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CHE: Organic Chemistry - Study Guide

by: Andrew Ghobrial

CHE: Organic Chemistry - Study Guide CHE

Marketplace > Stony Brook University > Chemistry > CHE > CHE Organic Chemistry Study Guide
Andrew Ghobrial

Organic Chemistry

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Organic Chemistry
Study Guide
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This 5 page Study Guide was uploaded by Andrew Ghobrial on Wednesday October 15, 2014. The Study Guide belongs to CHE at Stony Brook University taught by Fowler in Fall. Since its upload, it has received 203 views. For similar materials see Organic Chemistry in Chemistry at Stony Brook University.


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Date Created: 10/15/14
CHE 326 Studv Guide Cope and Claisen Rearrangements The Cope and Claisen rearrangements are pericyclic reactions Pericyclic reactions are reactions that have a cyclic transition state The reactions proceed in a concerted method and one can have multiple bond making andor breaking components all in one step The first pericyclic reaction we studied was the Diels Alder reaction between a diene and an alkene acting as a dienophile It involved a 6 electron cyclic rearrangement of electrons See the Diels Alder study guide for more information and a molecular orbital analysis 41 Diels Alder lt3 Pericyclic Reac on Cope Rearrangement The Cope reaction also involves a cyclic rearrangement of electrons but there is no ring Cope 7 Pericyclic Reac on Scheme 1 What is going on here Imagine a fictitious reaction with two allyl radicals coming together in space The HOMO of an allyl radical on one has the same symmetry as the HOMO of the other The two unpaired electrons can interact These radicals could approach each other and form a new bond But the new bond could form at either end of the pair of radicals Scheme 2 Molecules A and B are the same molecule so in this simplest case it would not matter which way you went but if the molecules were not symmetric then one side could be favored So does this reaction occur Well actually no not as described The reaction of two radicals coming together in space is not a well known process However molecules like A certainly exist and if you heat them up their bonds can rearrange to give structure B This is known as the Cope rearrangement A real example is shown in Scheme 1 In the real transition state the geometry must look like the intermediate drawn in Scheme 2 but there is no evidence that the electrons ever become unpaired The Cope Rearrangement is an equilibrium process The direction of the equilibrium will depend upon the relative stability of the two compounds In the case shown above the equilibrium lies to the right because one double bond has more substituents These reactions are not low energy reactions You have to heat them up to make them go It is not always easy to recognize a potential Cope Rearrangement The key thing is that the reactant has to be a 15 diene like the molecule shown below 12345 Once you recognize the molecule as a 15diene you should redraw in to bring the ends together then do the bond rearrangement 5 gt 2 3 4g K redraw Cope heat In this case the driving force behind the reaction is the formation of forming a higher substituted double bond and conjugation between the double bond and the phenyl ring Sometimes the Cope gives rather unexpected products Here is a synthesis of a nine membered ring redraw S Cope redraw OxyCope Rearrangement If hydroxyl is involved there can be an extra driving force to the Cope reaction The following reaction is an example of an oxyCope reaction A hydroxyl group at the 3 or 4 position of the 15diene means that the product of the oxyCope will be a ketone H0 H0 0 Cope 6 The formation of the carbonyl group gives the reaction an added driving force Here is another example OH O O Cope The cyclic ketone has an E double bond something a bit unusual for a small ring III Problem 1 Predict the products of the following Cope reactions a Cope Wj b Cope Cope d Here is a good thinking question Hard The following 15diene is an achiral meso molecule Redraw Redraw 0 99 Y heat 3R4S34 dimethyhexa15diene It can undergo a Cope rearrangement to give a more stable diene The picture on the right shows it in the pseudo chair form that will lead to the reaction Rearrange the bonds and draw the final product Are the double bonds E or Z Problem 2 Predict the product of the following oxy Cope reactions OH HO b 31 OH T HO C Problem 3 Here is a reaction scheme that uses the oxyCope reaction another 0 0 Ho isomer TBDMSCI o 0 Et3N TBDMS TBDMS A B 0 H0 H0 Cope Ia 0 E D a What reagents would you use to convert B to C What would be the most likely other product b How do you deprotect C to make D c How do you convert D to E d What is the final product of the Cope rearrangement of E Four choices are shown below Caution this problem may make your head hurt CC3 C3vigtcigt i Claisen Rearrangement The Claisen rearrangement is closely related reaction that involves a vinyl allyl ether vinyl 1 05 Claisen S j 4pentenal T quot7 Pericyclic Reaction The reaction was originally discovered by heating up a sample of an allyl phenyl ether The product has the allyl group shifted to the ortho position of the phenol The intermediate is thought to be the keto form of the substituted phenol This tautomerizes to phenol to restore the aromaticity of the ring ox or o H T allyl keto intermediate quotnot stablequot The Claisen rearrangement is actually used more often than the Cope The two examples below show the syntheses of a ketone and an aldehyde that are an important intermediates in the fragrance industry cH O OK 3 H 7 J Claisen L Redraw JWK OH 0 Heat 0 OH 0 H O a Geraniol can be converted to a compound with the scent of coriander i The first step is the formation of a vinyl ether of gerniol Write a mechanism Hint think aldol ii Draw the structure of the Claisen product Problem 4 OH O I H geraniol b Sometimes the vinyl group is a trapped enolate J 1 LDA 0 0 K 2 Me3SiCl 1 heat H20 39 HOW How could you use this procedure to make the compound shown below 0 HO c Predict the product of this reaction 1 LDA 2 Me3SiCl heat H20 0 d The following reaction is called the Caroll rearrangement Write a mechanism O O UOEt o o Carrol W xx JV OH H O rearrangement Heat


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