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