What ts Organic Chemistry? 2 Where Do We Obtain Organic Compounds? How Do We Write Structural Organic Chemistry The bark of the Pacific yew contains paclitaxel, a substance that has effective in treating certain types of ovarian and breast cancer (see Chemical Connections 104). 10-1 What Is Organic Chemistry? Organic chemistry is the chemistry of the study Chapters 10-19 (organie will see that organic eo our foods, favo compounds of carbon. As you hemistry) and 20-31 (bioch npounds are ey and fragr metics; in our plastics, films, emistry), You ‘ywhere around us. They are i “si in our medicines, toiletries, and cos bers, and resins; and glues; and, of course, in our bod in our paints, varnishes, ies and the bodies of all other living organisms. Perhaps the most remarkable fe, ture of org: they involve the chemistry carbon nic compounds is that and only a few other elements ‘nitrogen, While the majority of organi® and just these three elements many als0 luorine, bromine, or iodine), and chiefly, hydrogen, oxygen, an¢ compounds contain carbon contain sulfur, a halogen (f chlorine, phosphoru: As of the writing of this text, there chemistry concentrat the ott are 8 on carbon, just on her 117 elements comes under the we see in Figure 10-1, carbon is f elements in the 118 known elements. Organi€ e of the 118. The chemistry field of inorganic chemistry. A? rth's crust, In watt being among the most abundant ea Se sas of elemental abundance, approx! mately 75% of the * crust is composed of just two elementa: exVEe Scanned with CamScannerScanned with CamScanner262] Chapter 10 Organic Chemisty > The vitamin C in an orange is identical to ite synthetic tablet form, Inorganic Compounds jerties of Organic and Table 10-1 A Comparison of Properties of Inorganic Compounds ceca it mrt covalent, ‘Most are solids with high melting secrlaree Ma opin solvents such as diethyl ether, solver Aqueous solutions do not conduct. Aqueous 7" ng ie eae os i ‘Very few burn. Seni | ee because they obey different natural all compounds, Of course, the entri I lavis. One set of natural laws applies tp they are largely true for the vast ies in Table 10-1 are generalizations, but majority of compounds of both types. 10-2 Where Do We Obtain Organic Compounds? Chemists obtain organic compounds in two Principal ways: isolation from nature and synthesis in the laboratory. A. Isolation from Nature s are “chemic: (flora) and ai bacteria—makes thousands synthesis. One way, then, to burify them from biological al factories.” Each terrestrial, marine, and Cathe ne eran crag eames of organic compounds by a proces called bio- Bet organic compounds is to extract, isolate, and Sources. In this book, w B. Synthesis in the Labor, atory Ever since Wohler synthesized o OF ote MAYS to synthesing the myCEBBIC chemists have sought to de- of those found in nature, become ‘me compounds or deve Ip thant Years, the methon de 80 sophisticated th ee £8 natucal organ oink 8 have matter how complicated, t at che, anic compounds, n0 supunds mado oe abn’ a0 pga OM Physical propertios to thane found in naeunee eetical in both chemical and inno way that aentt™*—assuming of course, that each Pea Was made by chrome CAB tell whe er a sample of any re ethanol made by itera hac etained from nature, bas sim cS cy Daying more mar AS ta tt BEC cane tilling wine. {Paying more money for vie aitere is no Fc, , for synthetic vitamin © bos tin C 9 ined from a mare aes therefore * Dense the aan [A Patural souree than cal in every way, 4 i a aaa Scanned with CamScanner Particular ¢ vequence, pty is? (263 mmm 1". COVVECTIONS 10 Taxol: A Story of Search and In the early 1960s, the National Cancer Institute under took 8 program to analyze samples of native plant ma- terials in the hope of discovering substances that would prove effective in the fight against cancer, Among the materials tested was an extract of the bark of the Pacific yew, Taxus brevifolia, a slow-growing tree found in the old-growth forests of the Pacific Northwest, This biologi cally active extract proved to be remarkably effective in treating certain types of ovarian and breast cancer, even in cases where other forms of chemotherapy failed. The structure of the cancer-fighting component of yew bark was determined in 1962, and the compound was named paclitaxel (Taxol Unfortunately, the bark of a single 100-year-old yew ‘tree yields only about 1 g of Taxol, not enough for effective treatment of even one cancer patient. Furthermore, iso- ating Taxol means stripping the bark from trees, which ills them. In 1994, chemists succeeded in synthesizing Taxol in the laboratory, but the cost of the synthetic drug ‘was far too high to be economical. Fortunately, an alter- native natural source of the drug was found. Researchers in France discovered that the needles of a related plant, Taxus baccata, contain a compound that can be convert ed in the laboratory to Taxol. Because the needles can be gathered without harming the plant, it is not necessary to kill trees to obtain the drug. Pacific yew bark being stripped for Taxol extraction ‘Taxol inhibits cell division by acting on microtubules, fa key component of the scaffolding of cells, Before cell division can take place, the cell must disassemble microtubule units, and Taxol prevents this dis: Because cancer cells divide faster than normal cells, the drug effectively controls their spread, ‘The remarkable success of Taxol in the treatment of breast and ovarian cancer has stimulated research ef forts to isolate and/or synthesize other substances that will act upon the human body in the same way and that may be even more effective anticancer agents than Taxol. ‘Test your knowledge with Problems 10-39 and 10-40, Organic chemists, howeve have not been satisfied with merely duplicat ing nature's compounds. They have also designed and synthesized compounds not found in nature. In fact, the majority of the more th ganic compounds are purely syntheti example, many modern drugs 10millio and do notexistin liv Valium, albuterol, Prozac, Zantac, Zolott, known! \gorganisms. For Lasix, Viagra, and Enovid—are synthetic organic compounds not found in Scanned with CamScannerScanned with CamScannerScanned with CamScanner266) Chapter 10 Organic Chemisty Functional group An atom or group of atoms within a molecule that shows a characteristic set of predictable physical and chemical behaviors ? ional Group * 10-4 What Is a Functio! he sean compound have ‘As noted earlier in this chapter, more thar | ¢, 1t might seem an almost Wi cd by organic operties of so many com. decpeasbte tak sont ‘ie physical and ae) at - ones eta ee pounds, Fortuniately, the study of organi comp n undergo a wide variet, punds ca task as you might think While onan co Be ee ie lepo ean of chemical reactions, only certain portior ips of atoms of an organic mo}, ransformations. We call the atoms or Bro he f a eaictiat oe} *diaable chemical rere ‘i cane eee s rete will see, the same functional group, in whatever te curs, Slate tesaurin abs ‘of chemical reactions. mere rd sie have i, y the chemieal reactions of even a fraction of the 19 my ganic aan a "inate ay e need to identify only a few cae nn functional compounds, Instead, we r oy ae el Naps study the chemical reactions that eacl é , Foe ne en ie ew also important because they are the nits by which we divide organic compounds into families of ‘compounds. For example, we group those rand that contain an —OH (hydroxyl) group bonded to a tetrahedral carbon into a family called alcohols; separa teint fa —COOH (carboxyl group) belong to.a family called carboxylic acids. Table 10-3 introduces seven of the most common functional groups. A complete list of all functional groups that we will study appears on the inside back cover of the text. Table 10-3 Seven Common Functional Groups Functional Bamnilys 2s Group ici: exmmpless als Name eae ‘Aleohol —oH CH,CH,OH Ethanol ae —NH, CH,CH.NH, Ethylamine fe 1 I ‘Aldehyde —C-H CH,CH Acetaldehyde fe) ‘oO I I Retin —c— CH,CCH, Acetone 9 9 2 U Carboxylieacid ~=©§—C—OH _CH,COR ie ac ° BS Acetic acid = Ester ~C—OR cutocn,cx, ; ° Amide —C—NH, oe ee AL this point, our concern las of molecules contail” of these and several other fuy ‘ay about the physical and nies Funetional groups algy ane etD8! BtOUps in Chapters sige Boner serve as th, ipters L119, dell each of the 10 million or aes Jor naming organic compound willshow how the nme ate of every athe eat 1 " i ° g c Vidal fanetional groups in detage ve 12 Chapters 1]. eene oeTo summarize, functional groups: * Are sites of predictable chemical reactions—a particular functional group, in whatever compound it is found, undergoes the same types of chemical reactions, * Determine in large measu the physical properties of a compound. * Serve as the units by which we classify organic compounds into families, * Serve as a basis for naming organic compounds. A. Alcohols As previously mentioned, the functional group of an aleohol is an —OH. (hydroxyl) group bonded to a tetrahedral carbon atom (a carbon having bonds to four atoms), In the general formula of an alcohol (shown below on. the left), the symbol R— indicates a carbon group. The important point of the general structure is the —OH group bonded to a tetrahedral carbon atom. R Hu n-G-O-8 H-CqRSO=H, CH,CH,OH HOH Condensed An aleohol ‘Here we represent the alcohol as a condensed structural formula, (CH,CH.OH. In a condensed structural formula, CH; indicates a carbon bonded to three hydrogens, CH, indicates a carbon bonded to two hydro- gens, and CH indicates a carbon bonded to one hydrogen. Unshared pairs of electrons are generally not shown in condensed structural formulas. Alcohols are classified as primary (1°), secondary (2*), or tertiary (3°), depending on the number of carbon atoms bonded to the carbon bearing the —OH group. H H CH, cH,—C—on om on auton H én, CH, Av alechol A. 2 alcohol 3° aeobol : Drawing Structural Formulas of Alcohols ‘Draw Lewis structures and condensed structural formulas for the two ‘aleohols with the molecular formula C3H,O. Classify each as primary, . secondary, or tertiary. Strategy and Solution Begin by drawing the three carbon atoms in a chain, The oxygen atom of the hydroxyl group may be bonded to the carbon chain at two different positions on the chain; either to an end carbon or to the middle carbon, on | c—c—C C—C—C—OH cto Carboo ahain ‘Te twa locations for tho — OH growp | Finally, add seven more hydrogens, giving a total of eight as shown in the ‘molecular formula. Show unshared electron pairs on the Lewis structures: | but not on the condensed structural formulas, 10-4 What Is » Functional Group? (267) Alcohol A compound containing ‘an —OH (hydroxyl) group bonded to a tetrahedral carbon atom —OH (hydroxyl) group ‘An —OH group bonded to a tetrahedral carbon atom Scanned with CamScannerBEB} Chapter 10 Organic Chemisty aleobol) is Amine An organic compound in which one, two, or three hydrogens of ammonia are replaced by carbon groups; RNH,, R.NH, or R,N Amino group A nitrogen atom bonded to one, two, or three R groups, RNH,, RLNH, or RN, where the symbol R represents a carbon group. surat Ball-and-tick models Les birabures conent z Hu 4 1-6—6- ga on,cH,cHOH i r Hud ae OH 3H,CHCH, A second x , 1, whosé common name is isopropyl ‘The secondary aleohol 2-propanol tae taste alcohol, is the cooling, soothing component in Ful Problem 10-2 Draw Lewis structures and condensed structural formulas for the four alcohols with the molecular formula CH1,j0. Classify each aleobol 28 pri mary, secondary or tertiary. Hint: First consider the connectivity of the four carbon atoms; they can be bonded either four in a chain or three in a jn with the fourth carbon as a branch on the middle carbon. Then consider the points at which the —OH group can be bonded to each carbon chain.) B. Amines The functional group of an amine is an amino group—a nitrogen atom bonded to one, two, or three carbon atoms. In a primary (1°) amine, nitro- gen is bonded to two hydrogens and one carbon group. In a secondary (2°) amine, it is bonded to one hydrogen and two carbon groups. In 2 tertiary (8*) amine, it is bonded to three carbon groups. The second and third structural formulas can be written in a more abbreviated form by collecting the CH, groups and writing them as (CH,);NH and (CH,),N respectively. The latter are known as condensed structural formulas. ; es ; ; a : : CHNHY CHANEL or (CH,).NRI CH, CHJNCH, or (CH, CH, Trimeth Methylamio lamin ede Orawing Structural Formulas of Amines Draw condensed structural formul as for the two pr : molecular formula CsHJN © Oo primary amines with the Strategy and Solution » For a primary amine, draw a nity nat Por Tomen atom bonded to two hydrogens and one Scanned with CamScanner10-4 What Is a Functional Group? | 269 y NR, i NH, c-C-C—NH, C-C—¢ CH,CH,CH,NA, CH,CHCH, Tie ket eaten ttay Ai seven ydragens ta jeeaeh carb fur vpielll Ceneenin Gras nad ogee adie eae Problem 10-3 Draw structural formulas for the three secondary amines with the molecular for- mula CHyN. C. Aldehydes and Ketones Both aldehydes and ketones contain a C—O (earbonyl group). In formal- : dehyde, the simplest aldehyde, the carbonyl group ie bonded to bea fnyairgs 5). OrBORyLaTOUR, A030 err gens. In all other aldehydes the carbonyl group is bonded to one hydrogen Aldehyde A compound containing and one carbon group. In a condensed structural formula, the aldehyde 4 carbonyl group bonded to < group may ' written showing the carbon-oxygen double bond as CHO or, _Ydregen; a CHO group alternatively, it may be written —CHO. The functional group of a ketone is a carbonyl group bonded to two carbon atoms. In the general structural Ketone A compound containing formula of each functional group, we use the symbol R to represent other carbon groups, roups bonded to carbon to complete the tetravalence of carbon. R o oO 1 iy I ae R-C-L02Hi CH, $O=HI R G— CH, SG5-CH, R F Accialcyet Acsione : nidehy ketone Drawing Structural Formulas of Aldehydes Draw condensed structural formulas for the two aldehydes with the molecular formula C,H.0. Strategy and Solution First draw the functional group of an aldehyde and then add the remain- ing carbons. These may be bonded in two ways. Then add seven hydro- gens to complete the tetravalence of each carbon. cen CH,CHCHO Heel 6 os CH, Scanned with CamScannertional group of a carboxylic acid is a ~COOH (carboxy) tural formula, a car. hydroxyl) group. In a condensed struc also be written —CO.H. Scanned with CamScannerScanned with CamScanner