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1 EM 494 Special Topics in hemistry Illinois at hicago EM Prof. Duncan Wardrop September 17, 2012
2 ourse Website Syllabus ourse Policies ther handouts Announcements (ourse News) ourse alendar Illinois at hicago EM 494, Fall 2012 Slide 2
3 Periodicity Illinois at hicago EM 494, Fall 2012 Slide 3
4 Periodicity Illinois at hicago EM 494, Fall 2012 Slide 4
5 Lecture Summary Revision & Proof of Resonance Introduction to ydrocarbons lassification Structure & Bonding Illinois at hicago EM 494, Fall 2012 Slide 5
6 Revision of Resonance Do not confuse equilibrium with resonance: double-headed arrows represent resonance contributors; two separate arrows represent the equilibrium of distinct chemical species... Me Me Resonance (electrons move) Equilibrium (atoms move) Illinois at hicago EM 494, Fall 2012 Slide 6
7 Prioritizing Resonance ontributors (ow much Unicorn?!) Priority 1 No first-row elements (B,, N, ) can have more than eight electrons in its valence shell... N N N Equal ontributor Equal ontributor Non-Permissable ontributor (N has 10 elect.) Illinois at hicago EM 494, Fall 2012 Slide 7
8 Prioritizing Resonance ontributors Priority 2 Resonance structures in which all atoms are surrounded by an octet of electrons are almost always lower in energy than those resonance structures in which one or more atoms are electron deficient. 8 electrons 8 electrons - Bond Length 6 electrons 120 pm (=) 128 pm (calculated) 143 pm (-) More Stable Illinois at hicago EM 494, Fall 2012 Slide 8
9 Prioritizing Resonance ontributors Priority 3 Resonance structures with charge separation are typically higher in energy than those without. If charge separation exists, then electropositive atoms (, B) are better able to bear + charge... Major ontributor Unimportant ontributor Physical Evidence Small Dipole Moment 0.66 D Illinois at hicago EM 494, Fall 2012 Slide 9
10 Prioritizing Resonance ontributors Priority 4 If charge separation exists in a resonance structure, then the electronegative atoms should gain the formal negative charge and vice versa: Unimportant ontributor Major ontributor Minor (but significant) ontributor 4.02 D Illinois at hicago EM 494, Fall 2012 Slide 10
11 Self Test Question Rank the following acids in order of increasing acidity. a. b. c S d. e. + S N N + A. a, c, b, e, d B. e, c, a, b, d. c, e, a, d, b D. b, a, c, d, e E. d, b, a, c, e Illinois at hicago EM 494, Fall 2012 Slide 11
12 Self Text Question Which is the most acidic proton in the molecule below? d c e b a A. a B. b. c D. d E. e Illinois at hicago EM 494, Fall 2012 Slide 12
13 EM 494 Special Topics in hemistry Illinois at hicago lasses, Bonding & Structural Features of ydrocarbons
14 lasses of ydrocarbons ydrocarbons Aliphatic aleiphar Greek for fat sources were fats and oils only & atoms framework for funct. groups generally, non-reactive Aromatic aka: arenes many isolated from plants; impurities can be fragrant aromaticity definition: h. 12 Alkanes only single bonds nomenclature: -ane suffix Alkenes contain a double bond nomenclature: -ene suffix Alkynes contain a triple bond nomenclature: -yne suffix Illinois at hicago EM 494, Fall 2012 Slide 14
15 Examples of Aliphatic ydrocarbons butane 1-butene 1-butyne Alkanes only single bonds n 2n+2 nomenclature: -ane suffix Alkenes contain a double bond n2n (1 double bond) nomenclature: -ene suffix Illinois at hicago EM 494, Fall 2012 Alkynes contain a triple bond n2n-2 (1 triple bond) nomenclature: -yne suffix Slide 15
16 Examples of Aromatic ydrocarbons Aromatic aka: arenes many isolated from plants; impurities were fragrant aromaticity definition: h. 12 many are derivatives of benzene resonance: delocalized electrons adjacent double bonds planar (120º bond angles) polyaromatic hydrocarbons (PAs) contain two or more aromatic rings; highly carcinogenic and environmental toxin benzene benzene 3 N toluene napthalene pyridine furan Illinois at hicago EM 494, Fall 2012 Slide 16
17 Structural Features of Simple Alkanes 4 bonds to carbon, 1 bond to bond length ~ 110 pm bond length ~ 153 pm all bond angles are nearly tetrahedral Illinois at hicago EM 494, Fall 2012 Slide 17
18 Initial Valence Bond Model of arbon 1s 1s 2s carbon only has two half-filled orbitals should, then, form two bonds actually forms 4 bonds!?!? 2p 2p 2p Illinois at hicago EM 494, Fall 2012 Slide 18
19 Valence Bond Model: ybridization 2p 2p 2p mix s & p orbitals 2s Illinois at hicago EM 494, Fall 2012 sp 3 sp 3 sp 3 sp 3 hybrids: mixture of s & p; sp 3 lower in energy than p 25% s-character and 75% p-character 4 degenerate orbitals = equal in energy each half-filled, can form 4 bonds VSEPR: tetrahedral (bond angles = 109.5º) Slide 19
20 Understanding the Shape of sp 3 rbitals + constructive interference x3 destructive interference constructive interference: reinforce electron wave where sign is the same destructive interference: cancel out wave where sign is opposite higher probability of finding an electron on one side of the nucleus Illinois at hicago EM 494, Fall 2012 Slide 20
21 Sigma Bonds (σ-bond) in Methane (2sp 3 ) (1s) σ-bond 109.5º = group is pointing toward you, in front of the plane of paper = group is pointing away from you, behind the plane of paper = group is either toward or away from you, usually denotes mixtures = group lies in the plane of the drawing surface σ-bond: head-to-head overlap of orbitals; strongest bond type hybridization increases bond strength of σ-bonds since electrons are concentrated on one side of nucleus only larger lobe of sp 3 involved in bonding typically ignore (don t draw) smaller lobe Illinois at hicago EM 494, Fall 2012 Slide 21
22 The σ-bond in Ethane in-phase overlap of an sp 3 -hybridized orbital from each carbon atom overlap is along internuclear axis (σ-bond) VSEPR: tetrahedral around each carbon atom Illinois at hicago EM 494, Fall 2012 Slide 22
23 EM 494 Special Topics in hemistry Illinois at hicago Nomenclature of ydrocarbons
24 What s In a Name? IUPA: ethyl (3R,4R,5S)-5-amino-4-acetamido-3- (pentan-3-yloxy)cyclohex-1-ene-1-carboxylate Generic: oseltamivir Trade: Tamiflu 3 N IUPA: N,N-diethyltoluamide Initialism: DEET Trade: FF 3 3 IUPA: sodium dodecyl sulfate ommon: sodium lauryl sulfate Trade: SDS IUPA: Sodium (2S)-2-amino-5- hydroxy-5-oxo-pentanoate ommon: mono sodium glutamate Initialism: MSG l l l IUPA: 1,6-Dichloro-1,6- dideoxy-β-d-fructofuranosyl-4- chloro-4-deoxy-α-dgalactopyranoside ommon: sucralose Trade: Splenda Illinois at hicago EM 494, Fall 2012 Slide 24
25 IUPA: Alkanes with N Substituents IUPA: International Union of Pure and Applied hemistry common name retained Greek prefixes Illinois at hicago EM 494, Fall 2012 Slide 25
26 onstitutional (Structural) Isomers constitutional isomers: same molecular formula; different connectivity connectivity: order in which the atoms are bonded Identical Illinois at hicago EM 494, Fall 2012 Slide 26
27 ommon Names for Branched Isomers of Simple Alkanes homologous series: successive members differ by a 2 group n-butane n-pentane n-hexane iso-butane iso-pentane iso-hexane methyl: 3 methylene: 2 methine: neo-pentane neo-hexane n normal straight chain 3 iso 3 3 neo 3 3 Illinois at hicago EM 494, Fall 2012 Slide 27
28 ommon Names Become Too omplex: Systematic Method of Naming is Needed Illinois at hicago EM 494, Fall 2012 Slide 28
29 IUPA: Naming Alkyl Substituent Groups substituent: atom or group other than bonded to carbon alkyl group: one atom less than an alkane Steps: 1. Identify longest continuous chain of carbon atoms. 2. Locate substituents attached to the longest continuous chain of carbon atoms. 3. Name alkane substituent by replacing -ane of parent alkane with -yl 33 Ethane 3(2)53 eptane 3(2)163 ctadecane Illinois at hicago EM 494, Fall 2012 Slide 29
30 ommon & IUPA Names of 3-arbon Alkyl Groups Illinois at hicago EM 494, Fall 2012 Slide 30
31 ommon & IUPA Names of 4-arbon Alkyl Groups Illinois at hicago EM 494, Fall 2012 Slide 31
32 arbon lassification Illinois at hicago EM 494, Fall 2012 Slide 32
33 EM 494 Special Topics in hemistry Illinois at hicago Physical Properties of Alkanes
34 rude il - Source of Alkanes distillation: (physical separation) increases branching of the hydrocarbon chains; branched hydrocarbons have better burning characteristics cracking: (chemical change) converts high molecular weight hydrocarbons to more useful, lower molecular weight fragments reforming: (chemical change) increases branching of the hydrocarbon chains; branched hydrocarbons have better burning characteristics Illinois at hicago EM 494, Fall 2012 Slide 34
35 il Refining Illinois at hicago EM 494, Fall 2012 Slide 35
36 Boiling Points Increase with # of arbons boiling point increases with increasing number of carbon atoms branched alkanes have lower boiling points than unbranched isomers Illinois at hicago EM 494, Fall 2012 Slide 36
37 X X Intermolecular Attractive Forces van der Waals forces (VWF): intermolecular attraction between neutral species 1. dipole-dipole (including hydrogen bonding) 2. dipole/induced-dipole 3. induced-dipole/induced-dipole (London dispersion) alkanes are non-polar; dipole-dipole & dipole/ induced-dipole forces absent only forces of attraction between non-polar compounds are induced-dipole/induced-dipole Illinois at hicago EM 494, Fall 2012 Slide 37
38 Induced-Dipole/Induced-Dipole (London Dispersion Forces) initial picture: centers of positive and negative charge in each individual molecule are identical green = electric field of surrounding two covalently bonded nuclei a.k.a. cumulative electron cloud Illinois at hicago EM 494, Fall 2012 Slide 38
39 Induced-Dipole/Induced-Dipole (London Dispersion Forces) induced dipole in left molecule: movement of electrons creates instantaneous dipole in left molecule constant motion of electrons in orbitals blue/red: separation of positive and negative areas of charge within the electric field of molecule caused by asymmetric distribution of electrons Illinois at hicago EM 494, Fall 2012 Slide 39
40 Induced-Dipole/Induced-Dipole (London Dispersion Forces) left dipole induces right dipole: electron cloud in right molecule spontaneously adjusts to complement left attractive force electric attraction between two molecules both electric fields fluctuate, but always in the direction that produces weak attraction more atoms = more electrons = more induced dipoles = more attractive forces = higher boiling points Illinois at hicago EM 494, Fall 2012 Slide 40
41 Induced-Dipole/Induced-Dipole (London Dispersion Forces) more atoms = more electrons = more induced dipoles = more attractive forces = higher boiling point Illinois at hicago EM 494, Fall 2012 Slide 41
42 London VWFs in Branched Alkanes Liquid at RT Gas at RT unbranched highly branched Increasing Surface Area Increasing London Dispersion Forces Illinois at hicago EM 494, Fall 2012 Slide 42
43 ontribution of London Forces to Intermolecular Interaction Energy Molecule Pair % of the Total Interaction Energy N3-N3 57 l-l 86 Br-Br 96 I-I 99 Ne-Ne Illinois at hicago EM 494, Fall 2012 Slide 43
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