Exam 1 Study Guide- Organic Chemistry
Exam 1 Study Guide- Organic Chemistry 333
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This 6 page Study Guide was uploaded by Courtney Patterson on Saturday September 19, 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 180 views. For similar materials see Organic Chemistry I in Chemistry at University of South Carolina.
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Date Created: 09/19/15
Organic Chemistry Exam 1 Study Guide 1 Shells a Lower shells have lower energy because they are tightly packed on r 3 Lower Energy LUMH I oom m 8 Higher Energy b Electron Configuration i Fill lowest subshell before moving on ii Opposite spins paired ll l l NaLy i k 393 2 3 pr 39ZMZPE 9 Formal Charge a Number of valence electrons Number of electrons in lone pairs Number of bonds 3 Molecular Geometry and Shape a Lone pairs cause a shift in bond angles and change bonds lengths b Steric Number number of bonding groups attached to an atom bonds and lone pairs 1L 2 P721 35 7 53 Lair 395 FEE PR Geometries Stew 3 Base Geometric E lone pair 2 lone penis 1 lme pairs ail lone pairs qa 1 lone Eats 3 Max s i39 X Linens X 3 3 3 its one s E39n RJm a ktlarynx Q I39 Evianpm Phith Begun or Angular ll 3 9 s r 393 9 A i if quot31 M Ext R X W K sanse as If I ef mhegiml T wsoml Fg39rnmiaig Hem or Anglar l 1 X a 1quot g f l I 1 5 q EelE 3 34 1 3 mm lquot 939 has H 33 EdeEfj39fwg k 3933 17939 39 f Equot 39 ycsni39l39Ei x tremor533 I39 39I Eri l quot sfF a I n J X X X 1C Tajigtmni S dh il or Seesaw Hour x 7 ID 39539 1 d 5rtm ix A wxir l mQEWX mxf mtua t i EM EMHMRI gi r h Ea3 FVnFhquot39 k v 39 39 I 39I u 3 H re mg gig I 33933 73 233 5 I 34 5quot four w i r39 z 5 A P u 3 hill 1 Ocmlse rni Eqma39e Pyramid Seam Planar T silmoe Linear 4 Resonance a Shows same compound but just a different way to draw it b Rules of Resonance 5 i Same number of electrons between resonances i39i it must be a valid Lewis structure ii39L You can never move atoms iv Do not break single bonds but you can break a double down to a single or triple to single v The number of paired and unpaired electrons must remain the same c Single head and double head arrows m i Single arrows one electron is moving Double arrows two ellectrons moving d Relative Importance important factors to show which contributes more to the overall resonance i Filled octet ii Makes the max number of covalent bonds iii The least separation between opposite charges iv The negative charge is on the most electronegative atom is ill 1 393 ay 3A er i t r r at 1 1 W 3971 j I 39 Orbitals regions of space electrons travel in a Electrons are in orbitals but not defined in orbitals b We never know exactly where electrons are but we have a reasonable probability pv c Constructive adding orbitals in phase i o bonding single bond cl Deconstructivee subtracting orbitals out of phase ii or bonding antibonding I an bonding Er bonding e Molecular Orbital Energy Diagram i Atomic orbitals combine to make molecular orbitals ii The driving force for this is that molecular are lower in energyr than atomic orbitals Energy orbital a ital 2 Moieooiar orbitals 6 Hybridization a Regions of density lone pairs and all bonds Number of regions Bond Amalie HVlJrid Qrbitals s 2 39 2 Q 0 121 180 so i 120 so2 39 1095 7 so3 H k i a c 4 H P The hybridizations and bonds ofthese specified atoms I D 1 H H lquot 19 2H3 0 391 db I 1 H c gt 8 3 7 3 2 Cl 0 E SPY 3p a Cl C P T1 7 3 a SP3 SP 0 b Bond lengths i Sp3 gt so2 gt so 7 3 Character a The more 5 character the shorter the bond length but the stronger the bond 8 Drawing compounds a Dash formula H H H i l I Hquot C C ac 0 H I I n O i 1 H t1 b Condensed formula l c Bondelineuangle formula We 9 Hydrocarbons molecules ofjust Carbon and Hydrogen a Alkane i only single bonds V H b i i every carbon has max number of hydrogen b Alkene I One or more double bonds n ene I One or more triple bonds 7 ii yhe aquot quot d Aromatic i Ring of carbon and hydrogen ii Double bonds and single bonds 239 r gt c Alkvne iii cane 10 Functional groups a Aikyl halide i a i An alkane with a halide F Cl Br I a 39 c t Primarv carbon bonded to halide is only bonded to one carbon H iii Secondarv carbon bonded to halide is bonded to two carbons F 239 iv Tertiary carbon bonded to halide is bonded to three carbons 39539 Alcohols i 0H bonded to 5p3 carbon Olt E ii RoH 139 Primary HADH in Secondaryquot WTb l v Tertiary K gtlt39H c Ethers i Oxygen bonded to 2 different alkyl groups V o g 1 ii ROR 39 cl Amines i Nitrogen bonded to one two or three carbons by a single bond ii Prirnanr H E H I 739 339 iii Secondary l H quot quot39 N quotquot 5396 3 V I iv Tertiary c h C33quot quotc 395 e Aldehyde Cr 5 L i Carbonyl groupbonded to at least one bird rogen O C quot 3 f Kevtones P C A 6 s v i Carboayls added to 2 ca bon groups ll V ERc n gs Carboxviic acid i ECODJA group iigE0H X Ester 39 69 Like canoixylic acid but H is replaced w th carbon group titEnoRJ Au i Amide 39 39 i LikEfrboxvlic acid but replace OH with amine quoth39 u to j Nitriles i Carbon Nitrogen triple bonds ii p c E M 3 C 11 intermolecular orces a ion forces i Very strong electrostatic interactions ii Between and cha rged ions iii Large amount of energy needed to break iv increase melting point increase boiling point m on Van der Waals intermolecular fOrces between molecules i Dipoledipole 1 Polar molecules Orient head to tail 3 increase boiling point ii Hydrogen bonds 1 Strong interaction between hydrogen and N I39 or F iii Dispersion forces 1 Very weal Temporary induced dipoles 3 increase boiling point Solubilitys quotlike dissolves like i Polar dissolves polar nonpolar dissolves nonpolar 39ii Hydrophilicr dissolve in water iii Hydrophobic do not like vvateryr donquott dissolve 12 How reactions happen a b c d Substitution one group replaces another Addition all parts of reagent appear in product Elimination one molecule loses the atoms that become another small molecule Rearrangement molecules rearrange atoms 13 Bronsted iLova a b Acid donates protons Ht l Base accepts protons li I 14 Strong vs Weak Acids a shrine a 15 Stability a Smaller pKa more acidity Large plia weaker acidgt stronger conjugate base Smaller pKa9 stronger acid9 weaker conjugate base MEMORIZE TABLE 31 Equilibrium favors the side of the weaker acid h UFI x 7 a f Iii n r 7 3931 c g r in 1 quot 39 it w wantier Qu ll Stable anion more acidic 7 i More eiectronegative atom V JLCLF 39 139 ii Larger atom iii More resonance iv inductive electron Withdrawing v More 5 character
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