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Organic Chemistry

by: Brendan Smith

Organic Chemistry CH 241

Brendan Smith
Chemeketa Community College
GPA 3.59

Janice Cammack

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Janice Cammack
Class Notes
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This 2 page Class Notes was uploaded by Brendan Smith on Monday October 5, 2015. The Class Notes belongs to CH 241 at Chemeketa Community College taught by Janice Cammack in Fall. Since its upload, it has received 34 views. For similar materials see /class/219430/ch-241-chemeketa-community-college in Chemistry at Chemeketa Community College.

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Date Created: 10/05/15
Chem 241 Review for Exam 3 Final 1208 McMuIry 7 Ed Objectives You should be able to 1 Perform objectives for Exams 1 and 2 given on previous sheets Chapter 8 Alkynes Intro to Organic Synthesis Topics Covered I Naming alkynes Enyne vicinal Electrophilic addition and elimination reactions tautomers Lindlar catalyst Acetylide anions 0 Synthesis reactions You should be able to 1 Name acyclic and cyclic alkynes and draw structures corresponding to names 2 Predict the relative stability of alkyne bonds 3 Show reactions of preparation of alkynes Dehydrohalogenation of vicinal dihalides o 2KOH ethanol or o 2NaNH2 NH3 0 Alkylation of acetylide anions o NaNH2 2 RCH2X 4 Predict the products of electrophilic or radical additions to alkenes remember regiochemistry and stereochemistry 0 Addition of hydrogen halides O l or 2 eq HX ether Markovnikov regiochemistry or O 1 0 2 eq HX H202 nonMarkovnikov 0 Addition of water and alcohols o H H2O or ROH including carbocation rearrangements Markovnikov Addition of halogens in o nonpolar solvent 1 or 2 eq X2 CH2C12 anti stereochemistry or o polar solvent 1 or 2 eq X2 H2O or 1 or 2 eq X2 R OH Warkovnikov arm Oxymercuration o ngSO4 H2304 H20 0 HydroborationOXidation o 1 BHR2 2 H202 NaOH H20 0 Reduction 0 Hydrogenation 2H2 PdC or PtC or Ni to alkane o Hydrogenation H2 Lindlar s cat to cis alkene 0 Li or Na NH3 to trans alkene Correctly show the mechanism of addition reactions to alkynes Perform tautomerization of enols and carbonyls and apply it to alkyne chemistry Predict and compare the stability of saturated and unsaturated carbocation intermediates Predict the relative acidities of hydrocarbons and the strength of their corresponding bases 9 Perform substitution reactions on alkynes using acetylide anion intermediates 10 Synthesize a target molecule from a given starting material using reactions known to you 11 Summarize the industrial uses of acetylene 9 F EJ39 Chapter 9 Stereochemistry Topics Covered Handedness chiral plane of symmetry achiral chiral center planepolarized light Optical activity devorotatory dextrorotatory speci c rotation Stereoisomers enantiomers diastereomers meso Con guration absolutie con guration racemate resolution Prochirality re face Si face prochiral center pro R proS You should be able to l 2 3 4 V39 10 ll 12 14 15 Distinguish between Constitutional isomers and Stereoisomers Recognize stereogenic centers and identify them as R or S De ne and distinguish plane of symmetry chirality polarimeter speci c rotation Compare and contrast the physical and chemical properties of enantiomers and diasteriomers Locate the symmetry plane of a meso compound Predict and draw the 39wedgeanddash structures and the Fisher projections of stereoisomers Calculate the number of possible stereoisomers from the number of stereogenic centers Distinguish between dextrorotatory and levorotatory Calculate the percent optical purity if given the enantiomeric excess Distinguish between and identify speci c erythro threo and meso isomers Develop a plan for chemically resolving a racemic mixture Distinguish between absolute and relative con guration Distinguish between enantiotopic and diastereotopic hydrogens Label as proR or proS Distinguish between a regioselective stereoselective and a stereospeci c reaction Predict the stereochemistry of reaction products using the concept of prochirality when appropriate


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