Organic Chemistry Test 1 Study Guide
Organic Chemistry Test 1 Study Guide CHEM 333 001
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CHEM 321 001
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This 7 page Study Guide was uploaded by Hayley on Tuesday September 15, 2015. The Study Guide belongs to CHEM 333 001 at University of South Carolina taught by John Lavigne in Summer 2015. Since its upload, it has received 73 views. For similar materials see Organic Chemistry I in Chemistry at University of South Carolina.
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Date Created: 09/15/15
mganic Chemistry Test 1 Study Outline Exam topics to focus list given in class Orbitals A0 HO BO MO Bonding structure bond angles IHD formal charge etc Functional Groups AcidBase Ideas Arrow pushing Intermolecular Interaction Orbitals Orbitals A0 HO BO MO HOmixed orbitals with 1 atom MOmixed orbitals with all atoms over entire molecule BOuse hybrid orbitals to study bonds Basics of Orbitals most information from 2nd language book Bond forms when an e39 of one atom overlaps with the e39 of another atom Thus 2 electrons are shared between both atoms aka the bond Orbitals are the region of space where electrons are located Focus on s and p orbitals o Atoms in second row of periodic table C N O and F have one S orbital and three P orbitals in the valence shell How do figure out the orbitals and hybridization 0 Add the number of bonded atoms to the number of lone pairs 0 This gives you hybridized orbitals Sum of orbitals amp Leftover Bonded lone hybridization pairs 4 4 sp3 3 3 sp2 1p orbital 2 2 sp 2p orbital o A carbon with 4 single bonds is sp3 hybridized o A carbon with a double bond is sp2 hybridized o A carbon with a triple bon is sp hybridized Geometry paired with Hybridization States 0 Valance Shell Electron Pair Repulsion Theory VSEPR sp3 Tetrahedral sp2 Trigonal planar sp linear o All e39 in outermost shell want to get far away from each other 0 Graph below shows simple hybridization and their geometry Lone pairs can changes things 0 The eome of the molecule is affected tetrahedral Tri onal 39dal bent Tri onal lanar bent linear Notice when there are no lone pairs the geometry matches the table above Bond Angles o sp3 1095 o spz 120 0 sp 180 Need to know 0 o are sigma bonds that represent single bonds 0 lo and 1T are sigma and pi bonds represent double bonds 0 lo and ZTE represent a triple bond Bonding Structure Bonds 0 Ionic o Gives away e39 cation o Accepts e39 anion 39 0 Very strong bonds with a high melting point 0 Example NaCl 0 Covalent 0 Share e39 Trends Electronegativity Measure of the tendency of an atom to attract a bonding pair of e39 o Eneglt 5 polar o Eneg lt 19 amp gt5 polar covalent o Eneg gt19 ionic gt Hi o The smaller the atom the more electronegativity it has Polar Vs Nonpolar 0 Non polar 0 Same atom CC 0 Same column CSi 0 Polar 0 Same side 0 Same row but not same atom Bond line diagrams o Bends and end are carbons 0 Write out heteroatoms Index of Hydrogen Deficiency IHD o How to find out degree of saturation how many hydrogen s are missing 0 For each degree there are multiple bonds or cycle double or triple bonds 0 2n2 of hydrogen s 2 0 Example I C4H1o is fully saturated because it follows CnH2n2 I C3H6 is not fully saturated because it doesn t follow CnH2n2 when the math is done using the above formula we see that we need 2 double bonds Resonance Structure Arrow Pushing o More than one way to draw a molecule 0 Way molecules become more stable 0 More e39 in multiple bonds 1t bonds 0 Think of e39 as clouds 0 Electron density 0 Using arrows 0 Do not break a single bond 0 Do not exceed the octet from second row elements 0 Tail of arrow must come from bond or lone pair 0 Head of arrow must form a bond or lone pair 0 Have a pi bond double next to positive charge 0 Positive charge is moved over 0 There are other scenarios like this on page 38 of 2rld language book Isomers o Conformational 0 Same molecular formula but different orientation in space same connectivity o Constitutional 0 Same molecular formula but different connectivity Bonding rules 1 Only valence e39 look at periodic table 2 Connectivity neutral species H X1 bond 3 lone pair of e39 C4 bonds no lone pairs N3 bonds 1 lone pair 02 bonds 2 lone pairs Bond line diagrams IDH Resonance structures Isomers constitutional amp conformational 3 Formal Charge a of valence e39 of unshared 12 shared e39 OR of valence e39 sticks stones sticksbonds and stoneslone pairs i for example sticks would be the number of bonds to that atom and the stones would be the number of lone pairs you see around the same atom 1 lone pair 2 stones 4 Bond angles 5 Bond length 6 Bond strengths FOP 999699 Functional Groups 1 2 3 4 5 6 7 8 9 1 Di Tri Tetra enta hexa Naming o If you have a double or a triple bond the name will change 0 Example 5carbon chain is pent e with all single bonds but if there is a double bond the name will change to Pentge If there is a triple bond the name will change to pentm Functional groups 0 Carboxylic Acid 0 Suffix is oic acid 0 Formula is ORCOH o Ester o Suffix is oate 0 Formula is ORCOR o Ether 0 Formula is R OR 0 Example COC oxygen has 2 lone pairs 0 Aldehyde o Suffix is al 0 Formula is ORCH o Ketone o Suffix is one 0 Formula is ORCR 0 Alcohol 0 Suffix is 01 0 Formula is ROH o Amine remember IUST nitrogen o Suffix is amine 0 Formula is 39 RNHz 39 RzNH 39 IhN o Amide nitrogen and oxygen 0 Formula 39 ORCNH2 I ORCNHR I ORCNR Rquot o Nitrile o Formulais RCEN o Alkanes o CH and CC Bonds single bond 0 Suffix is ane o Alkene 0 Double bond 0 RHCCH2 many others 0 Suffix is ene o Alkyne 0 Triple bond O RCECH O RCECR o Suffix is yne Alcohol Alkyl halides and Amine can be Primary Secondary or tertiary pKa Values 0 Alkane 50 Alkene 4246 Alkyne 2226 Ketone 1820 Amine 3842 Alcohol 1618 Phenol 911 Ammonium 911 CH3C02H Carboxylic Acid 45 Hydronium 174 Protonated oxygen alcohol ketone aldehyde ester 2ish HCl 6 H1 9 Large pKa means it s a weak acid strong conjugate base Intermolecular Interactions Remember that like dissolves likequot Types of forces 1 Ionic a Strongest b Usually opposite sides of PT c Example NaCl 2 Hydrogen Bonding a Molecules with a covalent bond between an H atom and either F O N 3 Dipoledipole a Polar molecules 4 London dispersion forces a Everything has this b Weakest c Nonpolar hydrophobic d Involve CH interactions Acid Base Chemistry All about the stability of the charged species Arrhenius H OH39 BronstedLowry acid H donorbase H acceptor Lewis acids e39 acceptor base e39 donor All Bronsted Lowry acids are Lewis acids Yes All Lewis acids are BronstedLowry acids No Equilibrium lies toward weaker acids The larger the pKa the weaker the acid
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