Chapter 2 notes - Spring semester 2014 PDF

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Spring semester 2014...

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BeginChapter2–TheNatureofOrganicMolecules.Printthesenotesbeforelectureasyouwillbefillingintheblank boxesinclass. 1. FunctionalGroups,awayofcategorizingorganicmoleculeswithsimilarreactivity(likepKa). a. listoffunctionalgroupexamples(table2.1intext) alkane



nitrile



alkene



nitro



alkyne



aldehyde



arene



ketone



halide



carboxylic acid



alcohol



carboxylic acidchloride



ether



ester



amine



amide





b. FunctionalGroupswithC‐Cbonds     c. FunctionalGroupswithpolarsinglebonds     d. FunctionalGroupswithpolarbonds     2. Alkanes–saturatedhydrocarbons,oftencalledaliphatic a. greasy,non‐reactive,non‐polar,allsp3hybridized b. foundasgases,liquids,andwaxes c. branchedchain,cyclicandacyclic 3. Nomenclature(section2.2to2.3) a. Twosystemsofnomenclature,IUPAC(InternationalUnionofPureandAppliedChemistryandthe “common”nomenclaturesystem i. example,2‐(4‐isobutylphenyl)propanoicacid    ii. hexanevscyclohexane   







3‐methylhexane 

2,2‐dimethylpropane 

4‐ethyl‐3‐methylheptane 

4‐ethyl‐3‐methylheptane 

n‐butane

isobutane

b. Carbonstructuralclassification,methyl,primary,secondary,tertiary,andquaternary. 









methyl asalkylhalide

primary 

secondary 

tertiary 

quaternary 

 4. Substituentnomenclature a. Tert‐butyl,isobutyl,isopropyl,(fulllistonweb)   5. Isomers a. Constitutional–samemolecularformula,differentorderofconnectivity(samefunctionalgroup) i. Butane,isobutene   b. Differentfunctionalgroups i. Ethanolvsdimethylether  6. Intermolecularattractiveforces a. trendsinboiling/meltingpointsasafunctionofsurfacearea

https://en.wikipedia.org/wiki/File:AlkaneBoilingMeltingPoint.png



7.

8.

9.

10.

11.



b. vanderWaalsinteractions(non‐covalent,non‐electrostatic)  Conformationalanalysis a. ethane b. sawhorseprojection,Newmanprojection(staggered/eclipsed) c. butane,Newmanprojection(anti,eclipsed,gauche) d. Dihedralangleplotsofpotentialenergyforethane Cyclicalkanes a. Cyclopropane,cyclobutane,cyclopentane,cyclohexane b. Ringstrain c. 5‐and6‐memberringsarenotstrained Cyclohexane a. Chairconformation(buildmodel) b. axialandequatorialpositions,howtodraw c. ringflip Monosubstitutedcyclohexane a. Nomenclature&howtodraw.Ex.Methylcyclohexane b. Lowestenergychairconformation Disubstitutedcyclohexanes a. Nomenclature b. cis&trans1,2‐dimethylcyclohexane c. cis&trans1,3‐dimethylcyclohexane d. cis&trans1,4‐dimethylcyclohexane 

SomeProblems: 1. HowmanyconstitutionalisomersaretherewiththeformulaC3 H8O?Drawthem.  2. Writeasmanystructuresasyoucanthatfitthefollowingdescriptions: (a)AlcoholswithformulaC 4H10O(b)AmineswithformulaC 5 H13N (c)KetoneswithformulaC 5H10O(d)AldehydeswithformulaC5 H10O (e)EtherswithformulaC 4H10O(f)EsterswithformulaC 4 H8 O2   3. Thefollowingnamesareincorrect.Drawthestructuresrepresented,andgivetheproperIUPACnames. (a)2,2‐Dimethyl‐6‐ethylheptane(b)4‐Ethyl‐5,5‐dimethylpentane (c)3‐Ethyl‐4,4‐dimethylhexane(d)5,5,6‐Trimethyloctane  4. SightingalongtheC2‐C3bondof2‐methylbutane,therearetwodifferentstaggeredconformations.Drawthem bothinNewmanprojections,tellwhichismorestable,andexplainyourchoice.   5. Theso‐calledstatindrugs,suchassimvastatin(Zocor),pravastatin(Pravachol),andatorvastatin(Lipitor)arethe mostwidelyprescribeddrugsintheworld,withannualsalesestimatedatapproximately$15billion.         (a)Identifythefunctionalgroups(oralkylgroups)labeledA–I. (b)ArethegroupsCandEonPravacholcisortrans? (c)Whycan’tgroupsG,H,andIbeidentifiedascisortrans? ...