Chem 120 Reactions of Hydrocarbons

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Presentation Transcript

Slide 1: 

HABIT IS DIFFICULT TO CHANGE Take away the H, you have ABIT, Take away the A, you still have BIT of it, and even after taking the B, you will still have IT. So, make sure we pick up GOOD NURSING HABITS

Slide 2: 

Reaction of Alkanes

Slide 3: 

CnH2n+2 + O2 → CO2 + H2O Reaction of Alkenes Combustion

Slide 4: 

Example of Combustion

Slide 5: 

Reaction of Alkanes Combustion Cracking Types of Cracking Catalytic Cracking Zeolites Thermal Cracking 450°C to 750°C 70 atm

Slide 6: 

Features of the Reaction Alkane Reactivity Order: tertiary > secondary > primary > methyl Halogen reactivity: F2 > Cl2 > Br2 > I2 Bromination is selective for the R-H that gives the most stable radical. Chlorination is less selective Reaction of Alkanes Combustion Cracking Addition of Halogens (Halogenation)

Slide 7: 

Free Radical Reaction Mechanism of Halogenation (1) Initiation Step Reaction of Alkanes Combustion Cracking Addition of Halogens (Halogenation) Free Radical Mechanism

Slide 8: 

Free Radical Reaction Mechanism of Halogenation Initiation Step Propagation Step

Slide 9: 

Free Radical Reaction Mechanism of Halogenation Initiation Step Propagation Step Termination Step

Slide 10: 

Reaction of Alkenes

Slide 18: 

Reaction of Alkenes Addition of Hydrogen (Catalytic Hydrogenation)

Slide 19: 

Reaction of Alkenes Addition of Hydrogen (Catalytic Hydrogenation) Mechanism

Slide 20: 

Catalysts are substances that changes the rate (velocity) of a chemical reaction without being consumed or appearing as part of the product.

Slide 21: 

Reaction of Alkenes Addition of Hydrogen (Catalytic Hydrogenation) Mechanism Addition of Hydrogen Halides (Hydrohalogenation)

Slide 22: 

Reaction of Alkenes Addition of Hydrogen (Catalytic Hydrogenation) Mechanism Addition of Hydrogen Halides (Hydrohalogenation) Mechanism

Slide 23: 

Markovnikov’s Rule “when an unsymmetrically substituted alkene reacts with a hydrogen halide, the hydrogen adds to the carbon that has the greater number of hydrogen substituents, and the halogen adds to the carbon having fewer hydrogen substituents” Reaction of Alkenes Addition of Hydrogen (Catalytic Hydrogenation) Mechanism Addition of Hydrogen Halides (Hydrohalogenation) Mechanism Markovnikov's Rule

Slide 24: 

Example of Hydrohalogenation

Slide 25: 

Example of Hydrohalogenation

Slide 26: 

Example of Hydrohalogenation

Slide 27: 

The Peroxide Effect Reverses the effect of Markovnikov’s Rule (Anti-Markovnikov) Reaction of Alkenes Addition of Hydrogen (Catalytic Hydrogenation) Mechanism Addition of Hydrogen Halides (Hydrohalogenation) Mechanism Markovnikov's Rule The Peroxide Effect

Slide 28: 

Example of the Peroxide Effect on Hydrohalogenation

Slide 29: 

Reaction of Alkenes Addition of Hydrogen (Catalytic Hydrogenation) Mechanism Addition of Hydrogen Halides (Hydrohalogenation) Mechanism Markovnikov's Rule The Peroxide Effect Carbocation Rearrangements

Slide 30: 

Example of the Carbocation Rearrangement on Alkene Addition Reactions

Slide 31: 

Also follows Markovinikov’s Rule Reaction of Alkenes Addition of Hydrogen (Catalytic Hydrogenation) Mechanism Addition of Hydrogen Halides (Hydrohalogenation) Mechanism Markovnikov's Rule The Peroxide Effect Carbocation Rearrangements Addition of Sulfuric Acid

Slide 33: 

Also follows Markovinikov’s Rule Reaction of Alkenes Addition of Hydrogen (Catalytic Hydrogenation) Mechanism Addition of Hydrogen Halides (Hydrohalogenation) Mechanism Markovnikov's Rule The Peroxide Effect Carbocation Rearrangements Addition of Sulfuric Acid Addition of Water (Hydration)

Slide 34: 

Example of Alkene Hydration

Slide 35: 

Example of Alkene Hydration

Slide 36: 

Practice on Alkene Addition Reactions

Slide 37: 

Practice on Alkene Addition Reactions

Slide 38: 

Practice on Alkene Addition Reactions

Slide 39: 

Reaction of Alkenes Addition of Hydrogen (Catalytic Hydrogenation) Mechanism Addition of Hydrogen Halides (Hydrohalogenation) Mechanism Markovnikov's Rule The Peroxide Effect Carbocation Rearrangements Addition of Sulfuric Acid Addition of Water (Hydration) Addition of Halogens (Halogenation)

Slide 40: 

No carbocation intermediate like in hydrohalogenation No Carbocation Rearrangements occur

Slide 41: 

Reaction of Alkenes Addition of Hydrogen (Catalytic Hydrogenation) Mechanism Addition of Hydrogen Halides (Hydrohalogenation) Mechanism Markovnikov's Rule The Peroxide Effect Carbocation Rearrangements Addition of Sulfuric Acid Addition of Water (Hydration) Addition of Halogens (Halogenation) Mechanism

Slide 42: 

Reaction of Alkenes Addition of Hydrogen (Catalytic Hydrogenation) Mechanism Addition of Hydrogen Halides (Hydrohalogenation) Mechanism Markovnikov's Rule The Peroxide Effect Carbocation Rearrangements Addition of Sulfuric Acid Addition of Water (Hydration) Addition of Halogens (Halogenation) Mechanism Addition of Halogen and Water (Halohydrin Formation)

Slide 43: 

Example of Alkene Halohydrin Formation

Slide 44: 

Water will attach to the more substituted carbon Halogen will attach to the less substituted carbon Example of Alkene Halohydrin Formation

Slide 45: 

Reaction of Alkenes Addition of Hydrogen (Catalytic Hydrogenation) Mechanism Addition of Hydrogen Halides (Hydrohalogenation) Mechanism Markovnikov's Rule The Peroxide Effect Carbocation Rearrangements Addition of Sulfuric Acid Addition of Water (Hydration) Addition of Halogens (Halogenation) Mechanism Addition of Halogen and Water (Halohydrin Formation) Mechanism

Slide 46: 

Reagents KMnO4 (cold, dilute, alkaline potassium permanganate) OsO4 (osmium tetroxide) in pyridine Reaction of Alkenes Addition of Hydrogen (Catalytic Hydrogenation) Mechanism Addition of Hydrogen Halides (Hydrohalogenation) Mechanism Markovnikov's Rule The Peroxide Effect Carbocation Rearrangements Addition of Sulfuric Acid Addition of Water (Hydration) Addition of Halogens (Halogenation) Mechanism Addition of Halogen and Water (Halohydrin Formation) Mechanism Hydroxylation

Slide 47: 

Example of Alkene Addition Reactions

Slide 48: 

Reagents 1. O3 (ozone); 2. H2O, Zn 1. O3 ,CH3OH (methanol); 2. (CH3)2S (dimethyl sulfide, DMS) Reaction of Alkenes Addition of Hydrogen (Catalytic Hydrogenation) Mechanism Addition of Hydrogen Halides (Hydrohalogenation) Mechanism Markovnikov's Rule The Peroxide Effect Carbocation Rearrangements Addition of Sulfuric Acid Addition of Water (Hydration) Addition of Halogens (Halogenation) Mechanism Addition of Halogen and Water (Halohydrin Formation) Mechanism Hydroxylation Ozonolysis

Slide 49: 

Ozonolysis Mechanism Oxygen gas is exposed to high voltage to form ozone (03) Ozone reacts with the alkene to form a molozonide intermediate. The molozonide intermediate then breaks down into two fragments. These two fragments then rearrange to form an ozonide intermediate. Reduction of the ozonide with a reducing agent (e.g., zinc metal in acetic acid or dimethyl sulfide) then results in cleavage of the ozonide into two carbonyl compounds. Reaction of Alkenes Addition of Hydrogen (Catalytic Hydrogenation) Mechanism Addition of Hydrogen Halides (Hydrohalogenation) Mechanism Markovnikov's Rule The Peroxide Effect Carbocation Rearrangements Addition of Sulfuric Acid Addition of Water (Hydration) Addition of Halogens (Halogenation) Mechanism Addition of Halogen and Water (Halohydrin Formation) Mechanism Hydroxylation Ozonolysis Mechanism

Slide 50: 

Practice on Alkene Ozonolysis Propose a starting product for the following ozonolysis reactions

Slide 51: 

Practice on Alkene Ozonolysis

Slide 52: 

Practice on Alkene Ozonolysis

Slide 53: 

Reagents Hot alkaline potassium permanganate followed by acidification Reaction of Alkenes Addition of Hydrogen (Catalytic Hydrogenation) Mechanism Addition of Hydrogen Halides (Hydrohalogenation) Mechanism Markovnikov's Rule The Peroxide Effect Carbocation Rearrangements Addition of Sulfuric Acid Addition of Water (Hydration) Addition of Halogens (Halogenation) Mechanism Addition of Halogen and Water (Halohydrin Formation) Mechanism Hydroxylation Ozonolysis Mechanism Oxidation with hot alkaline KMnO4 followed by acidification.

Slide 54: 

Reaction of Alkynes

Slide 55: 

Features Produces a Geminal Dihalide Reaction proceeds through a carbocation intermediate Reaction of Alkynes Addition of HCl and HBr

Slide 56: 

Practice on Alkyne Hydrohalogenation Predict the products of these reactions

Slide 57: 

Practice on Alkyne Hydrohalogenation Predict the products of these reactions

Slide 58: 

Features Produces a trans-dihaloalkane Then, a tetrahaloalkane Reaction of Alkynes Addition of HCl and HBr Addition of Halogen

Slide 59: 

Practice on Alkyne Halogenation Predict the products of these reactions

Slide 60: 

Keto-Enol Tautomerism Enol (ene+ol) rearranges immediately to a ketone Tautomers are constitutional isomers that interconvert rapidly Water will attack the more substituted carbon (Markovnikov) Reaction of Alkynes Addition of HCl and HBr Addition of Halogen Hydration Acid-catalyzed Hydration

Slide 61: 

Practice on Alkyne Acid Catalyzed Hydration Predict the products of these reactions

Slide 62: 

Internal Alkynes produces ketones Terminal Alkynes produces a methyl ketone

Slide 63: 

Reaction of Alkynes Addition of HCl and HBr Addition of Halogen Hydration Acid-catalyzed Hydration Oxymercuration-Demercuration Markovnikov Reagents Mercuric acetate (Hg(Oac)2) Sodium borohydride (NaBH4)

Slide 64: 

Anti-Markovnikov Reaction of Alkynes Addition of HCl and HBr Addition of Halogen Hydration Acid-catalyzed Hydration Oxymercuration-Demercuration Hydroboration-Oxidation

Slide 65: 

Example on Internal Alkyne Hydroboration-Oxidation Hydroborane would attack the less substituted carbon,

Slide 66: 

Example on Terminal Alkyne Hydroboration-Oxidation Hydroborane would attack the less substituted carbon thus producing an aldehyde rather than a ketone

Slide 67: 

Let’s compare Acid Catalyzed Hydration and Hydroboration-Oxidation

Slide 68: 

Catalytic Hydrogenation with Palladium in Carbon will produce an alkane Reaction of Alkynes Addition of HCl and HBr Addition of Halogen Hydration Acid-catalyzed Hydration Oxymercuration-Demercuration Hydroboration-Oxidation Reduction Catalytic Hydrogenation Alkane Product Pd/C

Slide 69: 

Catalytic Hydrogenation with Lindlar Catalyst will produce a cis-Alkene Reaction of Alkynes Addition of HCl and HBr Addition of Halogen Hydration Acid-catalyzed Hydration Oxymercuration-Demercuration Hydroboration-Oxidation Reduction Catalytic Hydrogenation Alkane Product Pd/C Cis alkene product Lindlar’s Catalyst

Slide 70: 

Practice on Alkyne Catalytic Hydrogenation Predict the products of these reactions

Slide 71: 

Hydroboration-dehydration will produce an alkene Reaction of Alkynes Addition of HCl and HBr Addition of Halogen Hydration Acid-catalyzed Hydration Oxymercuration-Demercuration Hydroboration-Oxidation Reduction Catalytic Hydrogenation Alkane Product Pd/C Cis alkene product Lindlar’s Catalyst Hydroboration-Dehydration

Slide 72: 

Catalytic Hydrogenation with Lithium in Ammonia will produce a trans-Alkene Reaction of Alkynes Addition of HCl and HBr Addition of Halogen Hydration Acid-catalyzed Hydration Oxymercuration-Demercuration Hydroboration-Oxidation Reduction Catalytic Hydrogenation Alkane Product Pd/C Cis alkene product Lindlar’s Catalyst Hydroboration-Dehydration Trans alkene product Li in NH3

Slide 73: 

Practice on Alkyne Catalytic Hydrogenation Predict the product of this reaction

Slide 74: 

Reaction of Alkynes Addition of HCl and HBr Addition of Halogen Hydration Acid-catalyzed Hydration Oxymercuration-Demercuration Hydroboration-Oxidation Reduction Catalytic Hydrogenation Alkane Product Pd/C Cis alkene product Lindlar’s Catalyst Hydroboration-Dehydration Trans alkene product Li in NH3 Oxidative Cleavage Acidic KMnO4 or Ozonolysis

Slide 75: 

Due to the acidity of a terminal alkyne, sodium amide in ammonia will produce an acetylide anion Reaction of Alkynes Addition of HCl and HBr Addition of Halogen Hydration Acid-catalyzed Hydration Oxymercuration-Demercuration Hydroboration-Oxidation Reduction Catalytic Hydrogenation Alkane Product Pd/C Cis alkene product Lindlar’s Catalyst Hydroboration-Dehydration Trans alkene product Li in NH3 Oxidative Cleavage Acidic KMnO4 or Ozonolysis Conversion to Acetylide Anions

Slide 76: 

The alkyl group of the alkyl halide will be added to the end of the acetylide anion thus making a bigger alkyne chain. Reaction of Alkynes Addition of HCl and HBr Addition of Halogen Hydration Acid-catalyzed Hydration Oxymercuration-Demercuration Hydroboration-Oxidation Reduction Catalytic Hydrogenation Alkane Product Pd/C Cis alkene product Lindlar’s Catalyst Hydroboration-Dehydration Trans alkene product Li in NH3 Oxidative Cleavage Acidic KMnO4 or Ozonolysis Conversion to Acetylide Anions Alkylation of Acetylide Anions

Slide 77: 

Practice on Alkyne Alkylation Predict the product of this reaction

Slide 78: 

Practice on Alkyne Alkylation Predict the product of this reaction