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by: Camren Romaguera

OrganicChemistry CHEM321

Camren Romaguera
GPA 3.8


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This 27 page Class Notes was uploaded by Camren Romaguera on Saturday September 19, 2015. The Class Notes belongs to CHEM321 at University of Delaware taught by Staff in Fall. Since its upload, it has received 61 views. For similar materials see /class/207127/chem321-university-of-delaware in Chemistry and Biochemistry at University of Delaware.


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Date Created: 09/19/15
Dr Schneider Chem 321 Reaction Guide for Chapters 911 Alkenes A Addition Reactions 1 HX Cl Markovnikov addition HCI N M M prone to rearrangements 2 Acid catalyzed hydration H30 Markovnikov addition AK m N prone to rearrangements 8 Hydroboration 1 8H3 2 H202 NaOH AntiMarkovnikov addition Ho NO rearrangements both faces may be attacked 4 Oxymercuration 1 HgOAc2 H20 Markovnikov addition Y m gtltO NO rearrangements both faces may be attacked 5 Hydrogenation H2 PdC Pt02 or FihCPh3P3 Syn Addition PdC H2 both faces may be attacked 6 Halogenation Brg CI2 etc Br Br Anti Addition via bromonium intermediate Cczl4 both faces may be attacked Br 7 Halogenation with competing Nucleophilic solvent BI 2 quot39OH H20 Br L quot39OR ROH Br Dr Schneider Chem 321 Reaction Guide for Chapters 911 Page 2 8 Epoxidation peracid CH3C03H CF3C03H MCPBA peracid A N Syn Addition gt N both faces may be attacked 8a Epoxide ring opening reactions 8a1 Acidic Conditions 0 NuH OH Nu attacks more subs carbon Nu 8a2 Basic Conditions 0 1 Nu39 HOgtltNU Nu attacks least subs carbon 9 Carbene Addition diazo compounds CHCI3 NaOH H CN Syn Addition hv JA both faces may be attacked 10 18 dipolar additions see notes for all examples 9 V W NNO N O N 11 Ozonolysis OOO 0 R 03 H gOY primary ozonide rearranges to ozonide 11a Ozonolysis followed by reductive step Zn H20 Zn CH3C02H H3CSCH3 Pd H2 0 1 03 O N pds ketones andor aldehydes 2 H3CSCH3 AH 11b Ozonolysis followed by oxidative step H202 o N pds ketones andor carboxylic acids 1 0a 0 2H202 LOH Dr Schneider Chem 321 Reaction Guide for Chapters 911 Page 3 12 cis 12 diol formation KMnO4 NaOH H20 1 OsO4 2 H20 Na2803 J 939 HO Syn Addition 2 H20 Nagso3 H N both faces may be attacked 0 Alkynes A Addition reactions 1 HX L39 anti addition further addition HB Br Markovnikov Addition N further addition 2 X2 Br Br Brz JgtltBr M Br H Br Br H N an addition further addition 8 Acid catalyzed hydration j E ltO C ketone eno 4 Oxymercuration HgOAc2 H3O O OH eno ketone 5 Hydroboration disiamylborane 1HB i i 2 OH gt O gt H 2 H202 NaOH H N eno N aldehyde Dr Schneider Chem 321 Reaction Guide for Chapters 911 Page 4 6 Hydrogenation 6a H2 PdC PdCi H2 NV 6b Pd CaC03 Pb Lindlar39s Catalyst H H N Pd CaCO3 Pb My Syn Addition 6c Na NH3 H Na NHj W Anti Addition H B Base catalyzed lsomerization via allene intermediate 1 KNH2 2 H o 2 Q quotI Radicals A A Pyrolysis N gt t CH3 followed by any of the following 1 hydrogen abstraction 2 disproportionation 8 Bicleavage 4 dimerization B Radical Addition of HBr via peroxides HBr ROOR MBr Anti Markovnikov Addition hv M C Allylic Bromination Br M Br2 dilute M hv Br NBS HBr trace N Ta h W V M IV Dienes A Addition of HX Br 0 HBr U Br 12 Addition 14 Addition B DielsAlder I A diene reacts from scis conformation endo approach is favored if Fl is an unsaturated substituent NUCLEOPHJLIC SUBSTITUTION REACTIONS ALKYL HALIDES Nucleophilic substitution reactions are an important class of reactions which allow the displacement of one mctional group or substituent on an sp3hybridized carbon atom with another Nu39 R3C X gt R3C Nu X The X group is called the leaving group In this experiment X is chloride but can be any group which can accommodate a negative charge X an anion is formed Nuz39 is the nucleophile and is characterized by having an unshared pair of electrons which form a new bond with the carbon atom Anions which can act as nucleophiles include halides cyanide hydroxide alkoxide and others Neutral compounds which can act as nucleophiles include amines alcohols and water with subsequent loss of a proton HNu R3C X gt R3C NuH X39 gt R3C Nu HX Two classes of nucleophilic substitutions occur at sp3hybridized carbons SM and 5N2 In this experiment you will investigate how reactivity and reaction rates are affected by the different structures of a group of alkyl chlorides under SN and SNZ conditions 3N2 Reactions SNZ reactions occur as a concerted process As the nucleophile approaches the carbon atom and bond forming begins bond breaking between the carbon atom and the leaving group occurs simultaneously r Jquot l l 639 Nu C x gt Nu c x gt Nu c x transition state Inverted con guration In the transition state both the nucleophile and leaving group are present hence the kinetics are bimolecular and the reaction rate is proportional to both the concentration of the substrate and the concentration of the nucleophile If you double the concentration of the nucleophilc or the substrate you double the reaction rate rate k Nu Substrate Factors other than reactant concentration that may affect SN2 reaction rates include 1 leaving group ability 2 nucleophilicity of the nucleophile 3 stereochemistry and 4 nature of the solvent 1 leaving group ability The more an X is able to accommodate a negative charge the better a leaving group it will be and the faster the reaction Anions of this type are weak bases review acids and their conjugate bases Leaving group ability in decreasing order is shown below for the halide series Note that HI is the strongest acid of the group so I is the weakest base and best leaving group I gt Br gtC139gtF39 2 nucleophilicity of the nucleophile In general the higher the basicity of a nucleophile the more active it will be in displacing 21 leaving group Therefore HO is a better nucleophile than Water because it is a stronger base Basicity thus nucleophilicity tends to decrease from left to right across the periodic table Nucleophilicity is shown below for a series of rst row elements HZN39 gt HO39 gt NH3 gt F gt H20 3 stereochemistry The incoming nucleophile can approach the reaction site only om the side opposite the leaving group Any sub stituents which can block or hinder the approach of the nucleophile will slow the reaction or prevent it from occurring altogether Thus SNZ reactions occur only at primary and secondary carbon atoms where the R groups do not impede the approach of the nucleophile but never at tertiary carbons R R l l RCHzX R CHzX RCHz X R primary secondary tertiary As a result of the backside attack by the nucleophile inversion of con guration Walden inversion always occurs in SNZ reactions 4 nature of the solvent The solvent in an 8N2 reaction must be polar enough to dissolve the nucleophile and stabilize anion formation but not so polar as to promote ionization of the substrate Usually polar aprotic solvents e g ethers or tertiary amides are favored SNl Reactions 39 r L39quot 39 39 I In contrast to SNZ reactions SNl reactions occur in two steps In the first step the rate determining step the substrate ionizes to form a carbocation and an anion from the leaving group In the second step the nucleophile attacks the carbocation forming product Nu R3C X gt R3C X gt R3C Nu X Since only the substrate is involved in the rate determining step the kinetics are unimolecular and the reaction rate is proportional only to substrate concentration rate k substrate Doubling the concentration of the substrate will double the rate of reaction but changing the concentration of the nucleophile will have no effect on reaction rate Notedo not confuse reaction rate with yield A slow reaction can give a high yield if given a su icient time to react Yield is also affected by isolation techniques which have nothing to do with reaction kinetics The SN mechanism is favored by any conditions which promote the formation of the carbocation The structure of the substrate is of primary importance Structures which ionize to form stable carbocations facilitate the SNl mechanism Carbocations of decreasing stability as follows R R l l Q C H2 gt R C CH2CHC H2 gt R CH gt RC H2 R allyl secondary primary benzyl termquot In general when a charged species a carbocation is being formed the delocalization of that charge over several atoms favors the formation of the charge The benzylic and allylic carbocations shown above appear to be primary carbocations but in fact are stabilized by resonance overlap with the pi electrons which delocalizes the positive charge Therefore their formation is favored and benzylic and allylic compounds readily undergo SNl reactions in addition to 8N2 reactions CH2CH CHz lt gt CH2CHCH2 Reactions at tertiary carbons also occur under SNl conditions First steric hinderance prevents 8N2 attack Second tertiary carbocations are stabilized by hyperconjugation overlap with the sigma electrons of the neighboring substituents which helps to delocalize the charge Thus nucleophilic substitution at a tertiary carbon occurs only by SNl chemistry CH3 CH2H I H CH3 c ltgt CH3 C r s CH3 CH3 Formation of secondary and primary carbocations is much less favored and SM reactions occur only in those cases where steric hinderance inhibits 8N2 attack and an alkyl shift leads to a more stable tertiary carbocation CH3 CH3 Nu I I Nu 39 CHsCCHZX gt CHj39C39CHz gt CHsCCHZCHs gt CHsCCHZCH3 I t CH3 CH3 CH3 CH3 prinme tertiary Lastly solvent can be important in facilitating an SNl reaction Solvents which can help stabilize the carbocation are generally used and include polar protic solvents such as alcohols and water The stereochemistry of SNl reactions is also different from that of SNZ reactions The positively charged carbon atoms of carbocations are 5512 hybridized and are planar all the sub stiments around the positively charged carbon atoms lie in the same plane The incoming nucleophile can approach the carbon atom from either side of the plane giving a product mixture which is 50 inverted and 50 retained con guration Such a mixture is called a racemate or racemic mixture The product om an optically active starting material will lose its optical activity under SNl conditions but show opposite optical activity under 8N2 Experiments Objective to determine the effects of structure on the rate of reaction of various alkyl chlorides under SNl and 8N2 conditions Materials and Equipment 1chlorobutane 2chlorobutane 2chloro2 methylpropane 3chloropropene allyl chloride 18 sodium iodide in acetone 1 silver nitrate in ethanol water bath or hot plates w 400 mL beaker thermometer small test tubes pasteur pipets and rubber bulbs test tube rack Students Reagents are water sensitive Please keep all containers closed as much as possible All glassware very clean and dry Procedures SNZ Reaction Iodide ion is an excellent nucleophile and will displace chloride from alkyl chlorides Acetone is used as a solvent because sodium iodide N a1 is readily soluble and the product sodium chloride NaCl is not Thus when NaI reacts with an alkyl chloride in acetone a positive indication of reaction is the formation of an insoluble white solid Anything from a slight haze to a heavy precipitate should be considered a positive result First set up a 50 C water bath Fill a 400mL beaker with ZOOmL water and place it on a hot plate setting of 2 to start Monitor the temperature with a thermometer Ifthe temperature rises above 50 C turn down the heat and add some cold water to adjust the temperature It is important not to overheat the bath because acetone readily evaporates and this may cause false positives Label four test tubes one for each alkyl chloride Add 25 drops of 18 NaI in acetone to each test tube Then add 6 drops of the appropriate alkyl chloride to each tube and mix by shaking back and forth noting the time of addition If a precipitate forms on the addition of the rst few drops but redissolves on shaking ignore this Time 2 minutes and note any changes If nothing has happened place the tubes in the water bath and again note the time to any changes It is important to stay focused because changes may occur rapidly Heat no longer than 5 minutes Record the time to form a precipitate and under what conditions for each alkyl chloride Repeat the above experiment with 25 drops NaI in acetone and 18 drops of each alkyl chloride SNl Reaction In the reaction of an alkyl chloride with silver nitrate AgN03 to form silver chloride and an alkyl nitrate the silver atom coordinates With the chloride facilitating the formation of the carbocation Nitrate ion is such a Weak nucleophile that direct 8N2 displacement cannot occur RSC c1 AgN03 R3C AgCl No l AgNO3 in ethanol is strictly SNl conditions Again a positive indication of reaction is the formation of a white precipitate AgCl ranging from a haze to a heavy solid Ignore any precipitate which redissolves on mixing Label four test tubes one for each alkyl chloride and add 25 drops 1 AgNO3 in ethanol to each Then add 6 drops of the appropriate alkyl chloride to each tube with shaking and note the time of additions Time 2 minutes If no change has occurred place the tubes in the water bath and note the time to any changes Heat no longer than 5 minutes Clean Up Wash the test tubes into the waste solvent container Glassware must be free of all chemical residue and contaminants before disposal in solid waste container Pre lab Questions Draw the structures of the alkyl chlorides in this lab and label the substitution primary secondary tertiary allyl Rank the order of reactivity you expect fastest to slowest for the alkyl chlorides when reacted with NaI in acetone Rank the order of reactivity you expect fastest to slowest for the alkyl chlorides when reacted with AgNOg in ethanol Predict the change if any in the following rates of reaction a The concentration of Nal reacted with lchlorobutane is doubled b The concentration of NaI reacted with l chlorobutane is doubled and the concentration of lchlorobutane is halved Postlab Questions Did your results con rm your expectations for the reactivity of the alkyl chlorides with Nal Did your results con rm your expectations for the reactivity of the alkyl chlorides with AgNO3 What changes in the rate of reaction occurred if any when the concentration of alkyl chloride was tripled in the reaction with NaI Alkane Nomenclature Example name Rules Br 1 2 3 1 Longest chain of carbons 2 parent name 4 5 pentane 2 Number the longest chain to give the first branching point the lowest number Br Br 4 1 2 3 NOT 5 3 4 2 5 1 3 Name and number the substituents arran 39 l h b 39 39 39 339br0m0 ge in a p a et1cal order 1gnor1ng prefixes di tri tetra tert sec Z39methyl 4 Use di tri and tetra to NA designate multiple copies of same substituent 3br0m0 2 methylpentane NOT 2 methyl 3 bromopentane V 1 Solubility in Water 2 Reaction with Sodium The Hydroxyl Group Reactions of Alcohols and Phenols 39 Alcohols and phenols are organic analogs of water H OH in which one hydrogen is replaced by an aliphatic R OH group in the alcohols and by an aromatic Ar OH group in the phenols The following tesrs and experi ments illustrate some properties and reactions of alcohols and phenols Alcohols and phenols like water form strong intermolecular hydrogen bonds R R 39 Ar o H o H and o H o H The lower mlecularweigh alcohols can readily replace water molecules in the hydrogenbonded network of water H R H o H o H 0H This hydrogen bonding accounts for the solubility of many alcohols in water In this part of this experiment you will test the solubility of several alcohols in water Procedure In separate test tubes place 05 mL of each of the following alcohols ethanol lbutanol 2methyl2propanol lhexauol Cyclohexanol and ethylene glycol Add 2 ml of water to each test tube mix and observe Record your results for each alcohol on the report sheet as very soluble moderately soluble slightly soluble or insoluble Just as with water the hydrogen atom of the hydroxylgroup in alcohols and phenols can be repl ed by sodium 2 H OH ZNaaN quotquot Ig gi og H21 xedimn hydroxide X The evolution of hydrogeri39can be taken hydroxyl group or other acidic group in the metal hydroxides strong bases 2 R OH 2Na 2Na OR H21 sodium Ilkuxide evidence for the presence of a olecule Metal allcoxides like CAUTION The Lucas Te 3 St In this experiment you will observe the relative of several alcohols toward sodium tubes are c an and dry Sodium re use ofsodittm in the rink When you havemompleted all your observatl us add suf cient methanol to each tube to react completely with any unreacted sodium metal Only when all the sodiurryhas reacted may y discard the mutants of each tube in a waste hottl lxorovided by yyir instructor Procedure In separate test place 2 ml of each of the following alcohols methanol lbutanoL Zb renal and 2merhyl 2 propanoL In a fth test tube place 2 ml of be ts comparison control Using a tweezers do not diesordium metal with your ngers add an smallpieee a sphere 2 mm in diamete or a cube 2 mm on an edge of sodium metal to each tube and note the result In some cases it may be necessary to heat Be extremely careful when handling sodium Etatire that all your test I violently with water Never dig the tube over a steam bar to initiate reacci Record your results To the methanol tub only after all dioxin has dissolved add a few drops of phenolphtlg in indicator solution this dicaror is colorless in acid pink 111 base Recov your result Waste Disposal When you have nished the testska add 1 mL of methanol tipeach tube to destroy the excess sodium When no more so dium can39be observedva the contents of the tubes into a waste boule for organic solvents provided by your instructor Alcohols are classi ed as primary secondary ourtertiary depending on whether the hydroxylbearing carbon is bound to one two or three carbon atoms When treated with a particular reagent alcohols may differ in the rates at which they react or indeed even in the type of product obtained depending on the class to which they belong Tests that distinguish among the three classes can be useful in determining the structure of an unknown alcohol H H R l I R f OH R II OH R fquotOH H R R primer imdlry himquotY The Lucas reagent is a solution of zinc chloride in concentrated hydro chlon39c acid The Lucas test is based on the different rates at which primary secondary and tertiary alcohols are converted to chlorides with this reagent Zach R OH HC1 39 gt R Cl H OH The lower alcohols all dissolve in the reagent to form oxonium salts 39Ali more to be lentil should be prEViOuxly data over much are 1 CAUTION 5 Esters The Hydroryl Group u R quot 9 H H cr RCIH Cl H moxminmult The corresponding alkyl chlorides however are insoluble in the reagent Tertiary alcohols react so rapidly that it is impossibleto detect their disso lution the alkyl chloride separates immediately as a cloudy dispersion or separate layer Secondary alcohols dissolve to give a clear solution provided the R group does not have too many carbon atoms in the chain and then form alkyl chlorides cloudy solution within a few usually 4 5 minutes Primary alcohols are not converted to chlorides with this reagent at room temperature undl several hours have elapsed In this experiment you will compare the behavior of four alcohols toward the Lucas reagent Hydrochloric acid can burn Do not get Lucas reagent on your skin Procedure39 Place Zml of Lucas reagent in each of ve test tubes Test each alcohol by adding about 5 drops of the alcohol to the reagent Shake the test tube and note the length of time it takes for the mixture to become cloudy or separate into two layers Test l butanol 2butanol cyclohexanol and 2 methylZpropanol and record the results for each The fth tube containing only the reagent is used as a comparison control Alcohols react with acids to form esters H H II ROIl R39 c OH gt R39 c 0R H20 alcohol ldd ester The process is called esteri cation The producs are usually pleasant srnelling substances Ester are responsible for the flavors and fragrances of many fruits and owers In this experiment you will convert two alcohols to their acetates R39CH3 by treatment with acetic acid using an acid catalyst H1804 Procedure Place 1 ml of glacial acetic acid in each of two test tubes To one tube add 1 mL of ethanol and to the other add 1 ml of isopentyl alcohol 3methyl lbutanol Shake the tubes to effect di oluh39on While shaking cautiously add 1 ml of concentrated s acid to each tube and then place the tubes in a beaker of warm 0 C water for 5 min Pour each reaction mixture into a separate beaker containing 10 g of Crushed ice stir and cautiously smell the odor in each case Th llydroxyl Group 6 Phenols are stronger acids than alcohols or water The principal reason is that The Acidity of the negative charge in phenoxide ions Can be dclocalized into the aromatic Phenols nng through resonance whereas the negative charge in alleoxide or hydrox ide ions is localized on the oxygen atom 10 0 q p 2 2 12 5 VJ localtud chug 39 in dioxide ion Y charge deloulizuioo in pbmcrxjde ion The approximate acidity constans are 10 for ethanol 10 for water and 10391 for phenols Thus phenols can be convened to their salLs phenoxides by treatment with sodium hydroxide CAUTION Phenols are corrosive Wear gloves when working with phenols in the next three procedures If you get any phenols on your skin wash the area immediately with excess water Procedure Place 02 g or 05 ml of each of the following compounds in a Separate test tube lhexanol phenol and pchlorophenol Add 1 ml of water to each tube shake and note whether the compound dissolves Then add 2 mL of 15 sodium hydroxide solution to each tube shake again and note whether the compound now dissolves Waste Disposal Carefully neutralize the basic solution in each test tube by adding concentrated hydrochloric acid dropwise until the solution is barely acidic blue litmus turns red Withdraw the aqueous layer with a Pasteur pipet and discard it in the sink with plenty of water The remaining or ganic liquid or solid may be washed into a waste bottle for halogenated organic solvents provided by your instructor with 1 ml of acetone co Phenols and compounds with a hydroxyl group attached to an unsaturated Ream carbon atom enols give a coloration pink violet or green depending on Pb an 015 and the structure of the phenol or cool when mixed with fem39e chloride FeCl3 The Elm 15 with color is due to the formation of coordination complexes with the iron Ordi Femc Chloride nary alcohols do not react This test can be used to distinguish most phenols from alcohols Procedure In four separate test tubes dissolve one or two crystals or 1 or 2 drops of phenol resortinol 24pentanodioneand 2pmpanol in 5 ml of water In a fth test tube place 5 ml of water as a comparison control 39l39o each test tube add 1 or 2 drops of 1 ferric chloride solution shake and observe and record the results 4 The Hydroxyl Group Solubility in Water Reaction with Sodium The Lucas Test NW SECTION Report C mound Structure Emma lBuunol 2M ethylZp39m39paml 1 chanol Cyclohcxmol Ethylcnc glycol Compound Structure 39 Mammal 1 Bumnol 2Butznol 2Mcrhyl2 propmol H um annual Addition of phenolphrhalcin to the methanol solution DATE Solubilixy in warra 0 bscrvarion Compound Structure lBuumol 2B umol Cyclohexmol ZMclhyl Zp mpmol Como Tbncfor Reaction HM Esters thznnl Isopcnryl alcohol Solubility C mom Strum Walg NaOH Solution 11151on Acidity of Phenols thol p G omphmol Compound Sanctum Rand Reac on of P115091 Phenols and Ends W1 th Rcsmcmol Fen ic Chloride 24Panmtdionc i 2Prcpmol Control 2116550175 1 What general conclusions can you about the solubility of alcohols in watcr on 11 basis of your results in Sec 1 2 Which is less soluble in want 1pcntanol or lhcptanol Explain 3 Write an equation for thc maction of mcthanol with sodium 4 What cxpc mcutal cvidcncc did you obscrvo for tho products of the roac cion of methanol with sodium 5 What would you expect to happen if sodium methoxide were added to watcr Writ the equation 6 Write anoquation for the roactiou of 2 butanol with the Lucas reagcm 7 What would b the rosult of mating each of tho following compounds with the Lucas reagent Explain a 2Methyl lpropanol b Cyclopcntanol c lMcthylcyclopcntanol v 9 Describe the odor of the product derived from mixing isopentyll alcohol and acetic acid Sec 5 and write the equation for its formation 10 Write an equation that explains the solubiJj 7 of m sodmm hydroxida r3 15quotc Ompheuol m 15 11 From the results ofthis expelimam would you say that 1hexanol is more acidic or less acidic than phenol Explain 12 Write an equation for the eqt libximn between 24pemanedione and its major enolie form 13 Using tests performed in Lhis experiment ieu how you would distinguish between the members 0f each of m following pairs of compounds Give equations when appmpriaie a 1Pmpanol and 2pmpanoi b 4 Chlorophenol and 4chlorocyclohexanoi c lButanol and 2methy12propanol d 24 Pcmanedione and 2 pentanone Chapter 7 Synthetic Reactions 1 Substitution Reactions via SN1 or SN2 Mechanisms In General where Flmolecule and LG leaving group FlLG QDH R OH alcohol RG GNRZ FlNR2S amine 9 FlOFl ether 9 OR gt NR3 FlNR3 ammonium ion 68H RSH tthI eCN gt FlCN cyanides SR RSR sulfide 9N3 FlN3 azides Fl S 9 2 gt RSRg sulfonium Ion X halide FlX alkyl halides NH2 RNHg 1 amine 9H FlH hydrocarbons G o NHR RNHR 2 amine R R R acetylide ion acetylenes 2 Elimination reactions via E1 or E2 mechanisms Elimination reactions are always in competition with substitution reactions If the nucleophile is sterically hindered then it will act as a base and the elimination reaction is favored 2a Alkenes made from alkyl halides via elimination H B gt6 gt gt examples of Substitution and elimation reactions you should be able to draw the mechanisms l Aoe NED gt 0Y Nal W ANHQUCB LiCl Cl SH S HBr X O WOTsANJ WAmk G K K OTs Functional Groups Note For the quotGeneral Structure of the Functional Groupsll listed here some bonds may be connected to an quotFlquot group For the sake of learning these functional groups think of Ft an alkyl group such as CH3 methyl However the quotFtquot group can be a part of a bigger molecule We are only interested in the functional group For example Look at the methylene group listed under quotSaturated Hydrocarbonsquot In the molecule shown below at left the methylene funtional group can be drawn in a generalized manner as Methylene group H H H I I l O 9 9 H 392 R9R GeneralizedStructure H H H General Class General Structure of name of functional group Functionai Group Saturated Hydrocarbons H 1 1 I 1Akane RH ex H Q H and H399399H H H H methane ethane 39 2 Methyl HQFi 0r H3CFl or MeR H 39 8 Methylene R9R or RCH239R H 39 4 Methine RQR DJ E 0 C9 5 Cycloalkane Unsaturated Hydrocarbons 1 Alkene R R double bond C Q Fl Fl Fl Fl 2 Allene ICCC Fl Fl Fl Fl 8 Conjugated Alkene CC R Ft B I Czc or 00 s I R Fl any pi system 4 Alkyne Triple Bond R 00 R Aromatic Benzenoid Hydrocarbon H 1 benzene H l H 5 5 0 0 H 9 H H R 2 Phenyl O or PhR or CeH5R R 8 Aryl R39 or Ar39R RI any substitution on the phenyl ring R Note The term quotArylquot is a broad term and can include any compounds that exhibit aromaticity including the phenyl functional group I For Example this pyridine ring can be classified as an quotArylquot group N Hydroxy Compounds 1 Primary Alcohol 39739 F39 39 7 Hydrate RCOH H d 10 R O OH I y roxy H dlol OH H 2 Secondary Alcohol R OH R R O I Hydroxw39 2 39 8 Halohydrin X Q Q39OH R R R 8 Tertiary Alcohol R OH where x F Cl Br I Hydroxy 8 CIDH Rbcl R 9 Cyanohydrin RCCN I 4 Allylic Alcohol R C OH R I R R R 10 Enol gtlt Flt vinyl alcohol H OH ArCOH 5 Benzylic Alcohol 11 Phenol ArOH R R 6 Glycol Ho OH diol I I R R 12 Peroxide ROOH Ethers FiOFi Fi Q In 39 5 1 EpOXIde Icc 5 Hemiacetal R q o R a onho ester R o 9 o R R H 0H OR Fi R R 2 Enolether cc RI OR 6 Ketal R OR 9 Dialkyl perOXIde FiOOFi OR Fi lOFi 8 Ketene acetal lcc Fli H 0H 7 Hemiketal RQOR H 39i 4 Acetal R gOR OR Halides quotXquot where X F Cl Br I R X H I 9 Aryl Halide 1 Primary Halide R x 5 Benn Hams Ar 9 X 1 139 R H 6 Vicinal Dihalide gtlt gt5 10 A IH Id 9 o ai e 2 Secondary Halide R x R 9 9 H y R C X 2o R R 8 Tertiary Halide R x 7 Geminal Dihalide R x 8 ii i R R 4 Allylic Halide CC R 8 Vinyl Halide CCIR FI 9Igtlt R X R Amines NRa H 1 Primary Amine R39l 539 Hydrazme 39NNH2 I H H 6 Enamine Fi R 2 Secondary Amine R39 vinyi amine lcc I 39 R NR R F39i F R 8 Tertiary Amine PEN 7 Amine Oxide R39 O ii 39 4 Quaternary Amine R E R X 8 I Fi mine Pg Schiff39s base gtNR Carbonyl Compounds O O 11 Peracid quot 1 Aldehyde a or RCHO C OOH R H O 0 ll 2 Ketone a 12 Acy Peroxide RCOOCR II R R O R 9 8 Ketene CCO 18 L t amp CtNH R ac am cyclic amide H20 NR 4 Quinone oltgto for example 9 9 5 Carboxylic Acid C 14 39factope H CCO C o RCOH or RCOZH cyc ic es er 2 n O for example 6 ESter amp or RCOgR Fl F3 R OR 15 Imide O N O N 7 Perester 9C kw R OOR a for example 0 16 Carbamic Acid R 9 39 ll a 8 Amide 0 R N OH N R I R O O 17 Carbamate R C 9 39 39 Urethane c 19 Carbonate I 9 Diacylamide amp E N OR RO C OR R N R 39 I Ft H O o 20 Haloformate L o o 18 Urea II RO X 10 Acid Anhydride H H RN CN R RCOCR I I H H Carbonyl Derivatives Note All of these groups can be prepared from carbonyl compounds and can hydrolyzed back to carbonyl compounds OH 4 Acetal 1 OXIme CzN39 5 Ketal H H R 6 Hemiacetal see Ethers 7 Enolether R H R 2 H drazone 39 y CN 8 39m39ne See Amines R 9 Enamine H 10 Enolate See Salts 8 Semicarbazone R N NH2 cii39 c 11 Enoi 12 Cyanohydrin see AICOhOIS Sulfur Compounds 6 DISUlfIde RS39S39R 11 Sulfonamide Ar g N39 II 1thio H314 O mercaptan 7 Sulfoxide 8 or C 9 s 2 Thiophenol ArSH Ft Ft R R 12Su39fonate R f 0 R S 9 91 9 8Thioaldehyde 5 8SU39f0ne RSR or RSR 18Sulfonlehloride Ar S CI II I R H o o o S 14 Thio Ester quot 4 Thioketone amp 9 Sulfonlum Salt See Salts 39 RICSR R 10Sf 39A39d 9 RUSHR 5 Sulfide FtSFt 39 uon39c 639 R OH 15 Episulfide c Q o Phosphorus Compounds O 1 Phosphine Rap 4 Phosphonate R3939OR 6 Phosphonium Salt See Salts I OR 2 Phosphlte FtOPOFt 7 Phosphorane CIDFt 0 Phosphorus Ylide o 5 Phosphate Ft OlgOH R R II I I 8 Phosphlne OXIde R R oR Arapq or Ar3PC R R Salts 1 Carbocation I Ft 039 H Carbonium ion R A 7 Enolate 100 Fl Ft Ft 5 2 Carbanion R c39 H 8 Thiolate FtS H Flt F O 9 o 39 39 8 Carboxylate amp xomum R 9 A R o H R 4 Alk d R O H 10 Diazonium ArN2 A or Ar NEN A OXI e Ph d Ar 0 H 11Sulfonium Ft3S A39 5 enoxi e 12 Phosphonium F4393 A 6 Ammonium R Kj H X I R Organometallic Compounds 1 Grignard FlMgX 5 Dialkylborane RgBH 2 Alkyllithium RLi 6 Silane SiH4 R3SiH 3 CUPrate LiCURz 0r MQCUsz 7 Dialkylmercury FlHg Fl H 4 Diborane BgHe 0r B H H Miscellaneous Groups 39 39 1Nitrile RCEN BAZide R NZNZN RNNEN lt gt RN NN cyanides or Fl CN F o 9 Carbon Radical R G charge is zero 2 Nitro Q or RN02 R R o 10 Cyanate R o CEN NH 339 Nitroso RNO 14 Amidine amp R R R N 4 A20 FlNNFl 11 Cyanamide NCEN R R W R NH 5 Ozonide RjC CC I I NH 15 lmldo ester H R Fl 0 12 Guanldlne F0 0 c B RN N 639 lsocyanate RNCO R R 16 Imido chloride 1 0 7 Isothiocyanate R NCS 18 Carbodiimide R NcN R R Cl Multiple Functional Groups Combined to Give a New Group 1 Aldol 9H 9 CQC 5 Rf C R 4 Amino Acid He 0 OH R R 39l O H O 2 a SUnsaturated Ketone Fl Ia cc R I x O O R 5 O H II II 5 betaKeto Ester clt1c R 5 C OR R R NR2 o 8 Mannich Base RE 1 Fl v R RR


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