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CLASSIFICATION # & OF ORGANIC COMPOUNDS gg >-e uc ‘ctr methyichioride =~ Each different arrangement of atoms corresponds to a different compound and each compound has its own characteristic set of physical and chemical properties. methytamine Classes or Families of Organic Compounds * Organic compounds are divided into classes or families of compounds according to the functional groups they contain. “+ Functional group » Responsible for the characteristic properties of the compound >» Most reactive part of the compound / Act as the reactive site of the compound. A functional group is the part of molecule having a special arrangement of atoms that is largely responsible for the chemical behavior of the parent molecule. Classes or Families of Organic Compounds |The Hydrocarbons * compounds containing only C & H A. Aliphatic HC’s * do not contain the benzene unit 1. Acyclic (or open-chain structure) HC's a. Alkanes « all -E-C- single bond b. alkenes « with -C=¢- double bond c. Alkynes © with -C=C- triple bond 2. Alieyclic (or cyclic structure) HC's Cycloalkanes, Cycloalkenes & Cycloalkynes B. Aromatic HC's 1. Mononuclear « contains 1 single benzene nucleus 2. Polynuclear * contains 2 or more benzene unit 3. Alkyl aromatics Hydrocarbons Hydrides of C > Simplest of organic compounds » Form basis of C skeleton to which other functional groups are attached. hall-and-stick model of decane Alkanes or paraffins = Open-chain structure = Saturated HC i.e, All Cap? = Low affinity ® i.e., unreactive chemically to most reagents = Type formula, CyHonyo 2.8. Cy + Hayes = CH Cat Howie = CoH Cy#H Cat Hajajea = Ca 6 aia}ea = crt ‘Homologs * Homologous series + Series of compounds with similar structural features in which each molecule differs from the next member by a constant amount of atoms. » They have properties that vary in aregular and predictable manner. & e.g. n-Alkanes « Each alkane differs from the next member by a -CH, unit Nomenclature « system of naming Molecular Structural Commonor IUPAC formula formula trivial name k methane methane H-C-H H CiH, CH;CH; ethane ethane sH, CH;CH,CH, propane propane name [Kekust structure condensed structure: balkand-stick modet H jnethane nou cu h HOW foe ec UR au wn propane H fet CHACH.CH, HHO ma ee foustarne reg ee CECHACHCHs Hund Alkanes or Paraffins Molecular Structural Common or IUPAC formula formula trivial name CyHyy CH,CH,CH,CH, n-butane butane ‘continuous’ chain CH;CHCH, isobutane — 2-methyl- CH, propane ‘branched’ chain (No. 2 may be omitted) +H Alkane — Alkyl radical (C Hanes) (C Hansa! H Alkanes or Paraffins |... Methane — Methyl radical cH, CH, Molecular Structural formula Common or IUPAC formula trivialname Csi CH5CH,CH,CH,CH, n-pentane pentane CH3CHCH,CH3 iso-pentané — 2-methyl- CH butane Hs, neopentane —2,2-dimethyl- CH3C-CHy propane CH IUPAC Rules 1. Know suffix ending, e.g., -ane for alkane. 2. Look for the longest continuous chain = Parent chain. 3. Number C chain such that substituents gets lowest possible no. = (All unnumbered C’s are substituents.) 4, Add substituent to parent name. 5. Numbers are separated from each other by a comma and from words by a dash line. [substituent] {parent hydrocarbon] [functional group suffix] Alkanes or Paraffins Molecular Structural Common or IuPAC formula formula trivial name CoHsa COOL CO-CCC é c °F cc COC t possible structural c isomers of CCC CHis é Alkyl! Radicals Classification © Primary, 1°C or 12 RCHY = Attached ta one other C atom > Secondary, 2°C or 2° R,CH- = Attached to two other C atoms » Tertiary, 3°C or 3° R,C- = Attached to three other R— any alkyl group 3 primary carbon) CH,CH,CH,— # propyl group 3 secondary carben | cao, an isopropyl group Catoms Alkyl Radicals Alkane Alkyl radicals CHy “CH; (methyl) CH,CH, -CH,CH, (ethyl) | CH3CH,CH3 -CH,CH,CH, CH,CHCH, (n-propyl) (iso-propyl) CH3CH3CH,CHs ~CH;CHyCH CH CH;CHCH,CH; (n-butyl) (sec-butyl) CHA GHCHs -CH,GHCH, CH3C-CHy CH, CH, CHy liso-butyl) (t-butyl) Alkyl Radicals [2 primary carbon] | [aprimary carbon) [a secondary carbon] [1a tertiary carbon | CH, (CH,CH;CHCH)— CRANE CHACHA CH: CH; CH: CHy a butyl group an isobutyl group: asec-butyl group a tert-butyl group) e.g. CH3;CH,CH,CH,CH-CH,CH,CH,CH,CH; CH;CH-CH,CH, 5-sec.butyldecane or 5-(1-methylpropyljdecane Cycloalkanes = Has aring * Saturated HC (i.e., All Csp*) cyclopropane * Type formula, C,H,, or (CH5)n : Ae. ng fe Hae ae Hc Fae Hy Be _ehy H,C—CH; H,C—CH; H.C —CH; CH cyclopropane cydobutane cyclopentane cyclohexane A Oo co © cyslopropane cyclobutane cyclapentane tydohexane Unsaturated Hydrocarbons * Alkenes or olefins * Cycloalkenes > Open-chain structure ® Cyclic structure > Type formula, CHa, Type formula, C.Ho.9 O ®& CH;CHACH.CH.CH, = CICH,CH,CH = CH) an alkane an alkene acyclicalkane acyclic alkene CsHip CcHip CoHig eHa Coan CyHin Cota CoHn-2 Unsaturated Hydrocarbons HC=CH) — CH,CH=CH; QO O systematicname, ethene propene cyclopentene ——_cyclehexene common name: ethylene propylene RCH3,—CH—CH — H5R H)C=CH— — HyC=CHCH)— the vinyl group the ally! group H,C=CHC H,C=CHCH,Br systematic name: chloroethene 3-bromaprapene common name: — vinyl chloride allyl bromide Alkene Number the longest continuous chain containing the functional group in the direction that gives the functional group suffix the lowest possible number. ‘itty! ths Bags Bek Tee ore lor ee CHCHCH=CH, = CH,CH=CHCH, = CH,CH=CHCH,CH,CH, y-butene 2butene Bhexene i ae SCH ‘the longest continuous chain has eight carbon: CH CH;CH)CHYCH,CH;CHy id hace pea i tat, ‘the functional group has six carbons, 30 the aber wheels parent name cf the compound is hevene Alkadienes (or Dienes) = Contains two C=C = Type formula C,H,,,5 > Isomeric with cycloalkenes & alkynes Kinds of Alkadienes > Based on the relative position of the C=C slong the C chain double bands are double banat are_ separated by one Soren eney single bond than one single bend CHCH=CH—CH=CHCH, CHy=CHCHy @ conjugated diene an Isolated diene Different Kinds of Dienes 1. Cumulated dienes * two double bonds occur successively * also known as allenes ee H.C = C= CH, HyC=C=CH-CHs sp? sp sp? 123 4 Allene or propadiene 1,2-butadiene 2. Conjugated dienes « Alternating double & single bonds * Forms delocelized 7 m.o. eg. 13-butadiene 3. Isolated dienes * Double bonds separated by two or more single bonds Dienes ms .f a i , CH=C=cH, tay-b—tu=cu, Bre t Lemethyl1 butadiene —_S-bromo-1,2-cyddohéxadiene or or systematie: —_propadiene DLmethylbuts-1.3-diene —_S-bromocydohexa-12diene common: allene 6 4 CH\CH=CHCH, i: Dimethyl Ahexadiene | Sathyl: nati heptane or 2-methythena-1,4-diene S-ethyk 2metiyinepta-24-dlene Alkynes = Has a - at = Type formula C,H,,> * Due te linearity of molecule no geometric isomerism -hexyne a terminal alkyne 2heryna an internat alkyne Alkynes Molecular Structural Common or IUPAC formula formula trivial name GH; 4 acetylene ethyne CH. CH,-CEC-H allylene propyne City CH,CH,-CEC-H L-butyne (Aterminal alkyne) CH, 2-butyne ‘minal alkyne} Alkynes 43 HCSCH CH,CH,CS ‘H Systematic ethyne ‘batyne 4-methy-2-hexyne Common: acetylene —ethylacetylene = ethylmethylacstylene ——_ser-burtyimethy- aleritatakyee " anruareal iyse etyione He=ccn;— 1yC=CHcH,— propargyl group ally! group HC==CCHBr H.C =CHCH.OH jproparay! bromide allyl slcohol Alkenyne Peo Soa 3 1 ge 8? CH,CH=CHCH,CH.C=CH CH, =CHCH,CH,C=CCH, 5-hepten-l-yne ‘T-hepten-S-yne not 2-hepten-6-yne not 6-hepten-2-yne because 122 because 1<2 CH CH )CH,CH; CH, —CHCHC=CCH, i Sa se hexen-d-yne the longest continuous chain has eight carbons, but the &-carbon chain does not contain both functional groups; therefore, the compound [s named as a hexenyne because the longest continuous chain containing both functional groups has six carbons 4 12 8 56 6 54 8 2 4 CH,CH=CHC=CCH, = HC=CCH,CH;CH=CH, Zhexent-yne Thexen-5-yne not d-hexen-2-yne not S-hexen-1-yne Aromatic Hydrocarbons naphthalene phenanthrene chrysene Alkyl halides, RX where X =F, Cl, Br, | > Fis the smallest & the most electronegative. > lis the biggest & the most polarizable. Examples Hct methyl chloride chloromethane cHcl, chloroform cl, carbon tetrachloride » CHF ‘math fluor cna aaa cloride CUB meth! bromide au meth odie Alkyl halides, RX ‘@ primary carbon @ secondary carbon ‘@ tertiary carbon: R—CH)—Br R—CH—R R-—C-R ft t 4 primary alky! halide a secondary alky! hatide 4 tertiary alkyl halide: (ao te “The number of alkyl - groups attached to the carbon to which the cr halogen is bonded ; determines whether an alkyl halide is 1°, 2° ar 3°. isopropyl chioride isopropyl chloride Alkyl halide CHCl CHCHE CH.CHI CHICHLCHBs common name: methyl hloride ethyl fluoride ih CHs ‘systematic name: chloromethane fluoreethane - “ isopropy! bodide: sec-buty! bromide Exercises a Compound Common name IUPAC CHsCH-CH,Br CH, (CH,),CCl {CH,);CCH,I | AL NO, Classes or Families of Organic Compounds Il. Oxygen - containing compounds A. Alcohols, or R-OH ( -C-O-H), Enols (3C=C<) O-H Phenols or Ar-OH [{ (O}-0-n) B. Ethers (R-O-R') C. Carbonyl compounds “a “ 1. Aldehydes (R-C-H } 2. Ketones (R-C-R’) R stands for alkyl group while Ar stands for aryl group Classes or Families of Organic Compounds II. Oxygen - containing compounds D. Carboxylic acids & Acid derivatives P 1. Carboxylic acids ( R-C-O-# } 9 2. Acid halides { R-CX) 3. Amides ( R-C-NH,, R-C-NHR’, R-C-NR’R") a 4. Esters ( R-C-O-R’) o oO 5. Anhydrides ( r-o-4p’) R stands for alkyl group while Ar stands for aryl group. Oxygen-Containing Compounds + Hydroxyl group (-O-H) as functional group ® Considered derivatives of H-O-H = (v-shaped * bond ap or phenyl- GOH —_ a> methanol => aa Ea eur CH, —CHCHR an allylic cation a benzylic eation Alcohols, R-OH Leaegna scaraeac aa CHEE CH,CH,CH;CHCH,OH (CH, CHyCH;CH,0CH,CH,CH,OH OH H2CHy 2-butanol 2eethyh-t-pentanal 2 -butody.t-propariol of ot or butan-2-01 2ethylpentan-tal Z-butoxypropan-t.ol ______ —— The longest continuous chain ‘The longest continuous chain has six carbons, but the fongest has four carbons, but the longest continueus chain containing the continuous. chain containing the OH functional group has five: OH functional group has three: carbons so the compound is ‘carbons, 9 the compound is named asa pentanol, | [named as a propanol, CH, ede 3 AB a Per ee oe HOCH:CH:CH:Br — CICH,CH:CHCHs CHAECH:CHCH OH CH, OH 3-bromo-1-prapanol A-chloro-2-butanol 4,4-dimethyl-2-pentanol Phenols, Ar-OH OH = og Ethers, R — O — R’ forAr) {(orAr’) + Divalent oxygen ® (-O-) es functional group ® Ethers are also considered as derivatives of HO where both H's of water are replaced by alkyl/aryl group _— $f ot simethyl ether oe R-OR R-0-B° [asymmetrical thar an unspremetiicat ether | ‘Symmetrical or simple ether > R's the same Unsymmetrical or mixed ether > 2 R's different, Ethers Compound Name Classification CH,-O-CH, dimethyl ether dialkyl ether methoxy methane 3c-0-¢ sp? sp? CH3-O-CH,CHs ethylmethyl ether methoxy ethane methyl phenyl ether alkylaryl ether: cH 0X2) methoxy benzene yoked anisole sp? diphenyl ether diaryl ether: QS) skomoeure — NSS) Ethers CH, | CH,OCH;CH; CH,CH,OCH,CH; CH CHCH;OCCH; ethyl methyl ether diethyl ether | | often called ethyl ether CH, CH, tert-butyl Isabutyl ether i CH CCH CH;CHCH,CH. wt > I CH, CHy sec-butyl isopropyl ether cyclohexyl isopenty| ether Alkoxy radicals cH; CH,O— CH,CH,O— CH,CHO— CH;CH,CHO— cHdo— methoxy ethoxy: ae te dis isopropoxy sec-butoxy ‘tert-butoxy CH,CHCH,CHy CH CHCHO Cray 4 CH; 2-methoxybutane {-ethoxy-3-methylpentane oe ] 14-dilsopropoxybutane Exercises Name snd classify ree KK AAs Cyclic ethers a zs a ciara tng Ly as ~\ epoxides tetrahydrofuran pyran in é ae o pC —CHy és = f HC—CHCH ethylene oxide propylene Galie Ethers Example a a 3-chloro-1,2-epoxyprapane cl o b AN A fy At H,C—CHCH,CH; CH,CH—CcHCH; H,C—C Zethyloxirane 2,2-dimethyloxirane CH, 1,2-0poxybutane 2,3-epoxybutane 2,2.dimethyloxirane 1,2-epoxy-2-methyl propane Carbonyl Compounds Aldehydes Ketones oO oO il Il © we 4a K “H KR an aldehyde aketone a It a |a carbonyl group. acyl groups - Functional isomers: CH,CH,CHO & CH,COCH, 1 1 Cc Cc C OH oe formaldehyde an aldehyde a ketone acetaldehyde formaldehyde acetone Aldehydes Compound — Common name IUPAC HzO formaldehyde methanal x CHyf=0 acetaldehyde ethanal # CHSCHaf=0 propionaldehyde —_propanal aliphatic # aldehyde CHaletag=0 butyraldehyde butanal CH,(CHy),=0 _valeraldehyde pentanal #H Ay ay CHLCH systematic name: mathanal thanal Ws common name: formaldehyde acetaldehyde 2-bromepropanal -bromopropionaldehyde | evn gS cl CH; systematic name: @-chtorabutanal 2. methylbutanal hexanedtal common name: é-chioratutyraidshyde —_—_isovaleraldehyde SCH, systematic name: cominen rain: trans-2-mothylcyctolvexanecarbaldehyde Q bengenecarb aldehyde benzaidtan ‘Aromatic aldehyde Exercises CH,CH,CHCH,CH,C=O ‘ A CH, H nS H CH CHS CHCH; oO 3-pentenal Zp 4 Aca \ H jO benzaldehyde phenyl- Aromatic CH methanal aldehyde Ketones Compound Common name IUPAC Classification CHap=O dimethylketone — propanone CH; or acetone CHyp=O butanone L methyl ketones CHCHs CH3£=0 R(any} CH,C=0 2-pentanone CH)CH,CHs CH3CH3P=0 3-pentanone CH,CHs cH, | ct CHsCHy — CHyCHyCHs CH,CHCH;CH;CH; systematic name: iced Zhexanene 6-methyl2-heptanone jana derived name: Pecan ‘ethy| propyl ketone isohexy methyl ketone CH Cy & Se CH; CH “CH, © CHYCH=CHCHS "CH, Isystematicname: eyeiehexanone —butanedione: 2Apentanedione ALhexen- done jcommen name; acetviacetone: ‘Aromatic ketones “CH; CY Duce fc C C common name: acetophenone ‘butyraphenane henzophenons derived name: methyl phenyl ketone Phenyl propyl ketone diphenyl ketone Carboxylic Acid a R—- (or Ar) OH a carboxylic acid Oo ] c FN OH a carboxyl group Carboxylic Acids 9 o o o I 1 i i c. c. c. c 4” “OH CHy “OH -CH,CHY “OH — CH.CH,CHS “OH gystematicname: methanoicacld —ethaneic acid prepancte acl utancis ach common name: — formic acd smeticacid = propionic acl butyric ace 0 0 1 1 c 45 \CH,CHCH.CHS "OH CH,CH:CH.CH,CHy “OH = CH)=CH™ “OH _y “oH pentanoic acid hexandic sci propencit ackt —enzenocarboxylic ac valenicacd ‘apraic acc acrylic acid wenzole af oO oO IL Il c (CH\CH,CHSCHSCH,” | "OH = CH,CH)CHCH,CH; “OH Roe as 2 - 8 oy Be [systematic nomenciature | [common nomencisture 9 9 0 cao | Br el ] ees ic Kes CHCH.CH” “OH CH:CH,CHCHY “OH CHLCH,CHCH,CHY >OH systematk ame: 24nethoxybutencie acid Jbromopentanaic acéd A-chlorohexanoic acid ‘common name: a-methoxyoutyric acid -bremovaleric acid ‘y-chiorocaprolc acid a a coon ©. coon oN “OH x rr CHy COOH Gachexancearboxylé add traas-methyleydopentanccartaxyile —1,24-benzenelviearboxylie ad pry 0 oO oO i i i a’ Nt cHy “ort cy So Nat systematic name: sodluin wethanoate ——potasslum ethanoate sodium benzeriecartionylate common name: — sodium tomate potassium acetate sodium benzoate Fatty acids = Long chain carboxylic acids Examples: CH,(CH,),,COOH —CH,(CH,),,COOH CH, (CH,],CH=CH(CH,),COOH Lauric acid Palmitic acid Oleic acid Carboxylic acid derivatives Oo Class RC Zz Examples ‘ 2 x 20 20 Acid RC where Xis CH,-C. Sc halides x F.cl,Brl cl cl acetyl benzoyl! chloride or — chloride ethanoyl chloride an acyl chloride Acid Halides o i CH. , fae Ea [oe ons cay “Cl CH,CH;CHCH; = “Br a systematic name: ethanoyl chloride 3-methylpentanoyl bromide ——_eyclapentanecarbony! common name; acetyl chloride emethylvaleryl bromide chloride Carboxylic acid derivatives 2 Class RC Zz Examples Z a -OR' mal 2 Esters Ro alkoxy CHC-0 ¢S>-CO oR’ group CH,CH, CHSCH, Torben omveen | ethyl Ethyl acetateor benzoate athyl BS Or _|ethanoate carboxyl owaen Esters QO Q 9 : + J i CHY “OCH CH; CHCHY “OA, CHCHCH” “OCH: Co SOcH.cH; Ne SF lystematic mame: ethyl ethancate —phenjé propanoste—methy! bromobutanaste thy cyulohexanecsrbaryatk ‘commonimame: —eihylaceiste peng proctonats jetencbatyrte a oO Oo o o ¢ il ; rt A, ws ( A. 4 en CLACHy Dewaryelopantanans Qaxarydehexansne }:mathyl2erarytlohexanane 2-sihyl2-otacyelapontanene y-butyrelactona = sValarolactone S-aprolacone tamrolactone: Carboxylic acid derivatives Qo Class R-C Zz Examples ‘Z 0 Oo oO Amides RC -NH, CHC gS- “NH amino NH, NH, (or NHR? group Acetamide Benzamide NAR") an amide Amides < Ni CICHCHCHY NH, O ; I ~onc, Achiorotutanaride: eee dh] etyicydoneranecaronamid fystematicname: ettanarnise commoniname: acetamide s-chierobutpreside oO a I I An \ as om ICHSCH; mi) CHCH.CH;CH; HOHE CHCH CH? ~NCH;CH, CH, CH.CH, Ncyclohexyipropanamide ——_Neethy/¥+ methylpentanamide: N,Nfiothylbutanamide oO «on ‘ ek_Js # NH ‘i 2-azacyclohexanone 2-azacyclopentanone 2-azacyclobutanone 6-valerol. -y-butyrolactam 8-propiolactam Carboxylic acid derivatives no Class RC) Zz Examples Zz Acid = 2 22 2 anhydrides RC. on CH;C, =C ° 8 ? Roc carboxylate CHC. -< a group o acetic benzoic anhydrideor anhydride ethanoic anhydride aeeve annyerias Acid anhydrides Oo Oo oO oO I IL I I cuy “oO” “cu, cae 6" Ty systematicname: —ethanalc anhydride ethanolic methanole anhydride common name: —_acetic anhydride acetic formic anhydride asymmetrical anhydride amixed anhydride Classes or Families of Organic Compounds Ill. Nitrogen - cantaining compounds . Amines { -N-) . Imines ( C=N-H ) . Nitriles ( -C=N } . Aza compounds ( R-N=N-R ) . Diazo compounds (-N=N) —_[2N's ecoupy terminal position Azides ( -N=N=N ) 1. alkyl azide 2. acyl azide G. Hydrazones{ C=N-NH, } H. Oximes ( C=N-O-H } |. Nitro compounds (-NO3 } 7m OOM D> Nitrogen-Containing Compounds Amines * Trivalent nitrogen (-N-) as functional group = Considered as derivatives of ammonia, NH; Examples R R h NH; R—NH R—NH R-N-R ammonia aprimaryamine a seconderyamine —_—a tertiary amine * Classification depends on the no. of R groups directly attached to -N-; where R = alkyl/aryl itranen is attached tarbon is attached [Re eve alkyl groups ro thres aly! groups, re ae NH, Rec R-C—on AMINES a ees0sey aevina tertiary alkyl ehtonde a tertiary ateat Aliphatic CHSNH, CHjNHCH; CH3NCH; CH,CH-NH, ba, Hy Aromatic NH, hNHCH, -NICHs), N-methyl —-N|N-dimethy! Aniline Aniline qk oy « Amines CH;CH.NHy CHCH.CH NA, . ethylamine prosylarine isobutylami CH NH, CH,NHCH,CH,CH, © CH,CH,NHCH,CH, methylamine methylpropylamine dlethylamine cH, oh cH, CH,NCH, CH|NCH,CH,CH{CH,; (CH,CHNCH,CH,CH, trimethylam ine butyldimethylamine ethyimethylpropylamine Email ia ae we ior (CH,CH,CH;CHNH, © CH,CH,CHCH,CH,CH, CH,CH,CH,NCH,CH, eee huceycHy . butan-t-amine Neothyl-3shexaneenine Naathyl-lemathy|-l-propananina or or N-ethylhexen-3-amine [NarhylN-methylprapan-|-amine CH, 48. 12 3 4. sl6 CECI ANER Te ‘CHyCH CHCH,CHCH, a NHCH3CH; 3.chlore-W-methy!t-butansmine ——_N-ethyl-S-methyl-3-hexanamine Br CHACHs pode ay ae CHyCHCH,CHCH. EES HS & \ sercasiney CHWCH, 4-bromo-M,W-dimethyl-2-pentanamine 2-athyl-A-propylcydohexanamine in i eel Ho CHsCH)CH,—-N*-CH; Cl CH, CH,CH, tetramethylammonium hydroxide othyldimethylpropylammonium chloride Nitriles, R-C=N = Cyanide or cyano group {-C=N) as functional group Examples: CHACH),C=N CS><=N Cl Ay C=N NH, acetonitrile or pentanenitrile benzonitrile ethanenitrile Nitriles, R-C=N = Cyanide or cyano group (-C=N) as functional group Examples: CHA=N CH;=CHC=K gqstomaticrame: sthanentria——benzenecatboniile Emotiyhornentrle propenendtrite common name: acatontelle beraonitlie eanethnfeapreaitie cron meth aide phen cyankde isoheryl cyanide CH,(CH,),C=N cl pentenenitrile ae Sulfur-Containing Compounds Thiols or mercaptans, R—S—H (or Ar) = Sulfhydryl group (-S-H) as functional group = Sulfur analogs of alcohols S electronic configuration 1s? 2s? 2p® 3s? 3p? 3p? 3p? 3d? 3d° 3d? 3d° 3d° * The sulfur atom is just as electronegative as carbon but what accounts for the polarity of the -S-H bond is the delocalization of e-s to these vacant d's. Mercaptans CH,CH,-SH H, ethyl mercaptan or (CH,-CH-CH,-SH ethanethiol or thioethanol Clty | CH;CHSH — CHsCH)CH;SH CH,CHCH,CH)SH HSCH;CH,OH ethanethial |-propanethiol -mathy!-I-butanethiol 2-mertaptoethanal Sulfides or thioethers, R—S—R’ (or Ar) (or Ar’) = Divalent Sulfur (-S-) as functional group = Considered as derivatives of H,S Examples: CH,-5-CH,CH, fH ethyl methylthioethers © CH,-CH-CH,-S-CH,CH, T cc HH” aR} a thioester Oe oO toluene aniline benzenesultonic acd gm om ght gh om benzaldehyce = beraaic acid benzonitrile O- Oa a phenyl group. a benzyl group Exercises Identify the functional groups present in the ff. compounds Acetaminophen Adrenalin Aspirin oilof vanilla wintergreen DH O=§-H on UE-O-CHs ‘OCH; H-E=O ° OH cHs i Alkane ea sonyc—c ‘Aldehyde RCH —H bonds sal J Aline senef Ketone R i Alkyne —c=c— Carboxylic acid RCOH q Nitrile -c=N Ester RCOR i. Alkytnalige RX X=P.CLBrorl RCNH: o ides i Ether ROR oe RCRHR ° Alcohol ROH RENR; Amine (primary) RNHy Phenol ArOH Ar = €>- Asming (secondary) R:NH Aniline ArH ‘Amine (tertiary) aN Summary of Functional Group Nomenclature Class ‘Suffix Nanee Prefix Name Carboxylic acid oie acid Carbony’ Ester -ole Alkosycarbouyl Amide amide Amido Nitrile -nitvite Cyane Aldehyde -al Oxo 0) Aldehyde al Formy! (—CH—0) Ketone one Oxo 0) Alcohol ol Hydroxy | Amine ~armine Amine Ll Alkene ene Alkenyl ce: | Alkyar -yne Alkyayl Alkane ane Alkyl Biher se ‘Alkoxy Ally haticle = Halo Priorities of Functional Group Suffixes C=0 > OH > NH; > C=C = c= ‘the double bond is given priority over a tiple bond only when there is a tie ey Polyfunctional groups: * Order of preference: -COOH>-SO,H>-CONH,,-CN,-COOR>-CHO>-C=O>-N->- OH,-NH,,-R,-NO,,-X Group Priorities eee CHCH, ——-HO. cH PHC, On CHCHCHCHCHCHCH: 7h iz ‘OH CH; Br OH ethylS-methyleydohexanol3,4-dimethyleyelopemtanol &-bromo-4-cthyl-2heptanol CH; CLEC 3 CHEE CHA ECHACHCH, ss Cl OW OH CH | ‘OH 2-chiora-3-pentanal 2.methyl-4-heptanol 3-methyleydehexancl not not not 4-chiora-3-pentanol 6-methyl--heptanol S-methylcydchexanol Group Priorities fm CH»=CHCH;0H = CH,C=CHCH;CH,OH 2-propen-1-al 4-methyl-3-penten-1-ol not 1-propen-3-ol CO CH\CHsCHsCH)CHsCHCH=CHy 5 HCHCHACHE 3 a OH OH 1-octen-3-01 E-methyt-2-cydohexenai Group Priorities age OA~m dee 3-hydroxybutanal methyl S-oxopentanoate ‘ethyl 4-formythexanoate ys Jhon by systematic name: 4-oxopentanal methy| J-oxobutanoate 2{-oxopentyl)- cydohexanene Linkages = Ways of linking alkyl (or aryl) groups in an organic compound Structure Link R-O-R’ Ether linkage R-C-O-R" Ester linkage R-CNH-R” Amide linkage RO pe) Anhydride linkage R'-C=0 R-S-S-R" Disulfide linkage

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