the chemical reactivity of organic molecules come from their functional groups
DESCRIPTION
The chemical reactivity of organic molecules come from their FUNCTIONAL GROUPS. Regardless of size!. Carbon-hydrogen backbones can stand alone…. …or they can combine with other elements like O,N,S,Cl,Br,F , etc…. … and each combination will have distinct physi -chemical properties. - PowerPoint PPT PresentationTRANSCRIPT
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The chemical reactivity of organic molecules come from their FUNCTIONAL GROUPS
Regardless of size!
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Carbon-hydrogen backbones can stand alone…
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…or they can combine with other elements like O,N,S,Cl,Br,F, etc…
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… and each combination will have distinct physi-chemical properties.
Solubility (polar? Nonpolar?) Reactivity (pi bonds? Steric
hindrance? Etc..) Stable in acids? Bases? Reactive
with…? Electronegative-electropositive
regions:
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Section 3.5-3.9: Organic Reactions
CH21 – 12.10.13 , R.D. Bolinas
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Moving onto alkenes and alkynes, and other functional groups, we now have more reactive species. Why?
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Four major types of Organic Reactions:
ADDITION REACTIONS: reactants combine without anything leaving to form a product.
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Four major types of Organic Reactions:
ELIMINATION REACTIONS: reactant usually gives off atoms/has leaving groups. The product usually becomes more unsaturated/ forms a double/triple bond.
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Four major types of Organic Reactions:
SUBSTITUTION REACTIONS: reactants exchange groups, like –H and others to give two new products
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Four major types of Organic Reactions:
REARRANGEMENT REACTIONS: one reactant reorganizes its own bonds to form an isomer.
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Exercise: IDENTIFY!
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Exercise: IDENTIFY!
catalyst
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Exercise: IDENTIFY!
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Reaction Mechanisms
Knowing the reaction type is just the beginning.
To really appreciate how we form our products and what we form, we need to study REACTION MECHANISMS
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Reaction Mechanisms
“A mechanism describes what takes place at each stage of a chemical transformation—which bonds are broken and in what order, which bonds are formed and in what order, and what the relative rates of the steps are.”
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Reaction Mechanisms
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Reaction mechanisms entail the movement of electrons
The movement of electrons can be…
Between TWO molecules that collide with each other
In pairs (polar reactions)
WITHIN ONE molecule (internal)
Unpaired/solo (RADICAL reactions)
VS.
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The two major overarching mechanisms use arrows to show this…
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Radical reactions have: initiation, propagation, then termination steps.
Initiation: Chemical bond breaking occurs. This can sometimes be done with RADIATION. The breaking bond makes free radicals.
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Radical reactions have: initiation, propagation, then termination steps.
PROPAGATION: BOTH Chemical bond breaking and forming occurs. When a single radical reacts with a normal compound, one product will still be a free radical.
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Radical reactions have: initiation, propagation, then termination steps.
TERMINATION: TWO free radicals can pair up their unpaired electrons to finally form a stable covalent bond. This ends the reactions.
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Polar processes are the more common mechanism
Recall electronegativity and polarity Recall how many functional groups
have atoms that can make them polar
Recall also how opposite charges attract
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In polar mechanisms, electrons move from Nucleophile to Electrophile.
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In polar mechanisms, electrons move from Nucleophile to Electrophile.
Nucleophiles (Nu) – “Nucleus-loving” attracted to positive charges because it is
RICH IN ELECTRONS/ negative
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In polar mechanisms, electrons move from Nucleophile to Electrophile.
Electrophiles (E) – “Electron-loving” attracted to negative charges because it is
POOR IN ELECTRONS/ positive
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In polar mechanisms, electrons move from Nucleophile to Electrophile.
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In polar mechanisms, electrons move from Nucleophile to Electrophile.
Note that neutral compounds can often react either as nucleophiles or as electrophiles, depending on the circumstances. (e.g. H2O)
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Exercises: follow the arrow!
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Exercises: follow the arrow!
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Exercises: follow the arrow!
TOO LAZY to make this white.
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Exercises: follow the arrow!
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Exercises: follow the arrow!
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Exercises: follow the arrow!
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Exercises: follow the arrow!
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Sample mechanism, and how to analyze and follow it
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The mechanism is noted as an ELECTOPHILIC ADDITION
Which is the Nucleophile? The Electrophile?
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When we plot ENERGY DIAGRAMS, we can match a mechanism with THERMODYNAMIC INFO.
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Terms to remember
Reactants = where we start.Transition states = the in-
betweens usually with bonds halfway broken and half-formed, and are almost impossible to isolate.
Intermediates = another kind of in-between but more of a quick “rest-stop” form we can sometimes isolate and identify. It has its own structure (no “half-bonds”)
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Terms to remember
Activation Energy = shown as the height of a hump RELATIVE TO WHERE THE BASE IS (either the products-level or an intermediate-level). This is the energy needed to be overcome for the reaction to move forward.
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Terms to remember
Total Energy Change = this is the change in energy level from reactants to products.
A positive one (going net up) means it is ENDOGENIC and absorbs energy, so it is not as favorable.
A negative change (going net down) means the reaction is EXOGENIC and releases energy as the reaction progresses and is more favorable.
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Catalysts
LOWER ACTIVATION ENERGY!
DIFFERENT PATHWAY/ MECHANISM
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Exercises: Draw the arrows
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Exercises: Draw the arrows
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Exercises: Draw the arrows
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Exercises: Draw the arrows
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Exercises: follow the arrow!
YOU CAN DO IT! ^____^
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Exercises: follow the arrow!
OMGWTH?!!?!
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Exercises: follow the arrow!