Organic reactions
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Organic Reactions. Kinds of Reactions Mechanisms (polar, non-polar) Bond Dissociation Energy Reaction Profiles. Types of Reactions. Addition Reactions Elimination Reactions. Types of Reactions. Substitution: Polar Non-polar. Rearrangement. Definitions.

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Organic reactions

Organic Reactions

Kinds of Reactions

Mechanisms (polar, non-polar)

Bond Dissociation Energy

Reaction Profiles


Types of reactions
Types of Reactions

  • Addition Reactions

  • Elimination Reactions


Types of reactions1
Types of Reactions

  • Substitution:

    • Polar

    • Non-polar



Definitions
Definitions

  • Mechanism: Complete step-by-step of exactly which bonds break and which bonds form and in what order.

  • Thermodynamics: The study of the energy changes that occur in chemical transformations. This allows for comparison of stability of reactants and products.

  • Kinetics: The study of reaction rates, determining which products are formed most rapidly. One can predict how the rate will change with changing conditions.



2 nd order reaction
2nd Order Reaction


1 st order reaction
1st Order Reaction


Bond breaking non polar and polar
Bond Breaking:Non-polar and Polar


Bond forming non polar and polar
Bond Forming:Non-polar and Polar





Experimental evidence helps to determine mechanism
Experimental Evidence Helps to Determine Mechanism

  • Chlorination does not occur at room temperature in the dark.

  • The most effective wavelength of light is blue that is strongly absorbed by Cl2 gas.

  • The light-initiated reaction has a high quantum yield (many molecules of product are formed from each photon of light).




Organic reactions
Enthalpy of Reaction ( ReactionDHo) Measures Difference in Strength of Bonds Broken and Bonds FormedBond Dissociation Energy


Organic reactions

D ReactionHo = Sbonds broken-Sbonds formed


D h rxn 105 kj mol
D ReactionHrxn = -105 kJ/mol





Chlorination of methylpropane
Chlorination Reactionof Methylpropane



3 o radicals are easiest to form
3 H’s in chlorination reactionso Radicals are Easiest to Form


Stability of free radicals
Stability of Free Radicals H’s in chlorination reactions


Bromination is very selective
Bromination is Very Selective H’s in chlorination reactions


Rds in bromination is highly endothermic
RDS in H’s in chlorination reactionsBromination is highly endothermic


Organic reactions

Consider the free radical H’s in chlorination reactionsmonochlorination of 2,2,5-trimethylhexane. Draw all of the unique products (ignore stereoisomers; use zig-zag structures please) and predict the ratio or percent composition of the products.The relative reactivity of H abstraction in a chlorination reaction: 1o: 2o: 3o = 1: 4.5: 5.5


Chlorofluorocarbons and the depletion of ozone
Chlorofluorocarbons and the Depletion of Ozone H’s in chlorination reactions


Polar reactions nucleophiles electrophiles
Polar Reactions: H’s in chlorination reactionsNucleophiles & Electrophiles


Nucleophiles are bases electrophiles are acids
Nucleophiles are Bases H’s in chlorination reactionsElectrophiles are Acids


Addition of hbr to ethylene
Addition of H’s in chlorination reactionsHBr to Ethylene


Reactions often go through intermediates
Reactions Often Go Through H’s in chlorination reactionsIntermediates


Transition state
Transition State H’s in chlorination reactions


Addition reaction is a two step mechanism
Addition Reaction is a Two-Step Mechanism H’s in chlorination reactions


Organic reactions
How Many Mechanistic Steps? H’s in chlorination reactionsHow Many Intermediates?How Many Transition States?Which Step is Rate-Determining?