This book explains the modern theoretical concepts of organic chemistry to the extent needed for carrying out synthesis. A more detailed exposition of theoretical aspects, especially those involving the reaction mechanisms, is given in textbooks of organic chemistry.

This textbook presents a large number of syntheses. The greatest attention is devoted to laboratory operations which are of practical and methodological importance. If need be, a laboratory operation in a given subject can be replaced by a similar one in the students’ future speciality. In addition, when there is a large number of syntheses, the instructor can select those needed for review problems to see how well the students have learned their material.

Certain guides to organic synthesis were used when the textbook was being written.

This edition of the textbook has new material on the mechanism of individual reactions and a chapter on the identification of organic compounds.

Translated from the Russian by Nicholas Bobrov

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CONTENTS
Preface
Part I — METHODS USED IN ORGANIC SYNTHESIS
Chapter 1 — WORK AND SAFETY RULES
1.1. Principal Laboratory Operations
Assembly
Cleaning and Drying Laboratory Equipment
Literature, Notebooks and Reports
1.2. Safety Rules in the Organic Synthesis Laboratory
Precautions and First Aid in Case of Accidents
Work with Poisons and Caustics
Work with Highly Flammable Substances and Explosives
Rules of Handling Glassware
First Aid in Case of Burns, Poisonings and Other Accidents
Local Fires and Burning Laboratory Equipment
Chapter 2 — PRINCIPAL LABORATORY OPERATIONS
2.1. Heating
2.2. Cooling
2.3. Measuring and Controlling the Temperature
2.4. Grinding and Stirring
2.5. Dissolution and Properties of Some Organic Solvents
Ethyl Alcohol
Methyl Alcohol
Ether
Petroleum Ether
Acetone
2.6. Drying and Principal Drying Agents
Drying Gases
Drying Organic Liquids
Drying Solids
Principal Drying Agents
2.7. Filtration
Filtration at Atmospheric Pressure
Suction Filtration
Chapter 3 — METHODS OF PURIFYING ORGANIC SUBSTANCES
3.1. Crystallisation
Solvent Selection
Recrystallisation Procedure
Formation of Crystals
3.2. Sublimation
3.3. Extraction
3.4. Distillation
Simple Distillation at Atmospheric Pressure
Steam Distillation
Vacuum Distillation (at Reduced Pressure)
Fractional Distillation
Rectification
3.5. Chromatography
Adsorption Chromatography (Column Chromatography)
Partition Chromatography
Paper Chromatography
Ion Exchange Chromatography
Chapter 4 — DETERMINATION OF THE PRINCIPAL CONSTANTS OF ORGANIC COMPOUNDS
4.1. Melting Point
4.2. Boiling Point
4.3. Specific Gravity
4.4. Refractive Index
4.5. Molecular Weight
Chapter 5 — WORK WITH COMPRESSED AND LIQUEFIED GASES
5.1. Gas Cylinders and How to Use Them
5.2. Dosing Gases
5.3. Purification of Gases and Their Introduction into an Apparatus
5.4. Safety Rules in Handling Gas Cylinders
Chapter 6 — QUANTITATIVE ELEMENTAL ANALYSIS OF ORGANIC SUBSTANCES
6.1. Semimicrodetermination of Carbon and Hydrogen
Assembly
Analysis
6.2. Semimicrodetermination of Nitrogen (According to Dumas)
Assembly
Analysis
6.3. Microdetermination of Carbon and Hydrogen
Assembly
Analysis
Part II — SYNTHESES OF ORGANIC SUBSTANCES
Chapter 7 — HALOGENATION REACTIONS
7.1. Replacement of the Hydroxyl Group of Alcohols by a Halogen
7.2. Replacement of the Hydroxyl Group of Acids by a Halogen
7.3. Halogen Addition to a Multiple Bond
7.4. Direct Replacement of Hydrogen by a Halogen
7.5. Syntheses
Ethyl Bromide
Acetylene and Ethyl Bromide
Ethyl Iodide
Butyl Bromide
Acetyl Chloride
Benzoyl Chloride
1,2-Dibromoethane
Bromobenzene
α-Bromonaphthalene
p-Bromoanisole
Chapter 8 — ALKYLATION REACTIONS
8.1. Alkylation of Aromatic Compounds by Alcohols in the Presence of Sulphuric Acid
8.2. Preparation of Ethers
8.3. Syntheses
sec-Butylbenzene
Dibutyl Ether
Isoamyl Ether
Diphenyl Ether
Phenetole
β-Naphthyl Ethyl Ether (Nerolin, Bromelia)
Anisole
Chapter 9 — ACYLATION REACTIONS
9.1. Acylation of Alcohols and Amines by Carboxylic Acids
9.2. Acylation of Alcohols, Phenols and Amines by Acyl Chlorides
9.3. Acylation of Amines by Acid Anhydrides
9.4. Syntheses
Ethyl Acetate
Isoamyl Acetate
Ethyl Chloroacetate
Diethyl Oxalate (Oxalic Ester)
Ethyl Benzoate
Benzanilide
Aspirin (Acetylsalicylic Acid)
β-Naphthyl Acetate
Acetanilide
Chapter 10 — FRIEDEL-CRAFTS REACTIONS
10.1. Alkylation of Aromatic Compounds
10.2. Acylation of Aromatic Compounds
10.3. Syntheses
Isopropylbenzene
Diphenylmethane
Acetophenone
Benzophenone
Chapter 11 — OXIDATION REACTIONS
11.1. Oxidation at the Double Bond
11.2. Oxidation of Primary and Secondary Alcohols to Aldehydes or Ketones
11.3. Oxidation of Aldehydes and Ketones to Acids
11.4. Oxidation of Methyl and Methylene Groups
11.5. Preparation of Quinones by Oxidation
11.6. Syntheses
Acetaldehyde
Propionaldehyde
Isovaleraldehyde
Benzophenone
Isobutyric Acid
Valeric Acid
Benzoic Acid
Benzoquinone
Anthraquinone
Chapter 12 — NITRATION REACTIONS
12.1. Nitration of Hydrocarbons of the Fatty Series
12.2. Nitration of Hydrocarbons of the Aromatic Series
12.3. Syntheses
Nitromethane
Nitrobenzene
o-,p-Nitrotoluene
o-,p-Nitrophenol
α-Nitronaphthalene
Chapter 13 — AMINATION REACTIONS
13.1. Preparation of Amines of the Fatty Series
13.2. Preparation of Amines of the Aromatic Series
13.3. Syntheses
Methylamine
Aniline
o-,p-Toluidine
α-Naphthylamine
Preparation of α-Naphthylamine Hydrochloride
Chapter 14 — SULPHONATION REACTIONS
14.1. Sulphonation of Aromatic Compounds
14.2. Syntheses
β-Naphthalenesulphonic Acid (Sodium Salt)
Benzenesulphonic Acid (Sodium Salt)
p-Toluenesulphonic Acid
Sulphanilic Acid
Chapter 15 — DIAZOTIZATION AND AZO COUPLING REACTIONS
15.1. Diazonium Salt Reactions with Loss of Nitrogen
15.2. Diazonium Salt Reactions without Loss of Nitrogen
15.3. Syntheses
Phenol
Iodobenzene
Helianthin
β-Naphthol Orange
Chapter 16 — GRIGNARD REACTIONS
16.1. Preparation of Hydrocarbons
Quantitative Determination of Active Hydrogen by the Chugaev-Tserevitinov Method
16.2. Preparation of Carboxylic Acids
16.3. Preparation of Alcohols
16.4. Syntheses
Phenylacetic Acid
Triphenylcarbinol
Diphenylcarbinol (Benzhydrol)
Chapter 17 — CANNIZZARO REACTIONS
17.1. Synthesis of Benzoic Acid and Benzyl Alcohol
Chapter 18 — CLAISEN REACTIONS
18.1. Syntheses
Ethyl Acetoacetate
Benzoylacetone
Chapter 19 — POLYMERIZATION AND POLYCONDENSATION REACTIONS
19.1. Polymerization
19.2. Polycondensation (Condensation Polymerization)
19.3. Syntheses
Paraldehyde
Polystyrene
Polymethyl Methacrylate
Copolymer of Styrene with Methyl Methacrylate
Methyl Methacrylate (from Methyl Methacrylate)
Glyptal Resin
Phenol-Formaldehyde Resin
Chapter 20 — IDENTIFICATION
20.1. Preliminary Tests
20.2. Qualitative Reactions
20.3. Preparation of Derivatives
RECOMMENDED LITERATURE
SUPPLEMENTS
Drying Agents for Organic Compounds
Steam Pressure at Different Temperatures
Pressure of Liquefied Gases in Cylinders
Colour Code of Compressed Gas Cylinders
Density of Sulphuric Acid Solutions (20°C)
Density of Hydrochloric Acid Solutions (20°C)
Density of Nitric Acid Solutions (20°C)
Density of Sodium Hydroxide Solutions (20°C)
Density of Potassium Hydroxide Solutions (20°C)
Physical Properties of Alcohols and Their Derivatives
Physical Properties of Phenols and Their Derivatives
Physical Properties of Aldehydes and Their Derivatives
Physical Properties of Ketones and Their Derivatives
Physical Properties of Carboxylic Acids and Their Derivatives
Physical Properties of Primary and Secondary Amines and Their Derivatives (Acetamides)
Physical Properties of Acid Halides and Their Derivatives (Anilides)