Arrow pushing in organic chemistry: an easy approach to understanding reaction mechanisms
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| Main Author: | |
|---|---|
| Format: | Book |
| Language: | English |
| Published: |
Hoboken, N.J.
Wiley
2008
|
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Item Description: | Includes index. |
| Physical Description: | XV, 301 S. graph. Darst. |
| ISBN: | 9780470171103 |
Staff View
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| 245 | 1 | 0 | |a Arrow pushing in organic chemistry |b an easy approach to understanding reaction mechanisms |c Daniel E. Levy |
| 264 | 1 | |a Hoboken, N.J. |b Wiley |c 2008 | |
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| 500 | |a Includes index. | ||
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Record in the Search Index
| _version_ | 1804138079090376704 |
|---|---|
| adam_text | Contents
PREFACE
xi
ACKNOWLEDGMENTS
xiii
ABOUT THE AUTHOR
xv
1.
Introduction
1
1.1
Definition of Arrow Pushing
1
1.2
Functional Groups
5
1.3
Nucleophiles and Leaving Groups
8
1.4
Summary
8
Problems
10
2.
Acids
19
2.1
What are Acids?
19
2.2
What is Resonance?
20
2.3
How is Acidity Measured?
23
2.4
Relative Acidities
25
2.5
Inductive Effects
29
2.6
Inductive Effects and Relative Acidities
31
2.7
Relative Acidities of Hydrocarbons
33
2.8
Summary 34
Problems
35
VII
VIH
CONTENTS
3.
Bases and Nucleophiles
45
3.1
What are Bases?
45
3.2
What are Nucleophiles?
50
3.3
Leaving Groups
54
3.4
Summary
55
Problems
56
4.
SN2 Substitution Reactions
65
4.1
What is an SN2 Reaction?
65
4.2
What are Leaving Groups?
67
4.3
Where Can SN2 Reactions Occur?
68
4.4
SN2 Reactions
71
4.5
Summary
73
Problems
74
5.
SN1 Substitution Reactions
83
5.1
What is an SN1 Reaction?
83
5.2
How are SN1 Reactions Initiated
84
5.3
The Carbocation
86
5.3.1
Molecular Structure and
Orbitals 86
5.3.2
Stability of Carbocations
90
5.4
Carbocation Rearrangements
92
5.4.1
1,2-Hydride Shifts
92
5.4.2 1,2-
Alkyl
Shifts
93
5.4.3
Preventing Side Reactions
95
5.5
Summary
96
Problems
97
6.
Elimination Reactions
101
6.1
El Eliminations
101
6.2
E2 Eliminations
104
6.3
How Do Elimination Reactions Work?
105
6.4
Summary
108
Problems
109
7.
Addition Reactions
115
7.1
Addition of Halogens to Double Bonds
115
7.2
Markovnikov s Rule
117
7.3
Additions to Carbonyls
119
7.3.1
1,2-Additions
119
7.3.2
1,4-Additions
121
7.3.3
Addition-Elimination Reactions
123
7.4
Summary
125
Problems
126
CONTEHTS
ІХ
8.
Moving Forward
135
8.1
Functional Group Manipulations
135
8.2
Name Reactions
139
8.3
Reagents
143
8.4
Final Comments
144
Problems
146
Appendix
1. pÄa
Values of Protons Associated with Common
Functional Groups
155
Appendix
2.
Answers and Explanations to Problems
159
Chapter
1
Solutions
159
Chapter
2
Solutions
173
Chapter
3
Solutions
191
Chapter
4
Solutions
205
Chapter
5
Solutions
223
Chapter
6
Solutions
233
Chapter
7
Solutions
243
Chapter
8
Solutions
261
Appendix
3.
Student Reaction Glossary
283
Index
287
Periodic Table of the Elements
301
|
| adam_txt |
Contents
PREFACE
xi
ACKNOWLEDGMENTS
xiii
ABOUT THE AUTHOR
xv
1.
Introduction
1
1.1
Definition of Arrow Pushing
1
1.2
Functional Groups
5
1.3
Nucleophiles and Leaving Groups
8
1.4
Summary
8
Problems
10
2.
Acids
19
2.1
What are Acids?
19
2.2
What is Resonance?
20
2.3
How is Acidity Measured?
23
2.4
Relative Acidities
25
2.5
Inductive Effects
29
2.6
Inductive Effects and Relative Acidities
31
2.7
Relative Acidities of Hydrocarbons
33
2.8
Summary 34
Problems
35
VII
VIH
CONTENTS
3.
Bases and Nucleophiles
45
3.1
What are Bases?
45
3.2
What are Nucleophiles?
50
3.3
Leaving Groups
54
3.4
Summary
55
Problems
56
4.
SN2 Substitution Reactions
65
4.1
What is an SN2 Reaction?
65
4.2
What are Leaving Groups?
67
4.3
Where Can SN2 Reactions Occur?
68
4.4
SN2' Reactions
71
4.5
Summary
73
Problems
74
5.
SN1 Substitution Reactions
83
5.1
What is an SN1 Reaction?
83
5.2
How are SN1 Reactions Initiated
84
5.3
The Carbocation
86
5.3.1
Molecular Structure and
Orbitals 86
5.3.2
Stability of Carbocations
90
5.4
Carbocation Rearrangements
92
5.4.1
1,2-Hydride Shifts
92
5.4.2 1,2-
Alkyl
Shifts
93
5.4.3
Preventing Side Reactions
95
5.5
Summary
96
Problems
97
6.
Elimination Reactions
101
6.1
El Eliminations
101
6.2
E2 Eliminations
104
6.3
How Do Elimination Reactions Work?
105
6.4
Summary
108
Problems
109
7.
Addition Reactions
115
7.1
Addition of Halogens to Double Bonds
115
7.2
Markovnikov's Rule
117
7.3
Additions to Carbonyls
119
7.3.1
1,2-Additions
119
7.3.2
1,4-Additions
121
7.3.3
Addition-Elimination Reactions
123
7.4
Summary
125
Problems
126
CONTEHTS
ІХ
8.
Moving Forward
135
8.1
Functional Group Manipulations
135
8.2
Name Reactions
139
8.3
Reagents
143
8.4
Final Comments
144
Problems
146
Appendix
1. pÄa
Values of Protons Associated with Common
Functional Groups
155
Appendix
2.
Answers and Explanations to Problems
159
Chapter
1
Solutions
159
Chapter
2
Solutions
173
Chapter
3
Solutions
191
Chapter
4
Solutions
205
Chapter
5
Solutions
223
Chapter
6
Solutions
233
Chapter
7
Solutions
243
Chapter
8
Solutions
261
Appendix
3.
Student Reaction Glossary
283
Index
287
Periodic Table of the Elements
301 |
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| isbn | 9780470171103 |
| language | English |
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| spelling | Levy, Daniel E. Verfasser aut Arrow pushing in organic chemistry an easy approach to understanding reaction mechanisms Daniel E. Levy Hoboken, N.J. Wiley 2008 XV, 301 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Includes index. Chemistry, Organic Textbooks Reaction mechanisms (Chemistry) Textbooks Reaktionsmechanismus (DE-588)4177123-0 gnd rswk-swf Organische Chemie (DE-588)4043793-0 gnd rswk-swf Chemische Reaktion (DE-588)4009853-9 gnd rswk-swf Organische Chemie (DE-588)4043793-0 s Chemische Reaktion (DE-588)4009853-9 s Reaktionsmechanismus (DE-588)4177123-0 s 1\p DE-604 Digitalisierung UB Bayreuth application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016775823&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis 1\p cgwrk 20201028 DE-101 https://d-nb.info/provenance/plan#cgwrk |
| spellingShingle | Levy, Daniel E. Arrow pushing in organic chemistry an easy approach to understanding reaction mechanisms Chemistry, Organic Textbooks Reaction mechanisms (Chemistry) Textbooks Reaktionsmechanismus (DE-588)4177123-0 gnd Organische Chemie (DE-588)4043793-0 gnd Chemische Reaktion (DE-588)4009853-9 gnd |
| subject_GND | (DE-588)4177123-0 (DE-588)4043793-0 (DE-588)4009853-9 |
| title | Arrow pushing in organic chemistry an easy approach to understanding reaction mechanisms |
| title_auth | Arrow pushing in organic chemistry an easy approach to understanding reaction mechanisms |
| title_exact_search | Arrow pushing in organic chemistry an easy approach to understanding reaction mechanisms |
| title_exact_search_txtP | Arrow pushing in organic chemistry an easy approach to understanding reaction mechanisms |
| title_full | Arrow pushing in organic chemistry an easy approach to understanding reaction mechanisms Daniel E. Levy |
| title_fullStr | Arrow pushing in organic chemistry an easy approach to understanding reaction mechanisms Daniel E. Levy |
| title_full_unstemmed | Arrow pushing in organic chemistry an easy approach to understanding reaction mechanisms Daniel E. Levy |
| title_short | Arrow pushing in organic chemistry |
| title_sort | arrow pushing in organic chemistry an easy approach to understanding reaction mechanisms |
| title_sub | an easy approach to understanding reaction mechanisms |
| topic | Chemistry, Organic Textbooks Reaction mechanisms (Chemistry) Textbooks Reaktionsmechanismus (DE-588)4177123-0 gnd Organische Chemie (DE-588)4043793-0 gnd Chemische Reaktion (DE-588)4009853-9 gnd |
| topic_facet | Chemistry, Organic Textbooks Reaction mechanisms (Chemistry) Textbooks Reaktionsmechanismus Organische Chemie Chemische Reaktion |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016775823&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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