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Ch. 7 Study guide

by: Lindsey Rae

Ch. 7 Study guide CHEM 3101

Lindsey Rae

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a review of Ch 7.
Organic Chemistry I
John Balyeat
Study Guide
Organic Chemistry
50 ?




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This 1 page Study Guide was uploaded by Lindsey Rae on Tuesday March 8, 2016. The Study Guide belongs to CHEM 3101 at University of Colorado Colorado Springs taught by John Balyeat in Winter 2016. Since its upload, it has received 31 views.

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Date Created: 03/08/16
Ch. 7 Concepts review 7.1  Substitution reactions exchange one functional group for another The electrophile is called the substrate and it must contain a leaving group. 7.2 Two ways to name halogenated compounds: halo alkane or alkyl halide  The alpha position is the carbon atom connected directly to the halogen The Beta position is the carbons connected to the alpha position Alkyl halides are classified as primary, secondary or tertiary according to the number of groups attached to the alpha  position 7.3 Concerted process: nucleophilic attack and loss of leaving group occur simultaneously Stepwise process: leaving group goes first, then the nucleophile attacks. 7.4 Evidence for the concerted mechanism is SN2, includes the observation of a second­order rate equation and is said to be  bimolecular Methyl halides and primary alkyl halides react most quickly while tertiary are unreactive toward SN2 When the alpha position is a chirality center the reaction proceeds with inversion of configuration. The preference for  back­side attack stems from the need for constructive overlap of orbitals. SN2 rxn’s are said to be stereospecific because  the configuration of the product is determined by the configuration of the substrate.   7.5 Evidence for stepwise= SN1, includes the observation of a first order rate equation. These reactions are unimolecular First step of SN1 process is the rate­determining step The carbocation intermediate can be attacked from either side, leading to inversion of configuration and retention of  configuration. 7.6 A proton transfer is necessary at the beginning of SN1 if the substrate is an alcohol. A carbocation rearrangement can take place if it will lead to a more stable carbocation intermediate. PT is necessary at the end of SN1 if the nucleophile is not negatively charged When a solvent functions as a nucleophile, the reaction is called a solvolysis reaction 7.7  A proton transfer is necessary at the beginning of SN2 if the leaving group is OH A PT must occur at the end of SN2 if the nucleophile is neutral 7.8  Four factors that impact the competition between the SN2 mechanism and the SN1: (1)substrate, (2) the nucleophile, (3)  the leaving group, (4) the solvent The most common leaving groups are hallides and sulfonate ions. Of the sulfonate ions, the most common is the tosylate  group Protic solvents favor SN1, while polar aprotic solvents favor SN2 7.9 Depending on the type of nucleophile used, substitution reactions can be used to produce a wide range of compounds. 


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