Exam 2 Study Guide- Organic Chemistry
Exam 2 Study Guide- Organic Chemistry 333
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This 8 page Study Guide was uploaded by Courtney Patterson on Wednesday October 21, 2015. The Study Guide belongs to 333 at University of South Carolina taught by Leslie Lovelace in Fall 2015. Since its upload, it has received 200 views. For similar materials see Organic Chemistry I in Chemistry at University of South Carolina.
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Date Created: 10/21/15
Organic Chemistry Exam Study Guide 2 i 39 Alkanes so3 and have 1095 bond angles a To calculate number of hydrogens CnH2n2 3 a m it H a H i ii I ro a EhoLm P a n Mt ankng I Constitutional isomers o n butane L Cohs mow l g a 9 v l lsDWIS e l 1 g o npentane i Q or 1 g g 39 g 5 Same I I39UP AC Rules for Nomenclature o Unbranched molecules I Number of Cartoons ane I Example npentane o Branched I Longest chain is the parent chain Example Heotane ff 7 n n 3919 ho rmcu S a a tf hi n p an mm e 3 n hut MC 39 n a crane jail w non 0316 n a more 339 Q h Gent 639 carom 3 Jquot LO n gt 1 aw 3 Identify snub sti ruen ts and street address I Chen5e the newest number possible for substituents 391 Exa mrpl39e dimethy heptane 3 r E a Q 393 2 e b e 391 3 T e 1 Common subsrzituren ts q a 3 r 3 Merrhy 1me e e I l quot E 1 ft 1 i a 1 a I quot CW new Q in F g 0 n r o 2 or more Eldrentica substituents 1 5 quot 2 C i 39 3e tri Lt I 4 te tra quotb l 5 penta I Example 23 dimethyl hexane o 2 Or more different substituents 39 List alphabetieellly I Lowest possible numbering Example 4ethyl3methy heptane NI Jquot quotII 0 Di tri tetra prefixes are not included in alphabetical orders I D i methyl 39 Emmi I But iso loolc at the V I Example 2 methyl 3 ethyl56dipropvl nonane i i a o 9 3 I L g o quot z a 5 1 39l 1 i 3 g a as H Li lug E as 0 Choose Chain with most substituents I Choose chain with sobstituents that are easily narnahle I 3secbuty l2257tetramethyl decane 9 i1 3 i559quot q I D 15 i Classification 3f carbons o 1quot1 attached to one other carbon 0 2390 attachetil to two other cartoons 0 30 attaohedi to three other carbons o 40 attachedi to four other carbons a Cycloaikanes o Cyclopropane w I Scarbons o a o Cyclobuitane 3 g I le arbons 7 a o o Cyclopentane u n I 5 carbons 139 o Cyelohexane 3 it I anrbons 9 a Q o If only one substituents no numbering if mo re than one number carbons 0 Example 1methyi 34 di etln39yli hexane E i S 1 5H I BicycllcCornpounds o Fused rings Example Blewle 4413 decane aquot3 Iquot i 1 t 39 a 7 1 t Lquot l H L We 0 Bridged rings 01 390 Number around larger ring rst Bxieyleo 321 octane l 1 i l 1 a g 395 iquot J a W1 392 I 5 o Specify allltene by either a double bond starts onj nurnber of carbonsene or nurnber of carbons 12 double bond starts onlene o Example 45dimethyl Eheaxne or 45 dlmetnylnex2ene I Alkemes o Doublebond 1 I 3 as E s 3 a Alkyl Halides o llalllde comes rst 0 Chloro bromo 0 Example 2bromo3 lidimethyl fleptane 3r a a 6 a a z c Q L to l 3 5 1 so Alcohols 0 Number carbon alcohol ls attached to number of carbons ol o Example24methyl 39apenlanol 3 L1 2 o e aw re 3quot o q a l 5 5 Cg EJ Alkvnes 0 Either llt triple laond starts drillnumber of ca rbons yne or number of ca rbonsa tr triple bond starts onjllV ne 0 Example 3 neX yne a 5 O Newman prolection o Energy of butane eelrpsed 13M 3 t 3 a J39 39 infgala 5l39lwmhill i 39 quot quott quot quot39 tm E that l9 I s I 9 am w 39m 39 m 39i a a es 1 lane t vew an 2 4 o e so 39 Jeri Drheorai angle Strains o Steric strain nonlbonded atoms separated by 4 or nglore bonds they are forced closer than the atomic radii allowr 7 FE 39 l lfl39 it H Angle strain bond angle is compressed or expanded from optimal not quot ix 0 or H o Torsional stra39in When rotating a molecule around a bond the torsional strain i5 the repulsion caused by the electrons in between different groups when theirr pass by each other o Cycloalkanesstraih l4 39 Cyclopropazne i b E 5P3 a loalSF i o tooquot 12 ol0 0631ch 39 a Cyclobutane j 39139 Potifs of ii as tel 9525 1 5 394 b b H r39OT o mad Wain It 3 if H II 7V 7 5 H fe 39 Cyclopentane a a I 0339 H or a o fa 3 ratio Les 5mm 39 Cyclohexane a 39 105 i 99 of all hexanes are in chair H 39 H Mitt tree ii i iiiit 39 treat emu or r 33 lice iiirn I to aim ea iiirm Axial quot Equatorial If Elk Axial becomes equatorial when flipped H I r CH3 on cyclolhexane Ll llt tam cm H Ema 39 u a 9 m l0 U46 j u 1quot as i ii k 7 f a a a Aquot h3th Ema ng quot gt 39 139 mar J r Iquot f H u 3 quot I Multiple Subst uents prefer equatorial Ii 0 Cis same direction 0 Trans different direction 0000 It I p 5 cf 5 00000 O O C1000 O O D 12 cis 1 axial and one equatorial 12 trans both axial or equatorial 13 cis hoth axial or equatorial 13 trans 1 axial and one equatorial 14 cis 1 axial and one equatorial 14 transboth axial or equatorial I Stereochemistry Ste reoisomers Same molecular formula same connectivity different spatial arrangement Achiral superimposahle Chiral non superimposable Ste reoce nter Chirality handedness of molecules if means chiral Decreasing Priority Assign priority to groups attached to the chirality carbon I lligher atomic number 2 higher priority Look at the center carbon with the lowest priority atom facing behind it Sta rt with priority 1 and got in a circle to 2 priority to 3 priority I ClockwiseR 0 Counterclockwise If there is a tie between the groups attached go to atoms attached to those atoms Double and triple hands 6 Double x2 atoms Triplie x3 atoms Bigger doesn t always mean higher priority E nanHO MET S Ca rhoxyiic acid Ester Amide r 7 a Nitrile 7 Ear 1 I r t Aldehyde 5 E It i Keytone 637 1 H la I Alcohol gt 39 at J Amine ag F I V Alkyne 39 g f quotquot Alkiene Alkane R Enantiomers chiral molecules that are mirror images and are non superimposahle o Chiral center atom with 4 different groups attached to it 2 2 of stereoisomers nzr39t of stereocenters Diastereomers are a type of a stereoisomer occurs when two or more stereoisomers of a compound have different configurations at one or more but not alii of the equivaient reiated SEEI EOCENEFS and are not mirror images of ea i other 3 i O of as tcrco j s 6 m f m c5 fastquotUte mdS a a i p I o q a i o C i If CI o Mesocomoound 2 or more stereocenters but achirai o e U a I l 3A 0 5 i o H I i a l 3 139 Q l 0 Cyclic molecglies with 2 stereocemers 2139 4 Iquot P i o rquot 33 39 0H 391 OH to a C 3 ff 3 5 H316 a 1 I g ow OFH 3 J R g I i If a a 7 139 3 gm F o i 393 or 139 139 0 Fisher projections 55 S I I Vertical bonds are away from you 1 I Hor39izontall bonds are towards you B rquot f 5 q 3r H g i J Er r a f39 j 39 a n7 9 a g gt i g f H B r Q in e Br 0 1139 D GHQ H 0 5 N H 0 quota r 0H 17gt quot 0 it 3 g c lo CHZDa
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