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Section and Mechanism to know for chem 109b final

Section and Mechanism to know for chem 109b final - Too...

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Unformatted text preview: Too Many Reactions! Which ones do I need to know”??? Chapter 6: Aikynes 1. Addition of hydrogen halides (H81: or HCl) and Addition of halogens (BIZ and C12) 6.6 2. Addition ofwatcx to an alkyne (internal and terminal (Hg2+)) 6.7 3. Hydroboration-oxidation of Alkyne 6.8 4. Addition of hydrogen 6.9 a. Lindlar catalyst to get cis b. NafNH3 (liq) to get trans 5. Formation of Acetylidc Ion and reaction using acetylfide ion 6.11 6. Tautomerization of enol-éketo or aldehyde chapter 18 and my notes (ask me if confused) Chapter 7 : Dione Reactions 1. Isolated and conjugated reaction of a diene with HBI or HCl 7.10 2. Isolated and conjugated reaction of a diene with C12 or BIZ 7.10 3. Dials-Alder reaction 7.12. Chapter 10: Alcohols. Ethers, Epoxides, Thiols, Organometallics 1. Convarting an alcohol to an alky halide (HIBr, HI, HCI, PBr3, PCB, SOCIZ) 10.1 and 10.2 2. Converting an alcohol to a sulfonate ester 10.3 - 3. Converting an “activated alcohol” (has a good LG from above) into a compound with a new group bonded 10.3 4. Dehydration/Elimination (112804 only) 10.4 5. Nucleophilic substitution of others 10.7 6. Nucleophilic substitution of epoxides 10.8 7. Reactions of thiols with an alkyl halide 10.11 8. Founatioa of organolithium and organomagnesim (gtignard reagents) and reaction with electrophilie'or epoxide 10.12 ' 9. Formation of a Gilman Reagent and its reaction with an allcyl halide 10.13 Chapter 14: Reactions of Benzene 1. Halogenation of benzene 14.11 2. Nitration of benzene 14.12 3. Sulfonation of benzene 14.13 4. Friedel-Crafts Acylation 14.14 Chapter 16 & 17 Sections to Study for Midterm 2 a When working through the chapters, don’t get overwhelmed by the amount of sections listed—you all know most of this, it is just useful to go through the information with the book so that it can act as a study guide with explanations already set up for you. 0 Also! Remember that most of these sections are only a couple pages long and sometimes shorter! 2) Chapter 16: * know all of the carbonyl structures" 161 Study Nomenclature (to the best of your ability) 16.2 Structure of carboxylic acids and carboxylic acid derivatives 16.5 How Class 1 Carbonyl Compounds React 16.6 Relative Reactivities of Carboxylic Acids and CA Derivatives 16.7 General Mechanism for Nucleophiiic Acyl Substitution Reactions 16.8 Reactions of Acyl Halides 16.9 Reactions of Acid Anhydrides 16.10 Reactions of Esters 16.11 Aciducatalyzed ester hydrolysis and transesterification 16.12 Hydroxide—ion promoted ester hydrolysis 16.14 Soaps ' 16.15 Reactions of Carboxylic Acids 16.16 Reactions of Amides 16.17 The hydrolysis of amides is cataiyzed by acids 16.19 The hydrolysis of nitriles 16.21 How chemists activate CA 16.22 How cells activate CA 16.23 Dicarboxyiic Acids and their derivatives 0 Make sure to look at the structures of phosgene, dimethyl carbonate, and urea (he wrote them on the board) \\\\’\\\\\"\’\\\‘\’\’\\\ Chapter 17: 17.1 Nomenciature 17.2 Relative Reactivities of Carbonyl Compounds 17.3 How Aldehydes and Ketones React 17.4 Reaction of Carbonyl Compounds with Grignard Reagents 17.5 Reactions of Carbonyl Compounds with acetylide ions 17.6 Reactions of Carbonyl Compounds with Hydride Ion 17.7 Reactions of aldehydes and ketones with hydrogen cyanide 17.8 Reactions of aldehydes and ketones with amines and derivatives of amines 0 You do NOT need to know reductive amination BUT you DO need to know the wolff-kishner reduction 17.9 Reaction of aldehydes and ketones with water 17.10 Reactions of aldehydes and ketones with alcohols \’\\\\\\\ xx xxx 17.11 Protecting groups 0 Just worry about the diol protecting groups for aldehydes and ketones 17.12 Addition of sulfur nucleophiles 17.13 The wittig reaction forms an alkene 17.16 Nucleophilio Addition to alpha,beta—unsaturated aldehyde and ketones Mechanisms to Know and Love! =P From Chapter 16 (LOOK! Only SIX different mechanisms): V” Nucleophilic Acyl Substitution Reactions 0 with charged and neutral nucleophile (16.7) 0 Reactions with acyl chlorides (16.8) 0 Reactions with acid anydrides (16.9) V Acid—catalyzed ester hydrolysis and transesterification 0 Reaction of ester with water or alcohol (16.1 I) o REVERSE REACTION: Acid catalyzed reaction with carboxyiic acids and alcohol (SAME mechanism as ester. above but with carboxylic acid) (16.15) 0 Acid catalyzed substitution of amides with alcohol and water (same mechanism as above two but with amide and acid) (16.17) V’ Hydrolysis of esters with tertiary alkyi groups-Sn1 mechanism (16.11) V Hydroxidewion promoted ester hydrolysis (16.12) 0 Reaction with ester and hydroxide (you are what you are in! !) 9product is a carboxylate ion and alcohol (irreversible) ‘6 Activation of carboxylic acids with SOClZ in heat (DIFFERENT IN BOOK—in review midterm!) (16.21) \/ Look over ATP mechanism (16.22) From Chapter 17: V Addition reactions to ketones, aldehydes and group i with Strong Bases (irreversible) o Grignard Reagents (17.4) o Acetylide Ions (recall how to make an acetylide ion with NaNHZ/NH3) (17.5) o Hydride Ion from NaBH4, LiAlH4 (17.6) I Know predict products with (DIBALH) ithAlI-I, not mechanism ' Skip the carboxyiic acid mechanism but know the N—substituted amide one V Reactions with Hydrogen cyanide (Weak base—reversible) (17.7) / Imine formation mechanisms (17.8) J Enamine formation mechanism (17.8) i/ Wolfmeishner Reduction (17.8) v/ Reactions of aldehydes and ketones with watermhydrate formation (17.9) V” Reactions of aldehydes and ketones with aicohol—acetaI/ketal formation (17.10) 0 Protecting groups—just the mechanism with diois and thiols (same as acetal/ketai formation) V’ Wittig Reaction (17.13) 0 Formation of phosphonium yiide 0 Formation of Wittig product / Nucieophilic Addition of alph—beta unsaturated aldehydes and ketones (17.16) 0 1,2 (direct) addition and 1,4 (Conjugate) addition 0 Addition of NaBH4, CeC13 mechanism (NOT IN BOOK—win review midterm) o Remind yourseif what you use to form grignard reagents and giiman reagents Chapter 18 and 19: Sections and Mechanisms to Know - Chapter 18: - 0 The acidity of an alpha-hydrogen (18.1) Keto~Enol "Pantomers (18.2) Enolization (18.3) How Enols and Enolate Ions React (18.4) Haiogenation of the alphancarbon of aldehydes and ketons (18.5) Haiogenation of the alpha—carbon of carboxylic acids: HVZ (18.6) Using LDA to form an enolate ion (18.8) Alkylation of the alpha carbon of carbonyl compounds (18.9) Alkyiation and acylation of the alpha—carbon using an enamine intermediate (18.10) Alkyiation of the betaucarbon: the Michaei reaction (18.1 1) An aidol addition forms beta—hydroxyaidehydes or beta~hydroxyketones (18.12) Dehydration of aldol addition (Aidol condensation—«18.13) The mixed aldol addition (18.14) A ciaisen condensation forms a beta—keto ester (18.15) The mixed claisen condensation (18.16) Intramolecular condensation and addition (18.17) 3—oxocarboxylic acids can be decarboxylated (18.18) Malonic ester synthesis (18.19) Acetoacetic ester synthesis (18.20) COCOCOCGOG Mechansims: o Keto-enoi tautomerization (18.3) o Halogenation (18.5) I Acid and base catalyzed ' haioform Halogenation of carboxylic acids (HV Z) (18.6) A1ky1ation of alpha carbons (18.9) I Using LDA, etc. Using enamine intermediate for alkylation and acylation (18.10 and 18.11) Michael reaction (18.1 1) Aldoi addition (18.12) Aldoi condensation (18.13) Ciaisen condensation (18.15, 18.16) Condensation of ketone and ester (18.16) lntramolecuiar (18.17) Robinson Annulation (1 8.17) Decarboxylation (1 8.18) Malonic ester and acetoacetic ester synthesis (18.19 and 18.20) 00 0000000000 Chapter 19: 0 Reduction reactions (19.1) Oxidation of alcohols (19.2) Oxidation of aldehydes and ketones (19.3) Hydroxylation of alkenes (19.5) Oxidative cleavage of 1,2 diols (19.6) Oxidative Cleave of aikenes (19.7) Oxidation of alcohols (10.5) .9000. Mechanisms: o Oxidation of alcohols by chromic acid (shown in packet sent home)—-10.5 0 Review previousiy learned mechanisms if covered 0 See extreme packet emailed home for mechanism (NOT MAN Y AT ALL!)— know how to predict these products of oxidation and reductions ...
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