PREFACE PHILOSOPHY to grasp the material most readily. Students retain the material best, however, if they understand how organic From its first edition through this, its fourth, Organic reactions take place. Thus, reaction mechanisms are Chemistry has been designed to meet the needs of the stressed early and often, but within a functional group framework. a closer examination of the chapter titles chemistry course. It has evolved as those needs have reveals the close link between a functional group class changed, but its philosophy remains the same. The over arching theme is that organic chemistry is not only an ( Chapter 20, Carboxylic Acid Derivatives)and a reaction interesting subject, but also a logical one. It is logical ype(Nucleophilic Acyl Substitution), for example. It is very satisfying to see students who entered the course because its topics can be connected in a steady pro- believing they needed to memorize everything progress ssion from simple to complex. Our approach has been to reveal the logic of organic chemistry by being to the point of thinking and reasoning mechanistically elective in the topics we cover, as well as thorough and Some of the important stages in this approach are patient in developing them. eaching at all levels is un especially in applying powerful tools that exploit the graphics capability of personal computers. Organic halides. Not only is this a useful functional-group chemistry has always been the most graphical of the transformation, but its first step proceeds by the chemical sciences and is well positioned to benefit sig simplest mechanism of all--proton transfer. The nificantly from these tools. Consistent with our philoso- overall mechanism provides for an early rein- phy, this edition uses computer graphics to enhance the forcement of acid-base chemistry and an early core material. to make it more visual. and more under- introduction to carbocations and nucleophilic sub- standable, but in a way that increases neither the amount station of material nor its level Chapter 5 continues the chemistry of alcohols and alkyl halides by showing how they can be used to ORGANIZATION prepare alkenes by elimination reactions. Here, the students see a second example of the formation of The central message of chemistry is that the properties carbocation intermediates from alcohols, but in of a substance come from its structure. what is less this case, the carbocation travels a different path obvIous. bu very powerful, is the corollary. Someone way to a different destination with training in chemistry can look at the structure of a substance and tell you a lot about its properties. Organic The alkenes prepared in Chapter 5 are studied chemistry has always been, and continues to be, the again in Chapter 6, this time with an eye toward branch of chemistry that best connects structure with their own chemical reactivity. What the students properties. This text has a strong bias toward structure, learned about carbocations in Chapters 4 and 5 and this edition benefits from the availability of versa- serves them well in understanding the mechanisms tile new tools to help us understand that structure of the reactions of alkenes in Chapter 6 The text is organized to flow logically and step by Likewise, the mechanism of nucleophilic addition step from structure to properties and back again. As the the carbonyl group of aldehydes and ketones list of chapter titles reveals, the organization is accord scribed in Chapter 17 sets the stage for aldol con- ing to functional groups--structural units within a mol- densation in Chapter 18, esterification of carboxylic ecule most responsible for a particular property- acids in Chapter 19, nucleophilic acyl substitution in because that is the approach that permits most students Chapter 20, and ester condensation in Chapter 21 Forward Main Menu TOC Study Guide Toc Student OLCMHHE WebsitePREFACE xxv PHILOSOPHY From its first edition through this, its fourth, Organic Chemistry has been designed to meet the needs of the “mainstream,” two-semester, undergraduate organic chemistry course. It has evolved as those needs have changed, but its philosophy remains the same. The over￾arching theme is that organic chemistry is not only an interesting subject, but also a logical one. It is logical because its topics can be connected in a steady pro￾gression from simple to complex. Our approach has been to reveal the logic of organic chemistry by being selective in the topics we cover, as well as thorough and patient in developing them. Teaching at all levels is undergoing rapid change, especially in applying powerful tools that exploit the graphics capability of personal computers. Organic chemistry has always been the most graphical of the chemical sciences and is well positioned to benefit sig￾nificantly from these tools. Consistent with our philoso￾phy, this edition uses computer graphics to enhance the core material, to make it more visual, and more under￾standable, but in a way that increases neither the amount of material nor its level. ORGANIZATION The central message of chemistry is that the properties of a substance come from its structure. What is less obvious, but very powerful, is the corollary. Someone with training in chemistry can look at the structure of a substance and tell you a lot about its properties. Organic chemistry has always been, and continues to be, the branch of chemistry that best connects structure with properties. This text has a strong bias toward structure, and this edition benefits from the availability of versa￾tile new tools to help us understand that structure. The text is organized to flow logically and step by step from structure to properties and back again. As the list of chapter titles reveals, the organization is accord￾ing to functional groups—structural units within a mol￾ecule most responsible for a particular property— because that is the approach that permits most students to grasp the material most readily. Students retain the material best, however, if they understand how organic reactions take place. Thus, reaction mechanisms are stressed early and often, but within a functional group framework. A closer examination of the chapter titles reveals the close link between a functional group class (Chapter 20, Carboxylic Acid Derivatives) and a reaction type (Nucleophilic Acyl Substitution), for example. It is very satisfying to see students who entered the course believing they needed to memorize everything progress to the point of thinking and reasoning mechanistically. Some of the important stages in this approach are as follows: • The first mechanism the students encounter (Chap￾ter 4) describes the conversion of alcohols to alkyl halides. Not only is this a useful functional-group transformation, but its first step proceeds by the simplest mechanism of all—proton transfer. The overall mechanism provides for an early rein￾forcement of acid-base chemistry and an early introduction to carbocations and nucleophilic sub￾stitution. • Chapter 5 continues the chemistry of alcohols and alkyl halides by showing how they can be used to prepare alkenes by elimination reactions. Here, the students see a second example of the formation of carbocation intermediates from alcohols, but in this case, the carbocation travels a different path￾way to a different destination. • The alkenes prepared in Chapter 5 are studied again in Chapter 6, this time with an eye toward their own chemical reactivity. What the students learned about carbocations in Chapters 4 and 5 serves them well in understanding the mechanisms of the reactions of alkenes in Chapter 6. • Likewise, the mechanism of nucleophilic addition to the carbonyl group of aldehydes and ketones described in Chapter 17 sets the stage for aldol con￾densation in Chapter 18, esterification of carboxylic acids in Chapter 19, nucleophilic acyl substitution in Chapter 20, and ester condensation in Chapter 21