophile with negative nucleophile favors E2

108. Raising temperature increases elimination preference

109. Primary electrophiles with negative unhindered nucleophiles give substitution even at elevated temperatures

110. Hindered nucleophiles increase the preference for elimination

111. Weak bases make elimination less favorable than substitution