Introduction to Strategies for Organic Synthesis

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Laurie S. Starkey
John Wiley & Sons, Feb 21, 2012 - Science - 340 pages
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The stepping-stone text for students with a preliminary knowledge of organic chemistry looking to move into organic synthesis research and graduate-level coursework

Organic synthesis is an advanced but important field of organic chemistry, however resources for advanced undergraduates and graduate students moving from introductory organic chemistry courses to organic synthesis research are scarce. Introduction to Strategies for Organic Synthesis is designed to fill this void, teaching practical skills for making logical retrosynthetic disconnections, while reviewing basic organic transformations, reactions, and reactivities.

Divided into seven parts that include sections on Retrosynthesis and Protective Groups; Overview of Organic Transformations; Synthesis of Monofunctional Target Molecules; Synthesis of Target Molecules with Two Functional Groups; Synthesis of Aromatic Target Molecules; Synthesis of Compounds Containing Rings; and Predicting and Controlling Stereochemistry, the book covers everything students need to successfully perform retrosynthetic analyses of target molecule synthesis.

Starting with a review of functional group transformations, reagents, and reaction mechanisms, the book demonstrates how to plan a synthesis, explaining functional group analysis and strategic disconnections. Incorporating a review of the organic reactions covered, it also demonstrates each reaction from a synthetic chemist's point of view, to provide students with a clearer understanding of how retrosynthetic disconnections are made.

Including detailed solutions to over 300 problems, worked-through examples and end-of-chapter comprehension problems, Introduction to Strategies for Organic Synthesis serves as a stepping stone for students with an introductory knowledge of organic chemistry looking to progress to more advanced synthetic concepts and methodologies.

  

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Contents

Protective Groups
19
Common Electrophiles
26
xvii
41
1 Synthesis of Alcohols ROH
47
4
58
2 Synthesis of Alkyl RX and Aryl Halides ArX
61
3 Synthesis of Ethers ROR
67
5
68
Umpolung Polarity
165
Problems Target Molecules with Two Functional Groups
177
1 Electrophilic Aromatic Substitution
183
2 Synthesis of Aromatic TMs via Diazonium Salts
195
Problems Aromatic TMs
203
1 Synthesis of Cyclopropanes
209
3 Synthesis of FiveMembered Rings Radical
215
Problems Cyclic TMs
229

4 Synthesis of Thiols RSH and Thioethers RSR
73
5 Synthesis of Amines RNH2 and Anilines
77
Amine TM
83
Alkene TM
90
Alkyne TM
95
8
97
Retrosynthesis of Alkanes
101
11
103
Synthesis of AldehydesKetones via Acyl
107
10 Synthesis of Carboxylic Acids RCO2H
115
11 Synthesis of Carboxylic Acid Derivatives
121
Problems Monofunctional Target Molecules 1FG TMs
135
Synthesis of Target Molecules with Two Functional
139
Synthesis of αβUnsaturated Esters Using
149
The Michael Reaction
157
1 Reactions That Form Racemates
235
Backside Attack
241
4 Additions to Alkenes and Alkynes
245
Aldol Stereochemistry
253
Problems Stereochemistry
263
12
266
Nucleophiles Electrophiles and Redox
270
14
284
Difunctional Target Molecules 2FG TMs
286
Aromatic TMs
303
Stereochemistry
320
15
331
21
337
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About the author (2012)

Laurie S. Starkey, PHD, is a Full Professor of Chemistry at California State Polytechnic University, Pomona, where she has been teaching organic chemistry and organic synthesis since 1996. Dr. Starkey earned the College of Science's Distinguished Teaching Award in 2000 and the Provost's Award in Teaching Excellence at Cal Poly Pomona in 2013. Her research interests lie in the area of chemical education, including the development and assessment of online learning tools and the creation of educational videos for YouTube and Educator.com.

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