Introduction to Strategies for Organic Synthesis (eBook)

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.

PART I. SYNTHETIC TOOLBOX 1: RETROSYNTHESIS AND PROTECTIVE GROUPS

1.1 RETROSYNTHETIC ANALYSIS

1.2 PROTECTIVE GROUPS

PART I PROBLEMS (PROTECTIVE GROUPS)

PART II SYNTHETIC TOOLBOX 2: OVERVIEW OF ORGANIC TRANSFORMATIONS

2.1 NUCLEOPHILES AND ELECTROPHILES

2.2 OXIDATION AND REDUCTION REACTIONS

PART II PROBLEMS (NUCLEOPHILES, ELECTROPHILES AND REDOX)

PART III. SYNTHESIS OF MONOFUNCTIONAL TARGET MOLECULES (1-FG TM'S)

3.1 SYNTHESIS OF ALCOHOLS (ROH)

3.2 SYNTHESIS OF ALKYL (RX) AND ARYL HALIDES (ArX)

3.3 SYNTHESIS OF ETHERS (ROR')

3.4 SYNTHESIS OF THIOLS (RSH) AND THIOETHERS (RSR')

3.5 SYNTHESIS OF AMINES (RNH2) AND ANILINES (ArNH2)

3.6 SYNTHESIS OF ALKENES (R2C=CR2)

3.7 SYNTHESIS OF ALKYNES (RC=CR')

3.8 SYNTHESIS OF ALKANES (RH)

3.9 SYNTHESIS OF ALDEHYDES AND KETONES (RCHO, R2C=O)

3.10 SYNTHESIS OF CARBOXYLIC ACIDS (RCO2H)

3.11 SYNTHESIS OF CARBOXYLIC ACID DERIVATIVES

PART III PROBLEMS (1-FG TM'S)

PART IV SYNTHESIS OF TARGET MOLECULES WITH TWO FUNCTIONAL GROUPS (2-FG TM'S)

4.1 SYNTHESIS OF beta-HYDROXY CARBONYLS AND alpha,beta-UNSATURATED CARBONYLS

4.2 MORE ENOLATE REACTIONS: SYNTHESIS OF 1,3-DICARBONYLS, 1,5-DICARBONYLS AND CYCLOHEXENONES

4.3 "ILLOGICAL" DISCONNECTIONS: UMPOLUNG (POLARITY REVERSAL)

PART IV PROBLEMS (2-FG TM'S)

PART V SYNTHESIS OF AROMATIC TARGET MOLECULES

5.1 ELECTROPHILIC AROMATIC SUBSTITUTION (ArH + E+ -> ArE)

5.2 SYNTHESIS OF AROMATIC TM'S VIA DIAZONIUM SALTS (ArN2+ + Nu -> ArNu)

5.3 NUCLEOPHILIC AROMATIC SUBSTITUTION (ArX + Nu: -> ArNu)

PART V PROBLEMS (AROMATIC TM'S)

PART VI SYNTHESIS OF COMPOUNDS CONTAINING RINGS

6.1 SYNTHESIS OF CYCLOPROPANES

6.2 SYNTHESIS OF CYCLOBUTANES

6.3 SYNTHESIS OF 5-MEMBERED RINGS (RADICAL CYCLIZATION REACTIONS)

6.4 SYNTHESIS OF 6-MEMBERED RINGS (DIELS-ALDER REACTION)

PART VI PROBLEMS (CYCLIC TM'S)

PART VII PREDICTING AND CONTROLLING STEREOCHEMISTRY

7.1 REACTIONS THAT FORM RACEMATES

7.2 SN2 MECHANISM: BACKSIDE ATTACK

7.3 ELIMINATION MECHANISMS

7.4 ADDITIONS TO ALKENES AND ALKYNES

7.5 ADDITIONS TO CARBONYLS

7.6 ADDITIONS TO ENOLATES: ALDOL STEREOCHEMISTRY

7.7 ENANTIOSELECTIVITY AND ASYMMETRIC SYNTHESES

PART VII PROBLEMS (STEREOCHEMISTRY)

SOLUTIONS TO PROBLEMS

"Finally, my overall impression of the book is that itwill serve well as a quick reference or starting point for anundergraduate researcher or new PhD student in organic synthesis.It is essentially a back-to-basics textbook and there may even besomething there for the odd academic who needs some inspirationwhen handed a new teaching assignment in an undergraduate subjectin organic synthesis." (Angewandte Chemie, 1September 2012)

"I will certainly be recommending it to my ownstudents." (ChemMedChem, 1 January 2013)

"Summing Up: Recommended. Lower-and upper-divisionundergraduates." (Choice, 1 November 2012)