Introduction to the strategies of organic synthesis

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.

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 ß-HYDROXY CARBONYLS AND ,ß-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