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Organic Chemistry 1 Lecture 3 CHEM 232 University of Illinois Organic Chemistry I at Chicago UIC Organic Chemistry 1 Lecture 3 Instructor: Prof. Duncan Wardrop Time/Day: T & R, 12:30-1:45 p.m. January 19, 2010 1 Lecture Summary Revision & Proof of Resonance Introduction to Hydrocarbons Classi!cation Structure & Bonding Nomenclature University of Slide 2 CHEM 232, Spring 2010 Illinois at Chicago UIC Lecture 3: January 19 2 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.... O O Resonance (electrons move) MeO MeO H O O H H H Equilibrium (atoms move) University of Slide 3 CHEM 232, Spring 2010 Illinois at Chicago UIC Lecture 3: January 19 3 The first pair of structures are descriptions of the same molecule - the overall description is based on a weighted combination of the two extremes. The second pair of structures are distinct molecules: one is a ketone and the other an enol. For more details about this chemical transformation, see Chapter 18. Prioritizing Resonance Contributors (How much Unicorn?!) Priority 1 No !rst-row elements (B, C, N, O) can have more than eight electrons in its valence shell..... O O O N N N O O O Equal Equal Non-Permissable Contributor Contributor Contributor (N has 10 elect.) University of Slide 4 CHEM 232, Spring 2010 Illinois at Chicago UIC Lecture 3: January 19 4 Prioritizing Resonance Contributors 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 de!cient. 8 electrons 8 electrons H H H O O O C-O Bond Length 120 pm (C=O) 6 electrons 128 pm (calculated) 143 pm (C-O) More Stable University of Slide 5 CHEM 232, Spring 2010 Illinois at Chicago UIC Lecture 3: January 19 5 Prioritizing Resonance Contributors Priority 3 Resonance structures with charge separation are typically higher in energy than those without. If charge separation exists, then electropositive atoms (C, B) are better able to bear +ve charge... Small Dipole Moment Major Unimportant Physical Contributor Contributor Evidence H H H H H H 0.66 D University of Slide 6 CHEM 232, Spring 2010 Illinois at Chicago UIC Lecture 3: January 19 6 Prioritizing Resonance Contributors Priority 4 If charge separation exists in a resonance structure, then the electronegative atoms should gain the formal negative charge and vice versa: O O O Unimportant Major Minor Contributor Contributor (but significant) 4.02 D Contributor University of Slide 7 CHEM 232, Spring 2010 Illinois at Chicago UIC Lecture 3: January 19 7 Self Test Question Rank the following acids in order of increasing acidity. a. O + H OH O d. O + H O b. O SH S + H OH O A. a, c, b, e, d H N e. N + H B. e, c, a, b, d c. C. c, e, a, d, b OH O + H D. b, a, c, d, e E. d, b, a, c, e University of Slide 8 CHEM 232, Spring 2010 Illinois at Chicago UIC Lecture 3: January 19 8 There are a number of structural features which effect the pKa of an acid: a) Electronegativity; b) The strength of the bond to the acidic hydrogen atom; c) Inductive effects; d) Resonance delocalization in conjugate base. Self Text Question Which is the most acidic proton in the molecule below? e A. a H H O O a B. b H H O d C. c H H H O H b D. d H c E. e University of Slide 9 CHEM 232, Spring 2010 Illinois at Chicago UIC Lecture 3: January 19 9 Free Organic Chemistry Tutoring in the SLC Where: Science & Learning Center (201 SES) Who: Dr. Bob Widing When: Tuesday & Thursday, 1-5 p.m. Monday & Wednesday afternoons Look for a molecular model set and you’ll know you’ve found the right person. If he’s in the SLC, Dr. Widing is willing to help. University of Slide 10 CHEM 232, Spring 2010 Illinois at Chicago UIC Lecture 3: January 19 10 Quiz This Week This will be the last notice about quizzes. You should expect a quiz in your discussion section every week. • Quiz this week during your discussion section • Topic = Chapter 1 • Only top ten quiz scores (25 points each) count • No makeup quizzes; minimum 12 quizzes University of Slide 11 CHEM 232, Spring 2010 Illinois at Chicago UIC Lecture 3: January 19 11 Molecular Model Set • A molecular model set is highly recommended • Essential for Chapters 3 & 7 • Any set is !ne; your preference; available in bookstore • Bring your set to class and discussion section University of Slide 12 CHEM 232, Spring 2010 Illinois at Chicago UIC Lecture 3: January 19 12 CHEM 232 University of Illinois Organic Chemistry I at Chicago UIC Classes, Bonding & Structural Features of Hydrocarbons Sections 2.1, 2.5-2.10 13 Classes of Hydrocarbons Hydrocarbons • only C & H atoms • framework for funct. groups Aliphatic • generally, non-reactive Aromatic • aka: arenes • many isolated from plants; • aleiphar Greek for “fat” impurities can be fragrant • sources were fats and oils • aromaticity de!niton: Ch. 12 Alkanes Alkenes Alkynes • only single bonds • contain a double bond • contain a triple bond • nomenclature: -ane suffix • nomenclature: -ene suffix • nomenclature: -yne suffix University of Slide 14 CHEM 232, Spring 2010 Illinois at Chicago UIC Lecture 3: January 19 14 Examples of Aliphatic Hydrocarbons butane 1-butene 1-butyne H H H H H H H H H H C C C C H H C C C C H C C C C H H H H H H H H H H H CH CH CCH CH3CH2CH2CH3 CH3CH2CHCH2 3 2 Alkanes Alkenes Alkynes • only single bonds • contain a double bond • contain a triple bond • CnH2n+2 • CnH2n (1 double bond) • CnH2n-2 (1 triple bond) • nomenclature: -ane • nomenclature: -ene • nomenclature: -yne suffix suffix suffix University of Slide 15 CHEM 232, Spring 2010 Illinois at Chicago UIC Lecture 3: January 19 15 Examples of Aromatic Hydrocarbons Aromatic • aka: arenes H • many isolated from plants; H C H C C impurities were fragrant C C • aromaticity de!niton: Ch. 12 H C H H • many are derivatives of benzene benzene benzene • resonance: delocalized electrons CH3 N • adjacent double bonds O • planar (120º bond angles) • polyaromatic hydrocarbons toluene napthalene pyridine furan (PAHs) contain two or more aromatic rings; highly carcinogenic and environmental toxin University of Slide 16 CHEM 232, Spring 2010 Illinois at Chicago UIC Lecture 3: January 19 16 Structural Features of Simple Alkanes • 4 bonds to carbon, 1 bond to H • C–H bond length ~ 110 pm • C–C bond length ~ 153 pm • all bond angles are nearly tetrahedral University of Slide 17 CHEM 232, Spring 2010 Illinois at Chicago UIC Lecture 3: January 19 17 Initial Valence Bond Model of Carbon H H 1s 1s H H C C 2p 2p 2p 2s • carbon only has two half-!lled orbitals • should, then, form two bonds • actually forms 4 bonds!?!? University of Slide 18 CHEM 232, Spring 2010 Illinois at Chicago UIC Lecture 3: January 19 18 Valence Bond Model: Hybridization 2p 2p 2p mix s & p orbitals 2s sp3 sp3 sp3 sp3 • hybrids: mixture of s & p; sp3 lower in energy than p • 25% s-character and 75% p-character • 4 degenerate orbitals = equal in energy • each half-!lled, can form 4 bonds • VSEPR: tetrahedral (bond angles = 109.5º) University of Slide 19 CHEM 232, Spring 2010 Illinois at Chicago UIC Lecture 3: January 19 19 Understanding the Shape of sp3 Orbitals constructive + interference + + – + – destructive + – interference x3 • constructive interference: reinforce electron wave where sign is the same • destructive interference: cancel out wave where sign is opposite • higher probability of !nding an electron on one side of the nucleus University of Slide 20 CHEM 232, Spring 2010 Illinois at Chicago UIC Lecture 3: January 19 20 Sigma Bonds (σ-bond) in Methane = group is pointing toward you, in front of the plane of paper H C(2sp3)––H(1s) = group is pointing away σ-bond from you, behind the plane H of paper C H = group is either toward or away from you, usually denotes mixtures 109.5º H = 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 sp3 involved in bonding • typically ignore (don’t draw) smaller lobe University of Slide 21 CHEM 232, Spring 2010 Illinois at Chicago UIC Lecture 3: January 19 21 The C–C σ-bond in Ethane • in-phase overlap of an sp3-hybridized orbital from each carbon atom • overlap is along internuclear axis (σ-bond) • VSEPR: tetrahedral around each carbon atom University of Slide 22 CHEM 232, Spring 2010 Illinois at Chicago UIC Lecture 3: January 19 22 CHEM 232 University of Illinois Organic Chemistry I at Chicago UIC Nomenclature of Hydrocarbons Sections: 2.11-2.15 23 What’s In a Name? IUPAC: sodium dodecyl sulfate Common: sodium lauryl sulfate Trade: SDS IUPAC: ethyl (3R,4R,5S)-5-amino-4-acetamido-3- Cl (pentan-3-yloxy)cyclohex-1-ene-1-carboxylate Generic: oseltamivir HO Trade: Tamiflu O HO Cl O O OH O N CH3 IUPAC: Sodium (2S)-2-amino-5- HO hydroxy-5-oxo-pentanoate OH Common: mono sodium glutamate Cl H C CH : 1,6-Dichloro-1,6- 3 3 Initialism: MSG IUPAC dideoxy-β-D-fructofuranosyl-4- chloro-4-deoxy-α-D- IUPAC: N,N-diethyltoluamide galactopyranoside Initialism: DEET Common: sucralose Trade: OFF Trade: Splenda University of Slide 24 CHEM 232, Spring 2010 Illinois at Chicago UIC Lecture 3: January 19 24 IUPAC: Alkanes with NO Substituents IUPAC: International Union of Pure and Applied Chemistry common name retained Greek prefixes University of Slide 25 CHEM 232, Spring 2010 Illinois at Chicago UIC Lecture 3: January 19 25 Constitutional (Structural) Isomers constitutional isomers:
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