Chapter 7: Alkenes and Alkynes Properties and Synthesis. Elimination Reactions
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1 Chapter 7: Alkenes and Alkynes Properties and Synthesis Elimination Reactions Ch 71 74: Olefins, Acetylenes, E Z System, Relative stability of alkenes, Cycloalkenes Ch 75 76: Dehydrohalogenation (E2), Zaitsev s rule, ofmann rule Syn/Anti coplanar conformation Ch 77 78: Dehydration of alcohols (E2 / E1), Carbocation stability Molecular rearrangement (1,2 shift) Ch : Synthesis of alkynes, vic-dihalide, gem-dihalide Terminal alkynes and their use in synthesis Ch : ydrogenation, Reduction, Syn/Anti addition Dissolving metal reduction, Index of hydrogen deficiency
2 Alkene Diastereomers: Cis-Trans vs E-Z VS
3 Overall Relative Stability of Alkenes The cis isomer is less stable due to greater strain from crowding by the adjacent alkyl groups The greater the number of attached alkyl groups (ie, the more highly substituted the carbon atoms of the double bond), the greater is the alkene's stability
4 Dehydrohalogenation: Zaitsev s Rule
5 Dehydrohalogenation: Zaitsev s Rule
6 The Stereochemistry of E2 Reactions
7 Acid-Catalyzed Dehydration of Alcohols: E1 Reaction The temperature and concentration of acid required to dehydrate an alcohol depend on the structure of the alcohol substrate: Primary alcohol Secondary alcohol Tertiary alcohol General reactivity order
8 Rearrangement during Dehydration A B (80%) (20%) Path B B C 3 2 C C C C 3 C 3 B Path A The formation of the more stable alkene is the general rule (Zaitsev's rule) in the acid-catalyzed dehydration reactions of alcohols
9 ydrogenation of Alkynes to Form cis-alkenes Pd/CaCO 3 plus N Poisoned catalyst (P-2 and Lindlar s catalyst) is required to stop the hydrogenation at an alkene stage
10 Anti Addition of ydrogens to Form trans-alkenes Li Dissolving metal reduction
11 Index of ydrogen Deficiency (Degree of Unsaturatiopn) Saturated ydrocarbons Unsaturated Alkane (C n 2n+2 ) Cycloalkane (C n 2n ) Alkene (C n 2n ) Alkyne (C n 2n-2 ) Aromatic 2 2 The index of hydrogen deficiency : difference in the number of hydrogen molecules between the corresponding alkane and molecular formula of the compound under consideration ID = 1 Cyclohexane (C 6 12 ) ID = 2 ID = 2 ID = 1 Cyclohexene (C 6 10 ) ID = 3
12 Chapter 8: Alkenes and Alkynes Addition Reactions Ch 81 85: Electrophilic addition reaction, Markovnikov s rule, Regioselective reaction, hydration Ch : Oxymercuration demercuration, ydroboration Oxydation Anti-Markovnikov addition, Steric factors Ch : Anti-addition of halogens, Bromonium ion, Ionic mechanism, Stereospecific reaction, alohydrin Carbene, α-elimination Ch : Oxidation of alkenes, 1,2-Diols(glycols), syn-dihydoxylation Oxidative cleavage, Ozonolysis, Stereoselctive reaction Synthon, Synthetic equivalent
13 Addition of X to Alkenes: Markovnikov s Rule
14 Stereochemistry of the Addition of X to Alkenes
15 Alcohols from Alkenes: Oxymercuration Demercuration
16 Alcohols from Alkenes: ydroboration Oxidation Syn Addition
17 Stereospecific Reactions Reaction 1 S S + (R,R)-isomer
18 Stereospecific Reactions Reaction 2 S R = (R,S)-isomer (meso)
19 Structure and Reactions of Methylene
20 Oxidation of Alkenes: Syn-1,2-Dihydroxylation
21 Oxidative Cleavage Alkenes: Ozonolysis Zn OAc O O + O + Zn(OAc) 2
22 Synthetic Strategy for Multi-step Synthesis In planning a synthesis we often have to consider four interrelated aspects: 1 Construction of the carbon skeleton 2 Functional group interconversions 3 Control of regiochemistry 4 Control of stereochemistry Retrosynthesis Synthesis
23 Chapter 11 Alcohols and Ethers Ch : Structure and nomenclature Synthesis of alcohols and ethers Reactions of alcohols (as an acid, to alkyl halides with PBr 3 and SOCl 2, to sulfonates) Ch : Synthesis of Ethers Williamson ether synthesis Alkoxymercuration Demercuration Protection groups (tert-butyl ether, Silyl ether) Ch : Epoxides (their synthesis and reactions) Anti-1,2-dihydroxylation of alkenes via epoxides Crown ethers
24 Synthesis of Alcohols from Alkenes Acid-Catalyzed ydration of alkenes Oxymercuration-Demercuration ydroboration-oxidation
25 Alkyl alide from RO: with X, PBr 3 and SOCl 2
26 Synthesis of Ethers: The Williamson Synthesis
27 Synthesis of Ethers Alkoxymercuration-Demercuration O R O R NaB 4 O R g OAc AcOg
28 Epoxides (Oxiranes)
29 Anti 1,2-Dihydroxylation of Alkenes via Epoxides O?? O trans-1,2-cyclopentadiol (R,R and S,S)
30 Chapter 12 Alcohols from Carbonyl Compounds Ch : Structure and reactivity of carbonyl group Oxidation reduction reactions (oxidation of alcohols to carbonyl groups and their reduction to alcohols) Ch : Organometallic compounds Organolithium and Organomagnesium compounds Grignard reaction Alcohols from Grignard reagents Ch 129: Organocopper reagents Lithium dialkylcuprate
31 Alcohols by Reduction of Carbonyl Compounds Lithium Aluminum ydride (LiAl 4 ) Sodium Borohydride (NaB 4 )
32 Oxidation of Primary Alcohols to Aldehydes PCC Oxidation Jones reagent Oxidation R O 2 CrO 4 R O O
33 Organometallic Compounds: Grignard Reagent Victor Grignard Novel Prize (1912)
34 Alcohols from Carbonyls and Grignard Reagents Grignard reagents react with aldehydes to give secondary alcohols Grignard reagents react with ketones to give tertiary alcohols Esters react with two molecules of Grignard reagents to form tert-alcohols
35 Summary: Synthetic Connection between Alcohols and Carbonyls
36 Synthetic Plans Based on Grignard Reaction Retrosynthetic Analysis Synthesis
37 Chapter 13 Conjugated Unsaturated System Ch : Allylic substitution, Allyl radical, Allylic chlorination Allylic bromination, N-Bromosuccinimide MO of allyl radical and allyl cation Rules for writing resonance structures Ch : Polyunsaturated hydrocarbons, 1,3-Butadiene (electron delocalization, conformation, MO) Ch Electrophilic attack on conjugated dienes Kinetic vs thermodynamic control Diels-Alder reaction (factor favoring for D-A, Stereochemistry of D-A, MO consideration, Endo/Exo-transition state, Intramolecular D-A)
38 Introduction to Conjugated Unsaturated Systems A B A B Addition A X X + A Allylic Substitution Systems that have a p orbital on an atom adjacent to a double bond with delocalized π bonds are called conjugated unsaturated systems This general phenomenon is called conjugation + Cycloaddition (Diels-Alder)
39 Allylic Bromination with N-Bromosuccinimide
40 The Stability of Allyl Radical: MO Description energy Node + + C C C Three isolated p orbitals Antibonding MO Node + Allyl Radical Nonbonding MO + Bonding MO
41 The Stability of Allyl Radical: Resonance Structures
42 The Allyl Cation e - energy Node C C C Three isolated p orbitals Antibonding MO Node Allyl Cation Nonbonding MO Bonding MO
43 The Allyl Anion e - e - energy Node C C C Three isolated p orbitals Antibonding MO Node Allyl Anion Nonbonding MO Bonding MO
44 Molecular Orbital of 1,3-Butadiene energy Node Antibonding MO p orbital LUMO Node OMO Bonding MO
45 Kinetic vs Thermodynamic Control of a Chemical Reaction
46 The Diels Alder Reaction: 1,4-Cycloaddition of Dienes In 1928 Otto Diels and Kurt Alder developed a 1,4-cycloaddition reaction of dienes that has since come to bear their names The reaction proved to be one of such great versatility and synthetic utility that Diels and Alder were awarded the Nobel Prize in Chemistry in 1950
47 Factors Favoring the Diels Alder Reaction Diels-Alder reaction is favored by the presence of electron-withdrawing groups in the dienophile and by electron-releasing groups in the diene
48 Stereochemistry of the Diels Alder Reaction 1 The Diels-Alder reaction is highly stereospecific: The reaction is a syn addition, and the configuration of the dienophile is retained in in product
49 Stereochemistry of the Diels Alder Reaction 3 The Diels-Alder reaction occurs primarily in an endo rather than an exo fashion when the reaction is kinetically controlled
50 Stereochemistry of the Diels Alder Reaction 3 The Diels-Alder reaction occurs primarily in an endo rather than an exo fashion when the reaction is kinetically controlled LUMO LUMO OMO OMO Secondary Orbital Interaction O O Primary Orbital Interactions Diene Dienophile O
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