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FIU - CHEM 2210 - CHM 2210-Organic Chemistry 1-Week 6 Notes - Class

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FIU - CHEM 2210 - CHM 2210-Organic Chemistry 1-Week 6 Notes - Class

School: Florida International University
Department: Chemistry
Course: Organic Chemistry I
Term: Spring 2014
Tags: Organic Chemistry, Chemistry, Nucleophilic Substitutions, basicity vs. nucleophilicity, Nucleophilicity, Elimination, alkylhalides, SN1, SN2, E1, E2, Stability of carbocations, aprotic, protic, and Substitution and Elimination
Name: CHM 2210-Organic Chemistry 1-Week 6 Notes
Description: These notes talk about nucleophilic substitution and elimination reactions with alkyl halides. They describe the possible ways substitution (SN1 and SN2) and elimination (E1 and E2) can occur; this usually depends on the strength/concentration of the nucleophile used (strong or weak base), the concentration of the alkyl halide, stereochemistry, carbocation stability, whether the solvent is protic o
Uploaded: 02/21/2018
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background image Alkyl halides undergo substitution reactions with nucleophiles. a. Alkyl halides undergo elimination reactions with Bronsted-Lowry bases. b. The Polar Carbon-Halogen Bond 1. sp3 hybridized C i. Nucleophile (a nucleophile may be any molecule with an unshared electron pair) ii. A leaving group is a substituent that can leave as a relatively stable entity (leaves as an anion or neutral molecule). 1) Leaving group iii. Three components are necessary in any substitution reaction. a. Alkyl Halides and Nucleophilic Substitution  2. Negatively charged nucleophiles like HO¯ and HS¯ are used as salts with Li+, Na+, or K+ counterions to balance the charge. Since the 
identity of the counterion is usually inconsequential, it is often omitted from the chemical equation.
b. When a neutral nucleophile is used, the substitution product bears a positive charge. c. Chapter 6: Ionic Reactions Nucleophilic Substitution and 
Elimination Reactions of Alkyl Halides
Monday, February 12, 2018 4:54 PM     Organic Chemistry Page 1    
background image When a neutral nucleophile is used, the substitution product bears a positive charge. c. In a nucleophilic substitution reaction of R—X, the C—X bond is heterolytically cleaved, and the leaving group departs with the electron pair  in that bond, forming X:¯. The more stable the leaving group X:¯, the better able it is to accept an electron pair.  d. Good leaving groups are weak conjugate bases (the stronger the acid, the weaker the conjugate base). e. Poor leaving groups can be turned into good leaving groups by protonation. f.     Organic Chemistry Page 2    
background image SN2 reaction: substitution, nucleophilic, 2nd order (bimolecular) a. Kinetics of a Nucleophilic Substitution Reaction: An SN2 Reaction 3. It is an unstable entity with a very brief existence (10^-12 s) i. A transition state is the high energy state of the reaction b. Both chloromethane and hydroxide are involved in the transition state and this explains why the reaction is second order i. In the transition state of this reaction bonds are partially formed and broken c. An energy diagram of a typical SN2 reaction 4.     Organic Chemistry Page 3    
background image An energy barrier is evident because a bond is being broken in going to the transition state (which is the top of the energy  barrier)  a. The difference in energy between starting material and the transition state is the free energy of activation (DG‡) b. The difference in energy between starting molecules and products is the free energy change of the reaction,  DG° c. An energy diagram of a typical SN2 reaction 4. Backside attack of nucleophile results in an inversion of configuration a. In cyclic systems a cis compound can react and become trans product b. The bond to the nucleophile in the product is always on the opposite side relative to the bond to the leaving group in the starting 
material.
i. All SN2 reactions proceed with backside attack of the nucleophile, resulting in inversion of configuration at a stereogenic center. c. The Stereochemistry of SN2 Reactions  5. SN1 reaction: Substitution, nucleophilic, 1st order (unimolecular)  a. The rate depends only on the concentration of the alkyl halide  b. Only the alkyl halide (and not the nucleophile) is involved in the transition state of the step that controls the rate c. This is called the rate-determining step  i. In multistep reactions, the rate of the slowest step will be the rate of the entire reaction  d. Key features of the SN1 mechanism are that it has two steps and involves a carbocation intermediate. e. An SN1 Reaction 6.     Organic Chemistry Page 4    

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School: Florida International University
Department: Chemistry
Course: Organic Chemistry I
Term: Spring 2014
Tags: Organic Chemistry, Chemistry, Nucleophilic Substitutions, basicity vs. nucleophilicity, Nucleophilicity, Elimination, alkylhalides, SN1, SN2, E1, E2, Stability of carbocations, aprotic, protic, and Substitution and Elimination
Name: CHM 2210-Organic Chemistry 1-Week 6 Notes
Description: These notes talk about nucleophilic substitution and elimination reactions with alkyl halides. They describe the possible ways substitution (SN1 and SN2) and elimination (E1 and E2) can occur; this usually depends on the strength/concentration of the nucleophile used (strong or weak base), the concentration of the alkyl halide, stereochemistry, carbocation stability, whether the solvent is protic o
Uploaded: 02/21/2018
13 Pages 29 Views 23 Unlocks
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