This concise and accessible textbook provides notes for students studying chemistry and related courses at undergraduate level, covering core organic chemistry in a format ideal for learning and rapid revision. The material, with an emphasis on pictorial presentation, is organised to provide an overview of the essentials of functional group chemistry and reactivity, leading the student to a solid understanding of the basics of organic chemistry.
This revised and updated second edition of Keynotes in Organic Chemistry includes:
new margin notes to emphasise links between different topics,
colour diagrams to clarify aspects of reaction mechanisms and illustrate key points, and
a new keyword glossary.
In addition, the structured presentation provides an invaluable framework to facilitate the rapid learning, understanding and recall of critical concepts, facts and definitions. Worked examples and questions are included at the end of each chapter to test the reader's understanding.
Reviews of the First Edition
" …this text provides an outline of what should be known and understood, including fundamental concepts and mechanisms." Journal of Chemical Education, 2004
" Despite the book's small size, each chapter is thorough, with coverage of all important reactions found at first-year level... ideal for the first-year student wishing to revise… and priced and designed appropriately." The Times Higher Education Supplement, 2004
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Yes, you can access Keynotes in Organic Chemistry by Andrew F. Parsons in PDF and/or ePUB format, as well as other popular books in Ciencias físicas & Química orgánica. We have over one million books available in our catalogue for you to explore.
Key point. Organic chemistry is the study of carbon compounds. Ionic bonds involve elements gaining or losing electrons but the carbon atom is able to form four covalent bonds by sharing the four electrons in its outer shell. Single (C–C), double (C=C) or triple bonds (C
C) to carbon are possible. When carbon is bonded to a different element, the electrons are not shared equally, as electronegative atoms (or groups) attract the electron density whereas electropositive atoms (or groups) repel the electron density. An understanding of the electron-withdrawing or -donating ability of atoms, or a group of atoms, can be used to predict whether an organic compound is a good acid or base.
1.1 Ionic versus Covalent Bonds
Ionic bonds are formed between molecules with opposite charges. The negatively charged anion will electrostatically attract the positively charged cation. This is present in (inorganic) salts.
Covalent bonds are formed when a pair of electrons is shared between two atoms. A single line represents the two-electron bond.
Coordinate (or dative) bonds are formed when a pair of electrons is shared between two atoms. One atom donates both electrons and a single line or an arrow represents the two-electron bond.
The cyclic ether is tetrahydrofuran (THF) and BH3is called borane ( Section 6.2.2.5)
Hydrogen bonds are formed when the partially positive (δ+) hydrogen of one molecule interacts with the partially negative (δ−) heteroatom (e.g. oxygen or nitrogen) of another molecule.
Intramolecular hydrogen bonding in carbonyl compounds is discussed in Section 8.4.1
1.2 The Octet Rule
To form organic compounds, the carbon atom shares electrons to give a stable ‘full shell’ electron configuration of eight valence electrons.
Methane is the smallest alkane – alkanes are a family of compounds that contain only C and H atoms linked by single bonds (Section 2.4)
Drawing organic compounds using full structural formulae and other conventions is discussed in Section 2.5
A single bond contains two electrons, a double bond contains four electrons and a triple bond contains six electrons. A lone (or non-bonding) pair of electrons is represented by two dots (• •).
1.3 Formal Charge
Formal positive or negative charges are assigned to atoms, which have an apparent ‘abnormal’ number of bonds.
Nitric acid is used in synthesis to nitrate aromatic compounds such as benzene (Section 7.2.2)
Carbon forms four covalent bonds. When only three covalent bonds are present, the carbon atom can have either a formal negative charge or a formal positive charge.
The stability of carbocations and carbanions is discussed in Section 4.3
Carbanions –three covalent bonds to carbon and a formal negative charge.
Carbanions are formed on deprotonation of organic compounds. Deprotonation of a carbonyl compound, at the α-position, forms a carbanion called an enolate ion (Section 8.4.3)
Carbocations –three covalent bonds to carbon and a formal positive charge.
Carbocations are intermediates in a number of reactions, including S N1 reactions (Section 5.3.1.2)
1.4 Sigma (σ–) and pi (π–) Bonds
The electrons shared in a covalent bond result from overlap of atomic orbitals to give a new molecular orbital. Electrons in 1s and 2s orbitals combine to give sigma (σ–) bonds.
Molecular orbitals and chemical reactio...
Table of contents
Cover
Title Page
Copyright
Preface
Chapter 1: Structure and Bonding
Chapter 2: Functional Groups, Nomenclature and Drawing Organic Compounds
Chapter 3: Stereochemistry
Chapter 4: Reactivity and Mechanism
Chapter 5: Halogenoalkanes
Chapter 6: Alkenes and Alkynes
Chapter 7: Benzenes
Chapter 8: Carbonyl Compounds: Aldehydes and Ketones
Chapter 9: Carbonyl Compounds: Carboxylic Acids and Derivatives
Chapter 10: Spectroscopy
Chapter 11: Natural Products and Synthetic Polymers
Appendix 1: Bond Dissociation Enthalpies
Appendix 2: Bond Lengths
Appendix 3: Approximate pKa Values (Relative to Water)
