Organic Chemistry I
Organic Chemistry I CHEM 2010
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Date Created: 10/11/15
3 Organic Compounds Alkanes and Cycloalkanes Based on McMurry s Organic Chemistry 6th edition Chapter 3 I Families of Organic Compounds Organic compounds can be grouped into families by their common structural features We shall survey the nature of the compounds in a tour of the families in this course This chapter deals with alkanes compounds that contain only carbons and hydrogens all connected exclusively by single bonds 31 Functional Groups Functional group collection of atoms at a site within a molecule with a common bonding pattern I The group reacts in a typical way generally independent of the rest of the molecule For example the double bonds in simple and complex alkenes react with bromine in the same way See Figure 31 Double bond CH3 H C C H20 CH2 H H H20 1 51 C C C CH 3 H H H30 I I Ethylene Menthene Bra 1312 E 3mm ine added here B B 39 x f C C k f s H H H H 31ch CH2 H20 031 0 CHa H30 H mmmm39 moks Gale Double Bond as Functional Group OH CH3 H P C H H Reaction site p Double bond Survey of Functional Groups Table 31 lists a wide variety of functional groups that you should recognize As you learn about them in each chapter it will be easier to recognize them The functional groups affect the reactions structure and physical properties of every compound in which they occur Types of Functional Groups Multiple Carbon Carbon Bonds Akenes have a 00 double bond Alkynes have a 00 triple bond Arenes or aromatic hydrocarbons have special bonds that are represented as alternating single and double C C bonds in a sixmembered ring Multiple Carbon Carbon Bonds C C Arene aromatic ring Functional Groups with Carbon Singly Bonded to an Electronegative Atom Alky halide C bonded to halogen CX Alcohol C bonded O of a hydroxyl group C39l li j OH Ether Two C s bonded to the same 0 C I IEIO39I IEI C Amine C bonded to N C39l li jN Thiol C bonded to SH group C39l li jSH Sul de Two C s bonded to same 8 C39I IEIS39I IEIC Bonds are polar with partial positive charge on C 5 and partial negative charge 5 on electronegative atom Alkyl halide Alcohol Ether Amine 2004 Thomson Brooks oole Groups with a Carbon Oxygen Double Bond Carbonyl Groups Aldehyde one hydrogen bonded to CO Ketone two C s bonded to the CO Carboxyic acid OH bonded to the CO Ester CO bonded to the CO Amide CN bonded to the CO Acid chloride Cl bonded to the CO Carbonyl C has partial positive charge 8 Carbonyl O has partial negative charge 8 8 5 H C H C C HHH H Acetone a typical carbonyl compound 2004 Thomson BrookSICole O 0 O O O 0 II II II II II II C C I I I 1 I I I l Carboxylic acid Ester Amide Acid chloride Aldehyde Ketone 2004 Thomson BrooksCole Problem 31 Identify the Functional Groups 3 H b III 3 N c c O NH2 g OH 2004 Thomson BrooksCole 32 Alkanes and Alkane Isomers Alkanes Compounds with 00 single bonds and 0H bonds only no functional groups n The formula for an alkane with no rings acyclic must be CmH2n2 where the number of C s is n Alkanes are saturated with hydrogen no more can be added They are also called aliphatic compounds IiI 111 I Ill If I If H H H H C H II ll j H H I f C I H H ll C C C H and soon H H H H H H H HH Methane Ethane Propane Butane Thomson Brooks Cole A saturated fat glyceryl stearate ll CH200CH2CH20H2CH20HZCHZCHZCHZCH2CHZCH2CH20HZCHZCHZCH20H3 0 ll CHOCCHZCchHZCchH2CHZCH2CH20HZCH2CHZCHZCHzCHZCH20H20H3 1 CHZOCCHZCHZCHZCHZCHZCHZCH20H2CHZCHzcHZCHZCH20HZCH20H2CH3 A typical animal fat 2004 Thomson BrooksCole I Alkane Isomers CH4 methane Csz ethane C3H8 propane The molecular formula of an alkane with more than three carbons can give more than one structure C4 butane butane and isobutane C5 pentane pentane 2 methylbutane isopentane and 22 dimethylpropane neopentane Methane ethane amp propane 5 H H Cll H H C C C H 1391 139 I39i 1391 Methane CH4 Ethane Csz Propane 03113 2004 Thomson BrooksCole Butanes C 4H10 C4139110 2004 Thomson Brooks0019 H C C C H HHH Isobutane 2Methylpropane Pentanes C 5H1 2z CSHM H lz H II C H H H H H H H H H 1 H H IJ C C C C H H ll ll C ll H H IJ C C H H A H I 1 1391 1 1 1 l H H C H 12 Pentnne 2Methylbutane 23Dimethylpropnne 2004 Thomson BrooksCole Alkane lsomers TABLE 32 Number ofAlkane lsomers Number Formula of isomers C613 114 Cva CSH18 18 C9H20 35 C101 122 75 C15H32 4347 CZOH42 366319 C30H62 4111846763 2004 Thomson BrooksCole 20 Alkane Isomers Alkanes with C s connected to no more than 2 other C s are straightchain or normal alkanes Alkanes with one or more C s connected to 3 or 4 0 3 are branchedchain alkanes I Constitutional Structural Isomers Isomers that differ in how their atoms are arranged in chains are called constitutional or structural isomers Compounds other than alkanes can be constitutional isomers of one another They must have the same molecular formula to be isomers 22 Constitutional Isomets Different carbon skeletons C4H10 Different functional groups C2H60 Different position of functional groups C3H9N Thomson Brooks Cole CH3 CH3CHCH3 2Methylpropane Isobutane CH3CH20H Ethyl alcohol TH CH30HCH3 Isonronvlamine and and and CHgCHZCH20H3 Butane CH3OCH3 Dimethyl ether CH30H20H2NH2 Pronvlamine 23 Condensed Structures of Alkanes We can represent an alkane in a brief form or in many types of extended form A condensed structure does not show bonds but lists atoms such as u CH30H2CH3 propane u CH30CH3ZCH3 22 dimethylpropane H H H3C H C H 7quot c C H HH H H3O CH3 24 Condensed Structures of Alkanes H H H H H H H H l l I l H 3 3 Ij H C H CH3 CH2 CH2 CH3 CH3CHZCHZCH3 CH3CH22CH3 2004 Themnleoks Cola 25 Names of Small Hydrocarbons No of Carbons Formula Name CnH2n2 1 Methane CH 4 2 Ethane CZH6 3 Propane C3H8 4 Butane C4H1O 5 Pentane C5H12 6 Hexane C H14 7 Heptane C7H16 8 Octane CBH18 9 Nonane CQH20 1O Decane 010sz 33 Alkyl Groups Alkyl group remove one H from an alkane a part of a structure General abbreviation R for Radical an incomplete species or the rest of the molecule Name replace ane ending of alkane with yl ending a l ltTiICH3 is methyl from methane a l liTiICH2CH3 is ethyl from ethane 27 33 Alkyl Groups TABLE 34 Some StraightChain Alkyl Groups Alkane Name Alkyl group Name abbreviation CH4 Methane CH3 Methyl Me CchHg Ethane CH20H3 Ethyl Et CH30HQCH3 Propane CH2CHZCH3 Propyl Pr CH30H20H20H3 Butane CH2CHQCH2CH3 Butyl Bu CchHQCHchZCHg Pentane CHZCHZCHZCHQCH3 Pentyl or amyl 2004 Thomson BrookstoIe 28 03 CII3CIIZCH3 Propane 2W4 ThommEmoks Cola Alkyl Groups CHaCIIZCIIg Propyl and Aw CH30HCH3 Isopropyl 29 04 2004 Tl39lOll39SDnlBl39ODks Cole CHBCHZCHZCHS Butane EH3 3H30HCH3 Isobutane CH30HZCI120H2E Butyl H3 CHacHCH2 Isobutyl 4V and CHSCH20H0H3 secButyl CH3 and CH3 Cl 39gHa tertButyl 30 Types of Alkyl groups a carbon at the end of a chain primary alkyl group a carbon in the middle of a chain secondary alkyl group a carbon with three carbons attached to it tertiary alkyl group 31 Types of Alkyl groups I T R lj H R iJ H H R Primary carbon 1 0 Secondary carbon 2 0 is bonded to one is bonded to two other carbons other carbon Thomson Brooks Cole Tertiary carbon 3 0 Quaternary carbon 4 is bonded to three is bonded to four other carbons other carbons 32 Types of Alkyl groups If 1H3 CHzOH R IJ OH CH3CHCHZCH20H 0 General class of Speci c examples of primary alcohols RCH20H primary alcohols RCHZOH 2004 Thomson BrooksCole 33 Types of Hydr ogensz H Primary hydrogens CH3 H C1 H CILI3 H H H CH3CHZCIJHCH3 Secondary hydrogens CH2 II391 III 111 III A tertiary hydrogen CH 2004 Thomson BrooksCole 34 Problem 38 Primary secondary tertiary or quaternary carbons CH3 CIH3 lea a CHBCHCHZCH2CH3 b CHBCH20HCH20H3 c CHBCHCHZCCHs CH 2004 Thomson BrooksCole 35 34 Naming Alkanes IUPAC Compounds are given systematic names by a process that uses Prefix Parent Suffix t Where are the substituents How many What family carbons 2004 Thomson Brookleole 36 34 Naming Alkancs IUPAC Follows specific rules a Named as longest continuous chain of C s a Carbons in that chain are numbered in sequence a Substituents are numbered at their point of attachment 1 Compound name is one word German style a Complex substituents are named similarly 37 1 Find the Parent longest continuous carbon Chain CHZCHg CH3CH2CH2CH CH3 Named as a substituted hexane CH3 CHCH CH20H3 Named as a substituted heptane CHZCH20H3 2004 Thomson BrooksCole 38 2 Number the atoms in the Chain ICH3 23H2 CH3 3CHC4H CH2CH3 NOT 9 8 CH3IJH2 39ng CIJHZCHa NOT CH3 quot 2004 Tthso BrogksCdle 3 7 CH3 SCH2 CH3 SCH34H CH20H3 1 2 CH33H2 EH3 EHch3 3 4 5 6 7 8 9 39 9 8 CH3CH2 EH3 IIHZCH3 CH3 CHCHzCHZCH CHCHZCHB Named as a nonane 31dent1fyamp vs 54 321 Substituents On CBCH2CH3 3ethyl number the On C4 CH3 4 methyl On C7 CH3 7methyl S S e n t S 2004 Thomson BrooksCole 3H3 CH3CH2 C CHZCHCH3 Named as a hexane 6 5 4 l 3 12 1 IIII2 CH3 CH3 Substituents On C2 CH3 2methyl On C4 CH3 4methyl On C4 CH20H3 4ethyl 2004 Thomson BrooksCole 4O 4 Write the name In 2 1 9 a CH20H3 CH30H2 CH3 111ch3 EHagIECHEHggHggHa 6 5 4 a 7 6 5 4 a 2 1 3Methylhmne 3Ethyl47dimethylnonane 3Ethyl2methylhexnne 2004 Thomson BrooksCole 1 CH3 CH3 6 5 l4 3 2 1 23H2 CH3CH2 CH23HCH3 OHS 39HC4H CHZCH3 sz CH3 3H29H29H3 CH3 4Ethyl8methylheptane 4Ethyl24dimethylhexane 2004 Thomson BrooksCole 41 Practice prob 32 IUPAC name CHZCH3 CH3 l CH3CHCH2CH2CHZCHCH3 Solution 7 8 CHZCH3 EH3 26Dimethyloctane l 2004 Thomson BrooksiCole Practice prob 33 structure I 3isopropyl2 methylhexane CCCCCC Two substituents isopropyl amp methyl Add hydrogens to complete the structure Solution CH3CHCH3 CH3CIIHCHCH2CH2CH3 3Isopropyl2methylhexane CH3 1 2004 Thomson BrooksCole 45 Problem 311 IUPAC names FH3 a The three isomers of C5H12 b CHBCHZCHCHCH3 CHZCHS EH3 I3H3 c CH3ZCHCHZCHCH3 d CH33CCHZCHZCH CHZCH3 2004 Thomson BrooksCole 46 Problem 339 Draw structures 1 2 methylheptane 2 4ethyI22 dimethylhexane 3 4ethyI34dimethyloctane 4 244trimethylheptane 5 33diethyI25dimethylnonane e 4isopropyI3methylheptane 47 35 Properties of Alkancs Called paraffins low affinity compounds because they are relatively unreactive They will burn in a flame producing carbon dioxide water and heat 48 35 Properties of Alkanes They react with CI2 in the presence of light to replace H s with Cl s not easily controlled 0H4 012 CH3C1 H01 CH2C12 H01 0H013 H01 0014 H01 Thomson Brooks Cote 49 Physical Properties Boiling points and melting points increase as size of alkane increases I Forces between molecules temporary dipoles dispersion are weak 2M4 MiriamBroom OBIS Physical Properties 300 Melting point I Boiling point 200 100 Temperature YC 1 2 3 4 5 6 7 8 9 10 11 12 13 14 Number of carbons Thnmsun Brooks Cole 36 Cycloalkanes Cycloalkanes are alkanes that have carbon atoms that form a ring called alicyclic compounds Simple cycloalkanes are rings of CH2 units CH2n Or CnH2n Structure is shown as a regular polygon with the number of vertices equal to the number of C s a projection of the actual structure 36 Cycloalkanes A E Cyclopropane Cyclobutane Cyclopentane Cyclohexane 2004 Thomson 9 BrooksCole Complex Cycloalkanes Naturally occurring materials contain cycloalkane structures Examples a chrysanthemic acid cyclopropane a prostaglandins cyclopentane a steroids cyclohexanes and cyclopentane Complex Cycloalkanes Prostaglandin E1 PGEI Chrysanthemic acid Cortisone Properties of Cycloalkanes Melting points are affected by the shapes and the way that crystals pack so they do notchange uniformly 200 Melting point I Boiling point 100 Temperature C 3 4 5 6 7 8 Ring size e 2004 Thomsunl moks Cola 37 Naming Cycloalkanes Count the number of carbon atoms in the ring and the number in the largest substituent chain If the number of carbon atoms in the ring is equal to or greater than the number in the substituent the compound is named as an alkylsubstituted cycloalkane For an alkyl or halosubstituted cycloalkane start at a point of attachment as C1 and number the substituents on the ring so that the second substituent has as low a number as possible Number the substituents and write the name 1 Find the parent H4 3 carbons 4 carbons lghethylggclopentane lCyclopropylbutane 0r butylcyclopropane Number the substituents amp write the name CHa l Dimethylcyclohexnne lower SEthyIlAdimethylcycloheptane Lower Lower 2004 Thomson Brookslcme a 6 NOT 5 a 4 CH3 15Dimethylcyclohexane Higher lEthyl26dimethylcycloheptane Higher NOT 3Ethyl14 djmethylcycloheptane ngher I Examples 2 C H3 H W 1 Br lBromoZmethylcyclobutane 2004 Thomson Brookleoie Br EH3 2 6 CHCHZCHS a 5 H CH 3CH2 4 CH3 lBromo3ethyl5methyl lMethylpropylcyclobutane cyclohexane or secButylcyclobutane 2004 Thomson BrooksCole CH3 ELI Br 2Bromo1methylcyclobutane C1 CH3 2 4 3 CHQCH3 lChloro3ethyl2methyl cyclopentane 60 Problem 315 IUPAC names 3 CH3 CHZCHZCH3 C CH 3 6 CH3 f Br CHCH32 CH3 Br CCH33 2004 Thomson BrooksCole CH3 d CHZCHB 61 38 Cis Trans Isomerism in Cycloalkanes Rotation about 00 bonds in cycloalkanes is limited by the ring structure Rings have two faces and substituents are labeled as to their relative facial positions There are two different 12 dimethyl cyclopropane isomers one with the two methyls on the same side cis of the ring and one with the methyls on opposite sides trans 62 38 Cis Trans Isomerism in Cycloalkanes is391239Dim9thylcyclopmpane trans12Dimethylcyclopropane Thomson Brooks Cole 63 Stercoisomers Compounds with atoms connected in the same order but which differ in three dimensional orientation are stereoisomers The terms cis and trans should be used to speCIfy stereOIsomerIc ring structures Recall that constitutional isomers have atoms connected in different order 64 Stereoisomers Constitutional isomers CH3 different connections I between atoms CHg CH3 and Stereoisomers H3C CH3 H30 same connections and but different three H H H CHC dimensional geometry 39 Thomson Brooks Cole H H30 2 CH3 Br 5 4 H H 4 H H 2 CH2CH3 giggmls Bgghylcyclobutane trans1Bromo3ethylcyclopentane 65 Practice Prob 34 Name a H CH3 b H I x Cl H3C H 01 2004 Thomson BrooksCole 66 Problem 318 IUPAC Name a H H3O CH3 H Cl I 2004 Thomson Brooks Cole 67 Problem 349 IUPAC names a CH3 d CH3 2004 Thomson BrooksCole 68 I Problem 355 Four cis trans stereoisomers of menthol This is the natural one CH3 Menthol CH3ZCH 2004 Thomson BrooksCole 69 I Gasoline Octane Ratings CH3CHZCH20HZCHZCHZCH3 Heptane octane number 0 2004 Thomson BrooksJCole le3 CH3 CH3IJCH23HH3 CH3 224Trimethylipentane octane number 100
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