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Organic Chemistry 2 Exam 1 Study Guide

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by: Hayley Lecker

Organic Chemistry 2 Exam 1 Study Guide CHEM 2325 - 001

Marketplace > University of Texas at El Paso > CHEM 2325 - 001 > Organic Chemistry 2 Exam 1 Study Guide
Hayley Lecker
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About this Document

This is a study guide for exam 1 covering the main topics that will be on the exam.
Organic Chemistry - 12551
James Salvador
Study Guide
Organic Chemistry, UTEP, University of Texas at El Paso, Organic Chemistry 2, Ochem
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This 8 page Study Guide was uploaded by Hayley Lecker on Saturday February 6, 2016. The Study Guide belongs to CHEM 2325 - 001 at University of Texas at El Paso taught by James Salvador in Fall 2015. Since its upload, it has received 203 views.


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Date Created: 02/06/16
OrganicChemistry 2 Exam1Study Guide Alkyl Halides with Bases NaOH will produce a Sayefft elimination. Meaning the MOST substituted is the best choose. Example: Cl with NaOH the double bond would be between carbon 2, where the Cl is and carbon 3 where the methyl is. This would give KO will produce to the Hoffman product, this means the less substituted choose the product in this case. Example: Cl KO with If this was Sayefft elimination the double bond would go to either the left or right side of the pentane, but since it is not the double bond will be formed at the methyl. That would be . Rate of Reaction SN1 VS. SN2 SN1 reacts the fastest with tertiary, then secondary and finally primary. However, primary will likely go through SN2 instead. Example: < Primary will usually go SN2 SN2 is the opposite where primary reacts the fastest, then secondary, then tertiary is the slowest. If you see there methyls react even faster than primary. Stereochemistry of SN1 VS. SN2 SN1 will result in a mixture of isomers. SN2 will led to the inversion of the chiral center, HOWEVER if the new substitution has higher prority the chirality could stay the same! Mechanism SN1 VS. SN2 Rate of Reaction E1 VS E2 E1’s rate of reaction is determined by the carbocation that can be formed. Tertiary is the fastest, then secondary, and finally primary. However with primary there may be a rearrangement. In E2 the carbocation does not determine the rate of reaction. Unlike E1, E2 requires a strong base. Stereochemistry of E1 VS E2 Both reactions follow Sayzefft’s rule (if possible) meaning that the most substituted is the best option. However with E2 the leaving group MUST be anti the hydrogen that is being removed. So the first choice for Sayzefft may not be the correct one. Mechanism of E1 VS E2 Water with Alkyl Halides This type of reaction is nucleophilic substitution, and the alkyl halide is converted to an alcohol. The water is the nucleophile. This type of reaction isn’t common since alkyl halides are usually prepared from alcohols. Water falls under the SN1 mechanism. Triphenylphosphine with Alkyl Halides Triphenylphosphine will react with primary or secondary alkyl halides ONLY! This is because the reaction is a Wittig reaction that proceeds like an SN2. Primary reacts faster than secondary. Alkene Reactions Below are Alkene addition reaction with orientation and stereochemistry. Markovnikov's rule (Markovnikov addition): In an addition reaction of a protic acid HX (hydrogen chloride, hydrogen bromide, or hydrogen iodide) to an alkene or alkyne, the hydrogen atom of HX becomes bonded to the carbon atom that had the greatest number of hydrogen atoms in the starting alkene or alkyne. Anti-Markovnikov addition: In an addition reaction of a generic electrophile HX to an alkene or alkyne, the hydrogen atom of HX becomes bonded to the carbon atom that had the least number of hydrogen atoms in the starting alkene or alkyne. Notes for 13: If it is Ozone (O3 AND ZN) two ketones/aldehydes will be formed instead of example above. Alkyne Reactions Hydroboration Hydrogenation NOTE THIS IS SYN (CIS) Hydrogenation- Lindlar Catalyst Notes: IT DOES THE SAME AS JUST H2! Sodium Reduction This is an anti or trans addition! Oxymercuration Hydrohalogenation Example: With Excess Bromine Radical Addition Notes: When treated with 1 equivalent of HBr in the presence of oxygen or peroxides (even UV LIGHT!) an alkyne forms a vinyl bromide, this promotes radical addition and instead of Markovnikov this is anti markovnikov. Halogenation This is a trans addition, if in excess it will go from X-C(DOUBLE BOND)C-X to X2-C-CX2.


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