Free download Reactions Rearrangements and Reagents by S N Sanyal

Authors of:  Reactions Rearrangements and Reagents by S N Sanyal

Somorendra Nath Sanyal

Table of Contents in Reactions Rearrangements and Reagents by S N Sanyal

1. Mechanism of Organic Reactions

– Types of Chemical Bonds  

Chemical bonds are the attractive forces that hold atoms together in compounds. These bonds form due to the interactions between the electrons of atoms, aiming to achieve a more stable electron configuration. There are several types of chemical bonds, each differing in how electrons are shared or transferred between atoms.

1. Ionic Bond: Ionic bonds occur when one atom transfers electrons to another, resulting in the formation of charged ions. Typically, this happens between a metal and a non-metal. The metal loses electrons to form a positively charged ion (cation), while the non-metal gains electrons to form a negatively charged ion (anion). The electrostatic attraction between these oppositely charged ions creates a strong ionic bond. An example of an ionic bond is the bond in sodium chloride (NaCl), where sodium donates an electron to chlorine.

2. Covalent Bond: In a covalent bond, electrons are shared between atoms rather than transferred. This type of bond commonly forms between non-metals. Depending on the number of shared electron pairs, covalent bonds can be single (one pair shared), double (two pairs shared), or triple (three pairs shared). Covalent bonds can be polar or nonpolar. In nonpolar covalent bonds, electrons are shared equally, as seen in molecules like hydrogen (H₂). In polar covalent bonds, electrons are shared unequally, leading to partial charges on the atoms, such as in water (H₂O).

3. Metallic Bond: Metallic bonds are formed in metals where atoms share a “sea of electrons.” These delocalized electrons are free to move throughout the metal lattice, giving metals their characteristic properties like electrical conductivity, malleability, and luster. The bond results from the attraction between the positively charged metal ions and the free-moving electrons.

4. Hydrogen Bond: Though weaker than ionic and covalent bonds, hydrogen bonds play a crucial role in the structure of biological molecules like DNA. This type of bond forms when a hydrogen atom, covalently bonded to a highly electronegative atom (like nitrogen or oxygen), experiences attraction to another electronegative atom nearby.

Each type of chemical bond contributes uniquely to the properties of substances, influencing their stability, reactivity, and physical characteristics. Understanding these bonds is crucial for explaining how molecules and compounds form and interact in various chemical reactions.

– Factors Influencing Reactivity  

– The Breaking and Making of Bonds  

– Energetics of Reactions  

– Classification of Organic Reactions  

2. Reactions and Rearrangements

– Acyloin Condensation  

– Aldol Condensation  

– Allylic Rearrangement  

– Arndt-Eistert Reaction  

– Baeyer-Villiger Rearrangement  

– Beckmann Rearrangement  

– Benzilic Acid Rearrangement  

– Birch Reduction  

– Cannizzaro Reaction  

– Claisen Condensation  

– Claisen Rearrangement  

– Claisen-Schmidt Reaction  

– Clemmensen Reduction  

– Curtius Reaction  

– Dieckmann Reaction  

– Diels-Alder Reaction  

– Dienone-Phenol Rearrangement  

– Favorskii Rearrangement  

– Friedel-Crafts Reaction  

– Fries Rearrangement  

– Gabriel Synthesis  

– Hell-Volhard-Zelinsky Reaction  

– Hofmann Rearrangement or Hofmann Bromamide Reaction  

– Houben-Hoesch Reaction  

– Knoevenagel Reaction  

– Mannich Reaction  

– Meerwein-Ponndorf-Verley Reduction  

– Michael Reaction  

– Oppenauer Oxidation  

– Perkin Reaction  

– Pinacol-Pinacolone Rearrangement  

– Reformatsky Reaction  

– Reimer-Tiemann Reaction  

– Sandmeyer Reaction  

– Schmidt Reaction  

– Sommelet Reaction  

– Stobbe Condensation  

– Stork Enamine Reaction  

– Ullmann Reaction  

– Vilsmeier-Haack Reaction  

– Wagner-Meerwein Rearrangement  

– Wittig Reaction  

– Wolff-Kishner Reduction  

– Wolff Rearrangement  

3. Important Reagents

– Anhydrous Aluminium Chloride  

– Aluminium Isopropoxide  

– Boron Trifluoride  

– N-Bromosuccinimide (NBS)  

– Diazomethane  

– Dicyclohexylcarbodiimide  

– Fenton’s Reagent  

– Hydrogen Peroxide  

– Lead Tetraacetate  

– Lithium Aluminium Hydride  

– Osmium Tetroxide  

– Perbenzoic Acid  

– Periodic Acid  

– Raney Nickel  

– Selenium Dioxide  

– Sodium Amide  

– Sodium Borohydride  

– Wilkinson’s Catalyst  

– Ziegler-Natta Catalysts  

Appendix A: Some More Reactions and Rearrangements

– Exercises for Chapter 1  

– Exercises for Chapter 2  

– Exercises for Chapter 3  

– Simple Problems and Solutions  

Chapter 1: Mechanism of Organic Reactions

Organic reactions involve the breaking and forming of covalent bonds, with chemists focusing not only on the outcome but also on the process. Understanding this mechanism allows chemists to design new molecules and predict products. Organic reactions typically proceed in steps, leading to a transformation of reactants into products, known as the reaction mechanism.

This mechanism is considered well-established if the intermediates of all steps can be isolated, though this is rarely possible. Several guiding principles help predict these steps, which include factors like reaction kinetics, isolation of intermediates, studies of similar substrates, isotopic labeling, trapping of free radicals, crossover experiments, and stereochemical considerations.

The study of organic reactions provides significant insights into theoretical organic chemistry. It helps predict reaction products from similar substrates, allowing for better control over reaction conditions and improving yields. This understanding has revolutionized organic chemistry, leading to advances in the synthesis of essential compounds, including drugs, vitamins, hormones, natural products, synthetic fibers, insecticides, fuels, and more.

In studying carbon compounds, it is essential to understand how carbon forms bonds with other atoms, which is foundational to the study of organic chemistry. Through this knowledge, chemists have developed critical tools to manipulate organic reactions and synthesize vital compounds.

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