Solomons/Fryhle Organic Chemistry 8/e
Annotated Table of Contents

1.	Carbon Compounds and Chemical Bonds

Additional coverage of the rules for writing proper resonance structures and evaluating their importance in overall hybrid

New computer molecular modeling problems (in all chapters) – reinforces concepts with models viewed using Chem3D web plug-in

2.	Representative Carbon Compounds:  Functional Groups, Intermolecular Forces, and Infrared (IR) Spectroscopy

Chapter opening vignette on molecular machines and biomimetic materials shows the importance of functional groups, polarity and intermolecular forces in biomedical, computing, and materials science applications.

3.	An Introduction to Organic Reactions:  Acids and Bases

Calculated computer models depicting molecular orbitals in a Lewis acid and base example can be viewed from the CD/Web using the Chem3D plug-in

Problems using electrostatic potential maps to illustrate charge distribution help students understand the significance of resonance hybrids and charge delocalization.

4.	Alkanes: Nomenclature, Conformational Analysis, and an Introduction to Synthesis

Incorporates the most recent IUPAC recommendations for nomenclature

Discussion of relative stability of ethane conformers has been updated to reflect recent research on molecular orbital effects, hyperconjugation, and conformational analysis.

5.	Stereochemistry:  Chiral Molecules

Section on origin of optical activity has been substantially revised to provide an enhanced explanation  for they physical basis of the rotation of plane-polarized light by chiral molecules.

The stereochemistry of BINAP, a compound capable of conformational stereosomerims, is highlighted in this section for its important use as a ligand for enantioselective catalysis.

6.	Ionic Reactions – Nucleophilic Substitution and Elimination Reactions of Alkyl Halides

Free energy versus Reaction Progress plots have been added to show relative changes in energy of reactants and intermediates in the “Mechanism for the SN1 Reaction” box.

New SN1, SN2, and E2 Mechanism Summary and Review Tools added.

7.	Alkenes and Alkynes:  Properties and Synthesis.  Elimination Reactions of Alkyl Halides

Now discusses homogeneous as well as  heterogenous hydrogenation catalysis, because of the importance of homogenous catalysis in stereoselective reactions. 

8.	Alkenes and Alkynes II.  Addition Reactions

Section on Markovnik Additions moved to this chapter to introduce synthesis of alcohols from alkenes by acid-catalyzed hydration, which is now compared directly with more common synthetic methods of oxymercuration-dumurcuration and hydroboration-oxidation.

Section on hydroboration substantially recast to highlight stereochemistry and regiochemistry of the hydroboration step.

Section on oxidation of alkenes provides an introduction to “green chemistry” by its coverage of catalytic methods of osmium hydroxylation.

9.	Nuclear Magnetic Resonance and Mass Spectrometry:  Tools for Structure Determination

Section on  mass spectrometry of biomolecules whets the appetite of interested students for more information on emerging applications of MS.

10.	Radical Reactions

New section describes role of nitric oxide as key chemical messenger in blood pressure regulation, the immune response, and smooth muscle relaxation.

Special Topic A:  Chain–Growth Polymers

11.	Alcohols and Ethers 

Section on synthesis of alcohols from alkenes has been abridged (details moved to Chapter 8)so it now serves a brief reminder of the methods for synthesizing alcohols from alkenes.

New “The Chemistry of … Environmentally-Friendly Alkene Oxidation Methods” discusses “green chemistry” methods of alkene oxidation by catalysts such as Jacobsen’s catalyst.

12.	Alcohols from Carbonyl Compounds.  Oxidatation-Reduction and Organometallic Compounds

New schematic showing some synthetic connections of alcohols and carbonyl compounds serves as summary and review tool for reactions discussed in chapter.

13.	Conjugated Unsaturated Systems

New “The Chemistry of … The Photochemistry of Vision” provides direct illustration of a key biological example of light absorption by a conjugated system.

14.	Aromatic Compounds

Chapter opening vignette on “green chemistry” describes progress in synthetic methods that are environmentally friendly.

Six pi molecular orbitals of benzene are represented by calculated molecular orbitals.  Throughout chapter orbital shapes have been updated with molecular orbital descriptions of aromatic molecules and ions as well.

15.	Reactions of Aromatic Compounds

New synthetic connection schematic shows reactions from this and other chapters that  link benzene and aryl derivatives.

16.	Aldehydes and Ketones I.  Nucleophilic Addition to the Carbonyl Group

Section on addition of derivatives of primary and secondary amines has been reorganized to highlight the mechanistic differences caused by attacking nitrogen having eith one hydrogen or two hydrogen atoms initially bonded to it when it reacts with aldehyde or ketone.

New section on oxidation of aldehydes and ketones includes “green chemistry” version of Baeyer-Villiger reaction.

17.	Aldehydes and Ketones II.  Aldol Reactions

New mechanism summary and review tool summarized nucleophilic reactions of enolates and other carbon groups that become nucleophilic by loss of an acidic hydrogen.

18.	Carboxylic Acids and their Derivatives. Nucleophilic Addition-Elimination at the Acyl Carbon

Includes new carbonyl IR absorption chart

        Special Topic B
 
Topics in “green chemistry” relating to polymers are discussed in two new boxes.

19.	Synthesis and Reactions of -Dicarbonyl Compounds: More Chemistry of Enolate Ions

Key sections about -dicarbonyl compounds reflect the common themes among them and emphasize aspects of their synthetic utility

Special Topic C: Thiols, Sulfur Ylides, and Disulfides

Special Topic D:  Thiol Esters and Lipid Biosynthesis

20.	Amines

Basicity of heterocyclic amines (formerly a special topic) is now included in this chapter.

Special Topic E:  Alkaloids

21.	Phenols and Aryl Halides:  Nucleophilic Aromatic Substitution

New “The Chemistry of …” box  describes the biochemical oxidation of hydroquinones and resulting boiling hot spray of quinines used by the bombardier beetle to ward off predators. 

       Special Topic F:  Electrocyclic and Cycloaddition Reactions

       Special Topic G:  Transition Metal Organometallic Compounds

        Special Topic H:  Organic Halides and Organometallic Compounds in the Environment

22.	Carbohydrates

New “The Chemistry of …” box  explains a powerful method for solid-phase synthesis of complex oligosaccharides, highlighting new applications of solid-phase synthesis in carbohydrate chemistry.

23.	Lipids

New “The Chemistry of …” box discusses potential uses of self-assembled monolayers and Langmuir-Blodgett films in biomedical and nanotechnology applications.

Another new “The Chemistry of …” box explains the use of molecular capsules, made of phospholipid bilayers coated with synthetic polymer, that can be used to deliver drug molecules such as the anticancer drug doxorubicin.

24.	Amino Acids and Proteins

Section on laboratory synthesis of -amino acids has been updated to include enantioselective methods for synthesis of amino acids based on Nobel Prize-winning chemistry.

New section, introducing protemics, discusses the methods and tools for qualitative and quantitative analysis of all the proteins expressed by a cell.

25.	Nucleic Acids and Protein Synthesis    

Chapter has been updated to reflect completion of sequencing of the human genome.