Chapter 1. Carbon Compounds & Chemical Bonds
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1 Chapter 1 Carbon Compounds & Chemical Bonds Ch13: Ch14-8: Valence, C C Bonds (single, double, triple), Isomer (constitutional), Molecular/Structural formula, Connectivity Ionic/covalent bonds, Octet rule, Ions, Electronegativity Lewis structure, Formal charges, Resonance structures, Resonance stabilization Ch19-15: Atomic/molecular orbitals Orbital hybridization (sp 3, sp 2, sp) Sigma(σ)/Pi (π)bonds (structure of ethane/ethene/ethyne) Stereoisomer Ch116: Ch117: Molecular geometry (tetrahedral, trigonal planar, linear, trigonal pyramid, bent) Representation of structural formulas (dash, condensed, bond line, three-dimensional)
2 The Structural Theory of Organic Chemistry Valence: the measure of ability that atoms in organic compounds can form fixed number of bonds Isomer: different compounds that have the same molecular formula (Constitutional Isomer)
3 Electronegativity and Ionic Bonds Octet rule: the tendency for an atom to achieve a configuration where its valence shell contains eight electrons Electronegativity: a measure of the ability of an atom to attract electrons Ionic bonds: an attractive force between oppositely charged ions
4 Covalent Bonds and Lewis Structures Covalent bond: electron sharing between atoms with same or similar electronegativity to achieve noble gas configuration
5 Covalent Bonds and Lewis Structures Lewis structure (electron dot formula): a structure of molecules or ions showing the constituent atoms and the valence electrons NO 3, 3 PO 4, C 2 N 2, O 3
6 Formal Charges Indicator of how many electrons are gained/lost by an atom
7 Formal Charges Indicator of how many electrons are gained/lost by an atom
8 Resonance Structures Resonance structures: a tool we use for understanding structure and reactivity (not structures for the actual molecule or ion)
9 SP 3 ybrid Atomic Orbital ybridization: A mathematical process combining individual wave functions The shape of an sp 3 orbital
10 The Structure of Methane σ (sigma) bond
11 SP 2 ybrid Atomic Orbitals π (pi) bond An sp 2 -hybridized carbon
12 SP ybrid Atomic Orbitals An sp-hybridized carbon
13 Bond Lengths and Angles of Ethyne, Ethene, and Ethane sp-hybridized C sp 2 -hybridized C sp 3 -hybridized C s-character 50% 333% 25% p-character 50% 666% 75% ***The higher s-character of a carbon atom, the higher its electronegativity
14 Rule of Thumb using hybridized molecular orbitals SP 3 hybridization: Any atom in a molecule that is not a part of a double or triple bond Tetrahedral C SP 2 hybridization: Any atom in a molecule that is a part of a double bond Trigonal planar N O C C N C O C B C+ SP hybridization: Any atom in a molecule that is a part of a triple bond Linear N N N C C 3
15 Rule of Thumb using hybridized molecular orbitals What is the hybridization of the indicated atom(s) in each molecule? (a) C C 3 C (b) Me C Me Me (c) + (d) O (e) O O (f) (g) (h) (i) N (j) Me Al Me Me (k) O (l) O N
16 Chapter 2: Functional Groups Ch 21 24: ydrocarbons (Alkane, Alkene, Alkyne, Saturated & unsaturated compounds, Aromatic compounds) Dipole moment, Polar & nonpolar covalent bonds Ch : Functional groups (name and structure connectivity) General formula of compounds with specific fg (Table 23) Alkane, Alkene, Alkyne, Benzene (aromatic), aloalkane Alcohol, Ether, Amine, Carbonyl compounds Aldehyde, Ketone, Carboxylic acid, Ester, Amide Nitrile Ch 214 : ydrogen bond, Polarizability
17 Functional Group Certain arrangement of atoms with covalent bonds that has a unique structure and reactivity (function) O O O O Aspirin
18 Polar Covalent Bonds The nature of chemical bond in a molecule dictates the chemical and physical properties of the molecule Cl Cl C Cl Cl
19 Functional Group
20 Functional Group
21 Chapter 3: An Introduction to Organic Reactions Acids and Bases Ch 31: Ch 32: Ch 33-4: Substitution, Addition, Elimination, Rearrangement Reaction mechanism, etrolytic/homolytic bond cleavage Brønsted-Lowry and Lewis definition of acid/base Conjugate acid/base Carbocation and carbobanion, the use of curved arrows Ch 35-11: Strength of acid/base (K a and pk a ) and its prediction Effect of hybridization on acidity, Inductive/Resonance effect Equilibrium constant (K eq ), Standard free-energy change (ΔG ) Ch : Protonation on lone pair electrons (alcohols, amines, ethers, carbonyl compounds), Mechanism for organic reactions Acid/base reaction in nonaqueous solution, leveling effect
22 Categories of Organic Reactions Substitutions: one group replaces another Additions: two molecules becomes one Eliminations: one molecule loses the elements of another Rearrangement: Reorganization of a molecule s constituent parts
23 What s common in these reactions? Covalent bond cleavage: eterolytic bond cleavage requires polarized bond eterolytic bond cleavage often requires external assistance
24 Why acid base? Acid Base Reaction Many reactions in organic chemistry are: either acid base reaction themselves or involves acid base reaction at some stage Brønsted-Lowry definition: Acid a substance that can donate (or lose) a proton Base a substance that can accept (or remove) a proton Acid base reaction of other strong acids
25 Acid Base Reaction Lewis definition: Acid an electron pair acceptor Base a an electron pair donor Other examples of Lewis acid base reaction
26 Carbocations and Carbanions Carbocation: Ionic species with positively charged carbon atom Carbanion: Ionic species with negatively charged carbon atom Carbocations are strong Lewis acids while carbanions are strong bases (both Lewis and Brønsted)
27 The Strength of Acid / Base: Ka and pka
28 Predicting the Strength of Acid / Base The stronger the acid, the weaker will be its conjugate base (The larger the pka of the conjugate acid, the stronger the base) Can we predict the relative basicity of two bases?
29 Predicting the Strength of Acid / Base The relationship between structure (size) and acidity F - Cl- O - s e s a re c In ility b ta S Br - S - I - B a Se - The extent of electron delocalization (overall size) of the corresponding conjugate bases may correlate with the acidity
30 Predicting the Strength of Acid / Base The relationship between electronegativity and acidity
31 Predicting the Strength of Acid / Base The relationship between structure / electronegativity and acidity
32 Predicting the Strength of Acid / Base The relationship between structure / hybridization and acidity *The higher the s-character, the higher is the carbon s electronegativity C C C C C C Acidity Increases C C C C C C Basicity Increases
33 The Strength of Acid / Base: Inductive Effect Inductive Effect: propagation of bond polarity through σ-bond network (decrease with the distance)
34 The Strength of Acid / Base: Resonance Effect Resonance Effect: stabilization of the system by having resonance structures (increase with the # of equivalent resonance structures) requires energy for the change endothermic
35 Mechanism for Organic Reactions Reaction Mechanism: a step by step description of the events occurring from the starting materials to the products Step 1 Step 2 Step 3
36 Chapter 4: Alkanes Conformational Analysis & an Introduction to Synthesis Ch 41 47: Branched/unbranched alkanes, Constitutional isomers, Cycloalkanes, IUPAC system Ch : Conformation (σ-bond rotation, staggered, eclipsed, gauche, anti), Conformational analysis, Newman projection Torsional strain, Steric hindrance Ring strain (torsional/angle strain), yperconjugation Ch : Conformation of cyclohexane (chair/boat, equatorial/axial) Ring flip (upper/lower bond), Cis/trans isomers Ch : ydrogenation, Reduction of alkyl halide, Alkylation Alkynide anion, Nucleophile/electrophile Retrosynthetic analysis
37 Sigma (σ) Bond Rotation: Conformation Conformation: temporary molecular shapes resulting from σ-bond rotation Staggered Conformation Eclipsed Conformation
38 Conformational Analysis of Butane Torsional barrier = Steric hindrance + Orbital interactions
39 Chair vs Boat Conformation of Cyclohexane C 3 C 3 gauche conformation of butane Chair conformation Boat conformation eclipsed conformation of butane C 3
40 Substituted Cyclohexane: Axial vs Equatorial C 3 2 C C 3 gauche conformation of butane 38 kj/mol C 3 C 3 C 2 anti conformation of butane
41 Disubstituted Cyclohexanes: Cis Trans Isomers lower bond
42 Chemistry of Alkanes Alkanes: inert to many chemical reagent (originally called paraffins little affinity) Synthesis of alkanes and cycloalkanes Natural source: petroleum (as a mixture) Chemical synthesis: particular alkane (in pure form) ydrogenation: addition of hydrogen(s) to π-bond(s)
43 Alkylation of Terminal Alkynes
44 Planning an Organic Synthesis: Retrosynthetic Analysis
45 Chapter 5: Stereochemistry Chiral Molecules Ch 51 56: Ch 57 59: Stereochemistry, Chirality, Stereoisomers, Enantiomers Diastereomers, Mirror image, Chiral/Achiral molecules Stereogenic carbon (center), Plane of symmetry Configuration, R/S-system, Group priority, Optical activity Dextrorotatory/Levorotatory, Specific rotation Racemic forms (Racemate), Enantiomeric excess Ch : Stereoselective synthesis (dia-/enatiostereoselective) Kinetic resolution, Chiral drug, Meso compound Fisher projection formula Ch : Stereoisomerism of cyclic molecules, Retention/Inversion Relative/Absolute configurations, Resolution
46 Isomerism: Constitutional and Stereoisomers C 4 10 O O O
47 Test of Chirality: Plane of Symmetry A molecule will be judged to be chiral (or achiral) by; **the presence (or absence) of a single tetrahedral stereogenic carbon **the absence (or presence) of certain symmetry elements a plane of symmetry (also called a mirror plane is defined as an imaginary plane that bisects a molecule
48 Naming Enantiomers: The R,S -System 1 Assign a priority (or preference): based on atomic number (the higher atomic number, the higher priority) 3 C 3 1 Br 4 2 Cl 2 Assign a priority at the first point of difference (following 1) 3 C 2 1 O 4 2 2C C 3
49 Naming Enantiomers: The R,S -System 3 Look through the bond between stereogenic atom and the lowest priority group 3 C 2 1 O 4 3 C C O 2 2C C 3 C 2 C 3 4 Trace a path in sequence of the priority from 1 to 3 3 C O C C 2 C 3
50 Naming Enantiomers: The R,S -System 6 Groups containing double or triple bonds are assigned priorities as if both atoms were duplicated or triplicated, that is; O enantiomers O (S)- (+)-Carvone (Caraway seed oil) (R)-(-)-Carvone (Spearmint oil)
51 Racemic Forms (Racemate) Racemate O C 2 C 3 C 3 3 C 2 C 3 C O
52 Naming Molecules with Multi-Stereogenic Centers S R enantiomers R S diastereomers diastereomers diastereomers R R enantiomers S S (2R,3R)-2,3-dibromobutane Diastereomers have different physical properties: different mp and bp, different solubilities, and so forth Total number of stereoisomers will not exceed 2 n, where n is equal to the number of tetrahedral stereogenic centers
53 Molecules with Multi-Stereogenic Centers Meso Compounds S R Meso Compound diastereomers R R enantiomers S S Total number of stereoisomers will not exceed 2 n, where n is equal to the number of tetrahedral stereogenic centers
54 Molecules with Multi-Stereogenic Centers Fisher Projection Formula C 3 S R Br Br C 3 Br C 3 Br R R S S Br C 3 Br C 3 C 3 Vertical lines represent bonds that project behind the plane of the paper (or that lie in it) orizontal lines represent bonds that project out of the plane of the paper
55 1,2-Dimethylcyclohexane trans-1,2-dimethylcyclohexane Me Me Me Me Enantiomers Me Me Me Me diastereomers cis-1,2-dimethylcyclohexane Me Enantiomers Me 1,2-dimethylcyclohexane Me Me Identical Me Me Me Me Me Me Enantiomers Me Me
56 Chapter 6: Ionic Reactions Nucleophilic Substitution and Elimination Reactions Ch 61 68: Ch : Alkyl halide (polar bond, bond strength), Nucleophile Nucleophilic substitution, Leaving group, SN2 reaction Bimolecular, Transition state, Free energy of activation Retention and inversion of configuration, Concerted reaction SN1 reaction, Unimolecular, Multistep reaction Rate-limiting step, Intermediates, Carbocation stability yperconjugation, Racemization, Solvolysis Ch : Factors affecting rates of SN1 and SN2 reactions Steric effect, ammond Leffler postulate Nucleophilicity vs basicity, Protic/aprotic solvent Polar/nonpolar solvent, Polarizability, Nature of leaving group Ch : Elimination reactions, Dehydrohalogenation β-elimination, E1 and E2 reactions Competing reactions (SN2 vs E2, SN1 vs E1)
57 Mechanism for the SN2 Reaction OMO LUMO
58 The Stereochemistry of SN2 Reactions SN2 reactions always occur with inversion of configuration
59 The Reaction of t-bucl with O - : SN1 Reaction In the transition state that controls the rate of the reaction, hydroxide ions do not participate but only t-butyl chloride This reaction is said to be unimolecular (first order) in the rate-determining step an SN1 reaction (substitution, nucleophilic, unimolecular) Step 1
60 The Reaction of t-bucl with O - : SN1 Reaction Step 1 Step 2 Step 3
61 The Stereochemistry of SN1 Reactions
62 The most important factors that affect the relative rates of SN1 and SN2 reactions are: 1 the structure of the substrate 2 the concentration and reactivity of the nucleophile (for SN2 only) 3 the effect of the solvent 4 the nature of the leaving group General order of SN2 reaction: Rates of SN1 and SN2 Reactions
63 Rates of SN1 and SN2 Reactions The most important factors that affect the relative rates of SN1 and SN2 reactions are: 1 the structure of the substrate 2 the concentration and reactivity of the nucleophile (for SN2 only) 3 the effect of the solvent 4 the nature of the leaving group SN1 Reactions: The primary factor is the relative stability of the carbocation that is formed The rate of SN1 reaction correlates with that of carbocation stability
64 The E2 Reaction (Dehydrohalogenation)
65 The E1 Reaction Step 1 Step 2
66 Substitution (SN2, SN1) vs Elimination (E2, E1) Nu Nu Substitution Nu B Elimination B R R + R R δ R X R δ R R δ X R X δ R S N 2 S N 1 R R R R δ E2 R R X δ R R E1 X R R
methyl RX example primary RX example secondary RX example secondary RX example tertiary RX example
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