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; - ; t . -, t Compoundsthatcontainthe Crqanic Acids. f,,,nltional group R-COOH are called organic a'cids,or carboxylic acids.The structuralformula ior the acid, or carboxyl,group is shown in Figure 9-6. Organic acids are named from the corresponding alkanesby replacing the final "e" u'ith tle ending "oic" and adding the u'ord "acid." The first two members of this series are methanoic acid, HCOOH, and ethanoic acid, CH3COOH. They are better known by their common names, formic acid and acetic acid (see Figure 9-7). ( ,P \" general structureof an organicacid. The Figure 9-6. .\ H_-C. // .o HOH Figure 9-7. Structurai acetic acid. formulas f /,o 9-c( rl' o of formic acid and An example of a long-chain organic acid is stearic acid, CrzHs;COOH, also called a fatty acid. Fatty acids are related to fats and are disc us se d o n page 74. QUESTIONS l. . Which is the formula for ethanol? H (1 )H- I C-oH I H TT | I '\ (o it-Q-Q-oH \;' - I | HH o (2)H-C\ ,// 'oH T p ,oru-t-{ | \o " H 2. The functional group -COOH is airvays found in an orsanic /C acid (2) alcohol (3) alkane (4) \-" rlku.rJ 3. Which.^compound has the general formula R-OH? I(f) metha.tol (2) methane (3) methanoic acjd (4) pYopene //\ 4. What is the formula for pentanol? (1) CsHl, (A ) ( 3) C4H1o ( 4) c 4 H s O H c5Hl ro H 5. A .particular arrangement of atoms that describes Organic ChemistrY ,/f\ for (L) methanol (2)i ethanoic acid (3) methanoic - (4) acid ethanol group atB. Compounds in which there is an -OH tached to a carbon atom at the end of a hydrocarbon chain are called i I ) orsanic acids (2) alkanes (3) aro m a t i c c o m p o u n d s ' @ R r i n 't r r v a l c o h o l s CF ORGANIC REACTICNS COMPOUNDS Reactions of organic compounds generally occur more slou'ly than do reactions of inorganic compounds. Organic reactions often involve.only the functional groupi of the reacting species. This Ieaves the greiter part of the reacting molecules reiatively unchanged during the course of the reaction. Ace tr c a cid ( e th a n o ic a cid ) I ormrc a c r o (met hano i c a c i d ) the propertiesof a.seriesof compounds,Suchasorganic acids or alcohols,is cailed a (1) carboxyl group (2) ,-\ ^ group (4) hvdroxvl functional methyl ero.rO($ group 6. The thi rd memberof the hompl ogousseri esof pri mary alcohois is (1) ethanol @furonunoi (3) butanol (4) propane 7. Acetic acid, CHTCOOH, is the common name Substitution Reactions. in Reactions which one kind of atom or group of atomsis replaced by anotherkind of atom or group of atoms are called substitutionreactions.Except for combustion and thermal decomposition,reactionsof saturated hydrocarbonsare usually substitution reactions in which one or more hydrogen atoms are replaced. When a halogenatom replacesa hydrogenatom in a saturatedhydrocarbon,halogen substitution is saidto haveoccurred.The products,calledhalogen derivatives,are named usihg a standardsystem. The suffix comes from the name of the straieht-chain alkane with the same number of carbon atoms.The prefix shows which atoms or functional'groups have been added and the carbon atom in the straight chain to'which they are attached.A few gxamplesof halogen derivatives are Shown.in Figure 9-8 on page 74. Note that structures(b) and (c) are isomers. Addition Reactions. The additionof one asX,.to an unsaturated or more atoms,"des.ignated at a double or triple b^ond molecille hydrocarbon is called an addition redction. As a result of addition reactions, the multiple bonds are broken and unsaturated molecules become saturated (see Figure 9-9, page 74). Addifion reactions have a high rate of reaction. Becauseaddition reactionstake place more easily than do substitution reactions, unsaturated comoounds tend to be more reactive than are satuiated compounds.For example, becausealkynes are more unsaturatedthan alkenes,they are generally more reactive than alkenes' 73 .E trr C]HH HCIH ri r H-C-C-C-H ttl CI-C-C-C-H llr lll HHH HHH ( b) I , l- dic hlor opr o p a n e ( a) 2 -ci r l o ropr opane The hvdrolysisof fatsby Saponification. ClHCl bases i s cal l ed saponi fi cati on. S oap, w hich is a sal t of a .l ong-chai n organi c aci d, i s produced when a fat (a glycerol stearate ester found in ani mal fat) i s saponi fi ed by hot al kal i (see pa ge 76) . rtl H-C-C-C-H lll HHH C 3H s(C rzH 3sC OO)3 + 3N aOH -> i,s di"hlltlp.op"'.'" fat Figure 9-8. Structuralformulas of three halogen der iv at iv es .( T he n u m b e rsi n th e n a m e s o f th e hal ogen derivativesidentify the specificcarbonatomsto which the halogen atoms are attached.) I C-*Xz ti ons to i ncrease the yi el d of ester by act ing as a dehydrating (water-removing) agent. N { any esters have pl easant aromas. The scent s of many fruits, flowers, and perfumes are due to esters. Fats are esters produced by the r eact ion ofgl ycerol , a tri hydroxy al cohol (see page 7 6) , and l ong-chai n organi c aci ds (see page 73). al kal i 3C rzH g;C OON a + C 3H5( O H) 3 soap gl y c erl ne In an excess Oxidation. of oxygen,saturated hydrocarbonsburn completelyto form carbon dioxide and water. li --. -C-C- CHn + 2O2 -' COz + 21120 ll XX Figure 9-9. An addition reaction. The burning of hydrocarbonsin a limited supply of oxygenma;' producecarbonmonoxide(CO) or carbon (C). 2CH4 + 3Oz --+ 2CO + 4H2O Addition of Flalogens. Halogen derivatives can be formed by the addition of halogens to unsaturated compounds, as well as by substitution reac t ions , T he a d d i ti o n , o f c h l o ri n e a n d bromi ne takes place at appreciable rates, even at room temperature. Iodine is less reactive than chlorine and br om ine i n a d d i ti o n re a c ti o n s . F t r y dr ogenati o n . T h e a d d i ti o n o fh y d ro g en to an uns at ur at ed m o l e c u l e i s c a l l e d h y d ro g enati on. Hydrogenation reactions usually require the pr es enc e of a c a ta l y s t a n d e l e v a te d te m p eratures. The compounds formed are usually saturated hy dr oc ar bon s . Fermentation. CH* + Oz--+ C + 2H2O Polymerization. Large molecuies can be formed from smaller molecuiesby polymerization reactions.The largemoleculesformedby poIymerization consist of chains of repeating smallersubunits.Suchlargemoleculesare called polgmers.Syntheticrubbersand plastics,suchas polyethylene,are polymers.Naturally occurring polymers include proteins. starches.and many other chemicalsproducedby living organisms. QUE'SrfOr{s The processin which en- zymes from living organismsact as catalystsin the partial breakdown of an organiccompound is called fermentation. Ethanol is a product of the fermentation of sugar(glucose)by yeast.The enzyme involved is calledzumase. CeHrzOo -----------.+ 2C2H'OH + 2COz sugar zymase ethanol jtrtff: l. The complete combustion of any hydrocarbonin excessoxygenproduces (1) CO and Hz (2) COz and H 2 (3) C O and H zO dZ) C O, and H zO 2. The correct name f#the compound shown below i s (1)_ 1,3-di chl oropentane(2) 2,4-di chlor opentane fiil1,3-dichlorotutane (4) 1,i-dichlorobutane \JZ ClHCI H Esterification. The reaction of an organic acid with an alcohol to form an ester and water is called esterification.Esters are covalenr compounds with the generalformula RCOOR'. The generai equation for esterificationis RCOOH + R,OHe2RCOOR,+ H2O orga.4rc a lco h o l e ste r water Esterificationproceedsslowly and is reversible. Sulfuric acid is often used in esterificationreac- 74 lltl H- C -C- tl tl C-C-H HHHH 3. In the preparationofan ester,the yield ofthe ester is increaselLbythe addition of (1) water (2) sodium chl ori de { 3))sul furi c aci d (4) sodi um hydroxide 4. The rei cti on C gH s + C l 2 + g.gt6l + HCI is an exampi e of @ substj tuti on (2) addi ti on (3) est er ification (4) hydrogenation Reaieuing Chemistry: Unit 9 I 5. Which equation represents an esterification reaction? (L) C6HreO6 -; 2C2H5OH + 2COz ( 2 ) CsHlo * H2 -+ CsHrz {3 ) C rHn - Clz --* C3 H?C I + HCI r{}n-coou + cH3oH--+HCoocH3 + HoH Bi u/ni.h structuralformularepresentsthe productof the reaction between ethene and bromine (Brz)? HH H I tr) Br---!-Br II H -_?-C -H ll Br I H Br with two -OH groups are dihydroxy3lcohols' with thiee -oH groups ar-e'trihvdroxv ;Jih;; s. alcohol *ef"oftoft are also classified a'ccordingto -the carbon chains attabhedto the carbon "t ""-L"i atom with the -OH groups' Alcoliols * Monohydroxy Alcohols. monony'dio"y that have one --OH group are alcohols. ."' * Frimarv Alcohols. Primarymop'6{yd'o*yaicohols *ere dis"ussedon paggif? In primary the -OH group-is,sf the last carbon "i""tt"f, The-general for;i"*trf in" hydrocar*bo" "4ui1 mula for a primary alcohpl'is R-CHzOH' SecondaryAlcohqlS. Alcohols in which the tlie -oH sroup is bonded to "".b;;;i;;'with secondary,4lat" called secondary-4li*" "t" "ill"d "lfr"i""rboq.atoms "ir-r"t the -OH.gro'up is seco,ridaryalcohols-, In "".uo",6to-t cohols. (see noilo"ut"d at Lheend ofa hydrocarbonchain f f *"."-S- i.01.The general fo rmula fo-rd'econdary * HBrBr H Br (3) t l "-?-1-u. HH lll o H-9-9-?-' ltl HHH In an aqueous solution, whicn- compound wili b e 7. cH3cooH acidic? @I csHs(oH)g (4)cHsoH (2) cH3cHzoH (3 ) The reaction CH4 + Br2 -+ CHgBr * HBr is an of (1) addition (2)hvdrogenation @sub"*".rrpl. stitution (4) PolYmerization 9. A reaction between CH3COOH and an alcohol The alcoholused in oroduced the esterCH3C'OOCH3. -($. 'CH.OH (2) C2H'OH (3) *^r the reaction C3 H TOH ( 4) CaHs O H 10. Which of the following structural formulas repres e n ts2 ,2- dic hlor oP r o Pa n e ? r\Ijrriu where\3tid wnere ttrt(zLHUrl. alcohols.,i's nrnrcfiou, "i"%rr"tr,rt gto"it ;;;.b'"; ;;i.;fi t-;;tpi'ol, (seeFigure 9-lI). 8. H -Re ,/"' Fisure 9-10. The general structure of gecbndarY alcohols ./ -t"/ H O HH/ Hcrcl T:'1'T (,) (2)H-c-c-c H-A-J-I-.-' *)H-J-l-tr-" I I I I " AAH R2 r\2 arehv- secondary.alAn exam-ple "gf'a alcohoI op cali also 9d"is ropvl "_i_IdL" -[" ' " l l ,,'H H HHHH H 2-propanol H C IH _ ttr @n-q-9-9-H rrrllll HCIH HCIHH l tli (a)rI-_Q'c-c__c-H HCIHH 11. Which kind oi reaction produces ethanol as one (2) saof t}e principal products? (l) elterification ponification (3) neutralization- (!)fermentation iZ. Which compound will-updergo a substitution reCHl (2) CzHa (3) with chlorine? (9 ^"tto., CsHn (4) C4H8 "/ {< CLASSESOE',ALCOHOLS Alcohols are classifigdaccordingto the number of -OH groups theiy'contain' Alcohols with one g.6"n a.erdo"ohydroxy alcohols, those -Off / Organic Cherrlistrg Figure"g-11. 2-ProPauol (Note tirat the 0H glottP is on tire sec carbon.) in which the caris bonded to three -OH bon atorn with the alcohols. tertiary led are atoms other carbon is alcohol tertiarY a r general 'foqnuia The formulait t!:y: R;Rrfi;Con. rrt'esrdrctural 11 tig,i*'g;-iz. nt,#^"tpt" of.atertiarv1!"h"":^:' *hi"h-it also know:r as tertlp.opdnol, ;-;;thyl ioH ,fl I il Rr-Q-Rn il 'Rs Figure 9-12. Structural formula of tertiary alcohols' ' tJ H OHH H l l l n 'l ' Q-Q-Q'jH I | -'"1 , ".rl,1,, ,r"-T-" resent a hydrogen atom or an-y- hydrocarbon fu:rctional sroup. The structu,"i--iot*"I" of the AI- il;; it tho-" in Figure9-16' from the correPPondingal"a1'" Thus' t"pr""i"gitte final "e" with k;;;;;"iitti -ti.*bti oi irt" group is methanal' iri" ;;';;;;; 3""h;1;;"ilia"irti"' ilbd6:;i;l"n it ^tto H .H aldehyde' Figure9-16. Functionalgroupof an Fieure 9-13. Tertiary butanol, or 2-methyi-2-propanol' is i tertia ry alc ohoi. ;;il""ffi;J"ir'irt"" tl) Figure.n glvcol(see- /P -"\r:' 2-methYl-2'ProPanol * DihydroxYAlcohols: "-6u-_gtoups know-n'as dihvare9:T*::"d'r:l:f,t""*t:i*" ""l"oholt,or as glvcols'The fr;;;:".'iiltvati"., commost important glycol is 1'2-ethanediol' knownasformaldehvde' pJ-',vl::I:l:,$;:, or iH.i:*ft,^,t*Y|*: groups are easl l y OX ure 9-l B ). and antl E t hy iene g l y c o l i s u s e d a s a c o o l a n t f r eez e in c a rs ' I I H-C-OH H-C-OH I is the Figure 9-I4. Ethylene glycol, or 1,2-ethanediol' alcohol' dihvdtoxY most widelY o."d x Trihvdroxv Alcohols' - compounds areknownastrigroups ;;";i;l'islh;"J-os most impor;t trihvdric, alcoholl'-The il;;;;", is 1'2,3-propanetriol' or ;i;"ii"l ;"*'il'h;;;;;t elvcerol (see Figure-g-ft' Fats q9 synthesized acids' clyceroi is also F.Jti."-i""'"tJt "t-Jotg^nic of faidigestion in aninrals' ^t "."J'"t"a"ct I I + HzO + oxidizing-+ R-C:O agent water aldehYde primarY alcoho] Fi gure 9-17. Synthesisof an aldehYde' p H -n-J:o + oxidizing agent bU to form an orFigure 9-18' Oxidationof an aldehyde ganrcaclo. o H-C-OH I H 1,2,3-ProPanetriol Glycerol is the Figure 9-I5. Glycerol, or 1,2,3-propanetriol' alc onor ' most imp or t ant t r ihy dr ox y * OTHERKINDSOF ORGANIC COMPOUNDS /o R-Ci or gal l l c ac i d al dehyde I ".^i .// H-C-OH H--C-OH the genCompounds.with AldehVdes. can repR aldehydes' are for-trt'un-CHO ,,. ' ..!, Rr-C-R, ofketones' Figure 9-19. The general structure kno wn as aceP ropanone' w hi ch i s commonl y tI: member ,of simplest useu ^ta wldely l s A cetone (see Fi gure 9-20)' .";;.:;' il" t,,.'- .4..i ..-= f I ,.-:* ,,,.€ .;i,l,i H Beneral Compound5 * Ketones. -rvith .the R3 arg hyRt.and kitones: are RTCORz formula rl!"t" 9-19 shows the func;;;;.b";'gto"pt tional group of ketones' I ::'::]:l:n a"a4 .' .:':l tt EthYlene glYcol . ,,# H. H I n ' ,.:.s>j liiF . .:' :j:::i? R-C-OH * ,'..i ,+ # ca.n!e svnthesizedUy tlt" oxidation Aldehy'des- h.ti group as a sol vent. TfrT "-T-.-T-H HH A cetone Figure 9-20. Acetone,or propanone' Reaieuing Chemistrg: Unit 9 ,+ a'i t; ':a ..:: J t-, Ketones can be synthesized by the oxidation of sec o n d a ry alc ohols ( s ee Fi g u re 9 -2 1 ). oHo I * oxidizing -, Rr-d-R2 Rr-C-Rz + H2O agent sec ondaly alc ohol wa te r ke to n e Figure 9-21. Synthesisof a ketone by the oxidationof a s e co n d a ryalc ohol. Compoundswith the generalfor* Ethers. mula RrOR2 are ethers.The Rr and Rz represent any hydrocarbon groups.The best-known ether is diethyl ether (CzHsOCgHs),which has been used as an anesthetic. Ethers can be synthesizedby the dehydration of primary alcohols(see Figure 9-22). Rr-oE * ,Addition Reactions. Pol;'merization that results from the joining ofmonomers of unsaturated compounds is called addition polymerization' The reaction occurs by the "opening" of double or triple bonds in the carbon chain (Figure 9-24). Vinyl plastics, such as polyethylene and polystyrene, are formed by'addition polymerization' nCzHq --+ (-CzHa-)" Figure 9-24. Somepolymersareproducedby addition pol l meri zati on. + HzO + R;IOHI-+ Rr-O-R2 plima l y a l c o l - r o l s reaction may be repeated many times to produce long-chain polymers. For polymerization to occ,tr, the monomers involved must have at least two functional groups. Materials formed by condensation polymerization include silicones, polyesters, pol yami des, phenol i c pl asti cs, and n) rons. * QUESTfONS wa te r ' e th e r Figure 9-22. Dehydration of primary alcoholsto produce ether. A polymer is a largemolecule * PolVmers. that is c5mposedof many repeating smallerunits called monomers. Naturaily occurring polymers include starch, ceilulose, proteins, and DNA' and nylon Synthetic polymers include polyeLhylene. ^ The processin which monomersarejoined together lo form polymers is called polgmerization. Folymerization may involve condensation or addition. L Which compound is a dihydroxy alcohol? (2) C3H5(OH)3 (1)A I(OH )3 (3)C a(oH )z @,czHa(oH): 2. Which compound i s a tri hydroxy al cohol ? glyceroi (2) butanol (3) ethanoi (4) methanol 10 3. Which structural formula below represents ethanediol? @ HH HH ll (r) H-q-9-oH ll T"I'T T,I4,, (3) H- C-C-C-H rtll H o-C- C - o l H HH llll + H o l -C -C -o H rlll lll (4) H-C-C-C-H rll HOHH HHH lll (2) H-C-C-C rll I H HHH HO H H + HzO HH dirner Figure 9-23. Monomers can b e tion poiymerization. Organic Chemistrg (I) H-C-C-OH HH llli HO-C-C-O-C-C-OH HH slrl? )r'loltonte r lnononlel' HHO H an aldehyde? 4. Which structuralformula represents HH HH HH * HO O H HH * Condensation Reactions. Polymerization that resuits from the bonding of monomersby a dehydration reaction is called condensationpolymerization (seeFigure 9.23).The condensation F {H ll (iz} H-c-Q-H \-/ll water' jo in e d b y co n d e n sa - *lll {rsl, H-C-C-H \./ | H (4) H- H I I I I H H C \ Cc-o )H tt T\W 5. Which is the structural formula for glycerol? .H (1 ) H I I I H-C-OH I H I H OH I n ,!,! (2) H-9-OH H-C-OH I ( 3) HO-C-OH (4) H-Q-9/-'Q-Q-H H . I '"@ rt-q-oH ,.."1 ,H-q-oH H - -*Q-=*An-alde+ryde-ca:r-be--oxidize&tc{om=tt)-:a*ke=**-- tone €)-an-ester-{3)@-_ --9. *Whi"h formula represents a ketone? (i) (2) crHscoOCH cH3cocH3 (3) C2H5COBf (4) C H 3C H O I0. The reaction representedby the equation below (2) fermentation (3) esterifiis .(t) Btonification catron (fl polymerization l' , H-C-OH I ll. H Which is t}le general formula for an ether? . ol (I) R-OH nC zH + -+ (-C zH + -)" e\ R-< Which is the formula of methanal? //,o G'ils-( \ H \ H I (a I{-9-oH I H o @ *,-*on (3) H-\ ,7, Which is a tertiary alcgholl ll"oq?H /i:DH-o4-C]" ' /l | | 'HHH 7B H (4)o,-8-^, H OH ,,,n-L{-" rll 1 I /o I O HO H (-1)eHseeorf-{2} CH'iorr"-'-^-*-. (4) H-f-H I H -{a.rIICooH"-.-€fcH.scHQ_. Reoieuing ChernistrE: Unit I