Week 1 Reading/Lecture Notes
Week 1 Reading/Lecture Notes CHEM 2321
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This 6 page Class Notes was uploaded by Hayley Lecker on Friday August 28, 2015. The Class Notes belongs to CHEM 2321 at University of Texas at El Paso taught by Dr. James Salvador in Fall 2015. Since its upload, it has received 243 views. For similar materials see Organic Chemistry I in Chemistry at University of Texas at El Paso.
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Great in-depth overview!
Well written notes that go above and beyond what the lectures actually cover. Would definitely say anyone taking O-chem should get these. SHould get an A with these notes.
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Date Created: 08/28/15
Organic Chemistry Week 1 Important Information Professor s Email isalutepedu Class Website organicutepeducourses2324 Class Code Ebook utep232Xfall2015 Chapter 1 is a review of Gen Chem 1 amp 2 so notes will not be included 2425 Normal or nAlkanes reference pages 7981 systematic approach to naming of chemical compounds did not begin until near the end of the nineteenth century Still many compounds are called by their quotcommon names UPAC Fundamental rule of chemical nomenclature each different compound must have a unique name Straight chain alkane rules Alkane means fully saturated meaning no double or triple bonds only single 1 The prefix will indicate the number of carbons in the group Example A 5carbon chain starts with pent CH3CH2CH2CH2CH3 You may also see the skeletal structure which looks like Each point is a carbon if you count left to write there is 5 points this includes the ends as they are carbon points M as well 2 Adding the ending ane So A 5carbon chain is pentane ane is used for fully saturated carbon chains Quick Chart try to memorize up to 12 carbon atoms Name Number of Structure Carbon Atoms Methane 1 CH4 Ethane 2 CH3CH3 Propane 3 CH3CH2CH3 Butane 4 CH3CH2CH2CH3 Pentane 5 CH3CH2CH2CH2CH3 Hexane 6 CH3CH24CH3 l Heptane CH3CH25CH3 Octane 8 CH3CH26CH3 Nonane 9 CH3CH27CH3 Decane 10 CH3CH28CH3 Undecane 11 CH3CH29CH3 Dodecane 12 CH3CH210CH3 Tridecane 13 CH3CH211CH3 Tetradecane 14 CH3CH212CH3 Pentadecane 15 CH3CH213CH3 Hexadecane 16 CH3CH214CH3 Heptadecane 17 CH3CH215CH3 Octadecane 18 CH3CH216CH3 Nonadecane 19 CH3CH217CH3 Eicosane 20 CH3CH218CH3 Heneicosane 21 CH3CH219CH3 Doeicosane 22 CH3CH220CH3 Trieicosane 23 CH3CH221CH3 Triacontane 30 CH3CH228CH3 Hentriacontane 31 CH3CH229CH3 Dotriacontane 32 CH3CH230CH3 Tritriacontane 33 CH3CH231CH3 Tetracontane 4O CH3CH238CH3 2123 ISO and Neo Common Names reference pages 7279 21 Drawing Organic Structures IUPAC stands for The International Union of Pure and Applied Chemistry it was started in 1889 Hydrocarbons are the backbone of all organic compounds Since molecules are 3D and structure determines properties visual representations have been created Type of Visual Representation of molecules 1 Two dimensional structural formula Example pentane C5H12 H H H H H H H H H H 2 Condensed structural formula Example pentane C5H12 CH3CH2CH2CH2CH3 To condense more take out the lines connecting the carbons CH3CH2CH2CH2CH3 Now even further condensed combine repeating methylene groups CH2 CH3CH23CH3 3 Bondline structural formula referred earlier in notes as skeletal structure Ends and points represent carbons the CH bond is not shown For hydrocarbon rings things might become cluttered so using bondline structure is best Example H R If H 39 A 3quot Ha x x I IH ft fr at H a H E rH H I f H M nfl i39 l p H H H ZMH Iyl n op me EH EH2 a As you can see the three structures are represented in the images CHE CH Methylcyrclllopentme 22 Alkanes Alkanes are the simplest hydrocarbons they form sp3 hybridized bonds That simple means each carbon makes 5 bonds Thus alkanes are saturated hydrocarbons There are two categories of saturated hydrocarbons alkanes and cycloalkanes To figure out the number of hydrogen s in an alkane use the formula CnH2n2 To figure out the number of hydrogen s in a cycloalkane use the formula CnHZn Example pentane would be C5H12 while cyclopentane would be C5Hlo 23 Structural lsomerism Molecules may contain up to 3 hydrocarbons before having another structure Example C4H10 EH23EH3CHZEEH3 HgCHEHZg tle Compounds with the same molecular formula but different structures are isomers As the number of carbons increases after 3 the number of isomers increases as well There are two categories of isomers stereoisomers and constitutional isomers Stereoisomers bond in the same order but differ in 3D arrangement Constitutional isomers same atoms but bond differently Note during the homework you may have seen neo and iso being used Neo is used for when there is one carbon in the hydrocarbon connected to 4 other carbons Iso is shown above 27 Common Names of Alkvl Radicals reference pages 9095 To name some of the simplier of these complex chains use prefixes n iso sec and tert These prefixes are not part of the IUPAC system Steps for naming complex alkyl groups 1 Use IUPAC system to name rest of compound and to determine position of alkyl group 2 Count number of carbons in complex alkyl group to name and use appropriate prefix a Prefix n E ai i w i Use to name a straight chain isomer that contains 3 or more carbons Example npropyl CHgEHEEHE b Prefix iso gm i Indicates a structure in which 2 methyl groups are bonded to the end of EH3 an alkyl side chain farthest from the point where the side chain bounds to CHECHIEHEJH the parent chain Example isopropyl EH23 c Prefix sec MECH E ai n Emu i Indicates structure in which the carbon that bonds to the alkyl side chain to the parent chain bears a methyl branch Makes that carbon a econdark carbon Example secbutyl 113 Note exception to this prefix is secpropyl CHSEHE39CH always called isopropyl d Prefix tert sec Entry gmup EH3 i Structure where the carbon that bounds the alkyl side chain to the parent EHEEEHEJH IJ chain has two methyl branches making the carbon tertiary Example tert CH3 butyl CHEE EH3 fewEmmi 3 Write name of compound in the following manner prefixalkylalkane CH3 I39m Example Ll Dimlrljrlllethyl 27 pages 9597 contain practice problems Lecture Notes for the Week Methane CH4 Methyl CH3 Methylene CH2 Methine CH If one carbon is bonded to another carbon it is called primary or 1st degree If two carbons are bonded to a center carbon it is called secondary or 2ncl degree If three carbons are bonded to a center carbon it is called tertiary or 3IrOI degree If four carbons are bonded to a center carbon it is called quaternary or 4th degree Count the carbons around the center atom NOT the bonds a carbon can be surrounded by two carbons but be doubled bonded to one and single to another so do not count the bonds count the carbons nclass responses have been based off the following image Mifepristone 1St line between carbons is called a sigma bond one line 239 line between carbons is called a pi bond two lines For every sigma bond there is an antisigma bond and for every pi bond there is an antipi bond Molecular Geometry View next page for chart Molecular Geometry table inserted for explanation Electron and 1A39Iolecular Geometry On Central Atom Electron Regionsamp Bonding Lone Electron Region Molecular hybridization Regions Pairs Geometry Geometryr hmples 2 2 0 linear linear Belquot2amp0 I Be II 5 p 1 1 lmear 00212 co 3 quot o tri al 1an gm BF co 2 F gon p ar planar 3 3 FB 1 39 I F sp 6 0 2 1 bent 03 so2 0 6 1 2 linear 02 20 t1 l 4 o tetrahedral tetrahedral 144804 15 D f quot H Sp H I H 3 1 my mtH0 Her0quot pyramidal J J H 2 2 bent no 101 quoto H If H l 3 linear HF OH H 3 5 tri a1 tri a1 a on gon 00 3 o g PF P sped blpyramidal blpyramldal gt SF eTeCle Fit 4 1 seesaw 4 4 1 St E4 oFo F F 3 2 Tshaped 13 2 cl 2 3 linear 131Xe12 I I 1 6 PF6 QF JJIF 6 0 octahedral octahedral 3 sp cl2 3116 F F 90 00 39 I i a 1531 5 1 Square 35 F IquotB39Hr pyramidal Shelf 3 square F ml 36quotquot 5ltt39 4 r Xe 39 quot planar 439 4 IFquotquot3
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