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Organic Chemistry Reaction Mechanisms

The document outlines the fundamentals of organic chemistry reaction mechanisms, including types of reactions, kinetics, and thermodynamics. It details specific mechanisms such as SN1, SN2, E1, E2, and various addition and aromatic reactions, highlighting their characteristics, rate equations, and factors affecting them. Additionally, it covers radical and pericyclic reactions, providing practice problems and references for further study.

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29 views3 pages

Organic Chemistry Reaction Mechanisms

The document outlines the fundamentals of organic chemistry reaction mechanisms, including types of reactions, kinetics, and thermodynamics. It details specific mechanisms such as SN1, SN2, E1, E2, and various addition and aromatic reactions, highlighting their characteristics, rate equations, and factors affecting them. Additionally, it covers radical and pericyclic reactions, providing practice problems and references for further study.

Uploaded by

zeeshan shoukat
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as TXT, PDF, TXT or read online on Scribd
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# Organic Chemistry: Reaction Mechanisms

## Professor Martinez | CHEM 330 | Spring 2023

## I. Fundamentals of Reaction Mechanisms

### A. Basic Concepts


- **Definition**: Reaction mechanism - step-by-step sequence showing how reactants
transform into products
- **Curved arrows**: Represent electron movement from electron-rich to electron-
poor areas
- **Types of reactions**: Substitution, elimination, addition, rearrangement
- **Intermediates vs. transition states**:
* Intermediates: Species that exist for finite time during reaction
* Transition states: Highest energy arrangements during bond breaking/forming

### B. Kinetics and Thermodynamics


- **Rate-determining step**: Slowest step in mechanism with highest energy barrier
- **Hammond's Postulate**: Transition state resembles the species closest to it in
energy
- **Gibbs Free Energy (ΔG)**: Determines spontaneity of reaction
- **Activation Energy (Ea)**: Energy barrier that must be overcome
- **Reaction coordinate diagrams**: Visual representation of energy changes during
reaction

## II. Nucleophilic Substitution Reactions

### A. SN2 Mechanism


- **Characteristics**: Concerted process, second-order kinetics
- **Stereochemistry**: Inversion of configuration at stereocenter
- **Rate equation**: Rate = k[substrate][nucleophile]
- **Factors affecting SN2**:
* Steric hindrance (methyl > primary > secondary >> tertiary)
* Nucleophile strength
* Leaving group ability
* Solvent effects (aprotic vs. protic)

### B. SN1 Mechanism


- **Steps**:
1. Slow formation of carbocation intermediate
2. Rapid attack of nucleophile
- **Stereochemistry**: Racemization with partial inversion
- **Rate equation**: Rate = k[substrate]
- **Factors affecting SN1**:
* Carbocation stability (tertiary > secondary > primary)
* Solvent polarity (polar protic solvents facilitate)
* Leaving group ability
* Nucleophile concentration (doesn't affect rate)

## III. Elimination Reactions

### A. E2 Mechanism
- **Characteristics**: Concerted process, second-order kinetics
- **Stereochemistry**: Anti-periplanar arrangement preferred
- **Zaitsev's Rule**: Major product has more substituted double bond
- **Rate equation**: Rate = k[substrate][base]
- **Competition with SN2**: Strong, bulky bases favor E2

### B. E1 Mechanism
- **Steps**:
1. Slow formation of carbocation
2. Rapid deprotonation by base/solvent
- **Stereochemistry**: No stereospecificity
- **Rate equation**: Rate = k[substrate]
- **Competition with SN1**: Cannot be separated; product ratio depends on
nucleophile/base strength

## IV. Addition Reactions

### A. Electrophilic Addition to Alkenes


- **Mechanism**:
1. Electrophile attacks π bond forming carbocation
2. Nucleophile attacks carbocation
- **Markovnikov's Rule**: H adds to less substituted carbon
- **Examples**:
* Hydrohalogenation (HX)
* Hydration (H2O/H+)
* Halogenation (X2)
- **Anti-Markovnikov addition**: Occurs with HBr and peroxides (radical mechanism)

### B. Nucleophilic Addition to Carbonyl Compounds


- **Mechanism**:
1. Nucleophile attacks electrophilic carbonyl carbon
2. Proton transfer to form product
- **Examples**:
* Grignard reactions
* Hydride reductions (NaBH4, LiAlH4)
* Cyanohydrin formation
* Imine/enamine formation

## V. Aromatic Reactions

### A. Electrophilic Aromatic Substitution


- **General mechanism**:
1. Formation of σ-complex (arenium ion)
2. Deprotonation to restore aromaticity
- **Common reactions**:
* Nitration (HNO3/H2SO4)
* Sulfonation (SO3/H2SO4)
* Halogenation (X2/FeX3)
* Friedel-Crafts alkylation (RX/AlCl3)
* Friedel-Crafts acylation (RCOCl/AlCl3)
- **Directing effects**: Activating vs. deactivating groups, ortho/para vs. meta
directors

### B. Nucleophilic Aromatic Substitution


- **SNAr Mechanism**:
1. Addition of nucleophile (Meisenheimer complex)
2. Elimination of leaving group
- **Requirements**: Electron-withdrawing groups at ortho/para positions
- **Benzyne mechanism**: Elimination-addition for unactivated aryl halides

## VI. Radical Reactions

### A. Chain Reactions


- **Initiation**: Formation of radicals (heat, light, initiators)
- **Propagation**: Radical reactions that perpetuate chain
- **Termination**: Reactions that destroy radicals
- **Examples**:
* Halogenation of alkanes
* Anti-Markovnikov addition of HBr
* Polymerization reactions

## VII. Pericyclic Reactions

### A. Cycloadditions
- **Diels-Alder reaction**: [4+2] cycloaddition between diene and dienophile
- **Frontier molecular orbital theory**: HOMO-LUMO interactions
- **Stereochemistry**: Endo vs. exo product

### B. Electrocyclic Reactions


- **Conrotatory vs. disrotatory ring closure/opening**
- **Woodward-Hoffmann rules**: Based on orbital symmetry

## Practice Problems:
1. Predict the product and draw the mechanism for the reaction of 2-bromopropane
with sodium hydroxide.
2. Compare SN1 and SN2 mechanisms for the reaction of alkyl halides with various
nucleophiles.
3. Draw the mechanism for the acid-catalyzed dehydration of cyclohexanol.

## References:
- Clayden, J., Greeves, N., & Warren, S. (2012). Organic Chemistry (2nd ed.).
Oxford University Press.
- Smith, M. B. (2019). March's Advanced Organic Chemistry (8th ed.). Wiley.

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