ORGANIC CHEMISTRY I
ORGANIC CHEMISTRY I CHEM 333
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This 4 page Class Notes was uploaded by Willow Hessel on Monday October 26, 2015. The Class Notes belongs to CHEM 333 at University of South Carolina - Columbia taught by Ta Bryson in Fall. Since its upload, it has received 53 views. For similar materials see /class/229607/chem-333-university-of-south-carolina-columbia in Chemistry and Biochemistry at University of South Carolina - Columbia.
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Date Created: 10/26/15
Outcomes The following general concepts should be mastered by the end of the semester Athreedimensional view of carbon compounds based on hybridization covalent and ionic bonding The properties and reactivity generally imparted to organic structures with speci c functional groups The nomenclature and classi cation of organic compounds based on functional groups and structure Speci cally writing accurate namesIUPAC and some common for organic structures alkanes alkenes halides alcohols alkynes ethers epoxides and some organometallic compounds and translating compound names into a precise structural drawing These concepts need to be understood for problem solving during the progression of this semester for the second semester of organic chemistry and for advanced chemistries as well as other related disciplines biochemistry biology premed pharmacy chemical engineering etc Speci c concepts Chapter 1 Some of these concepts have been covered in an introductory chemistry course 39 Be able to write Lewis structures and the octet rule know the rule and some elements which often present common exceptions to it Understand electronegativity Know the difference between polar and nonpolar covalent bonds as well as ionic bonds Be able to calculate the formal charges for speci c atoms within molecules and the formal charges on molecules overall Recognize functional groups all the ones to be discussed this semester including alcohols amines aldehydes ketones carboxylic acids amides esters ethersepoxides halides Based the periodic table write the electronic con gurations of atoms Be able to draw suitable resonance structures of speci c molecules you may be given Be able to determine whether or not a given resonance structure is important Given two or more suitable resonance structures be able to determine which one is preferred Hybridized orbitals and molecular shape know the bond angles for various hybridization states Chapter 2 39 Be able to write and interpret nomenclature of alkanes Be able to recognize isomers both constitutional and geometric cistrans or diastereomeric Be able to visualize the conformations shapes of alkanes and cycloalkanes Know how to read and write Newman structures using staggered gauche eclipsed and anti displays Be able to understand the dynamics of cyclohexane chair axial equatorial boat twistboat conformations Be able to designate the most stable chair conformation Practice drawing these conformations in standard form Know about the different kinds of molecular strain angle strain torsional strain and non bonded interaction strain to be able to identify more stable and less stable conformations cistrans isomerismactually a form of diastereoisomerism Chapter 3 39 Be able to recognize stereogenic centers within molecules and also be able to recognize chiral and achiral molecules Chapte Chapte Chapte Chapte Be able to differentiate the different types of stereoisomers diastereomers enantiomers and meso compounds from one another Be able to apply the Cahn IngoldPrelog rules to designate stereogenic centers as R or S Be familiar with the equations for speci c rotation and enantiomeric excess and how to apply them What are racemic mixtures r 4 Some of these concepts have been covered in an introductory chemistry course Know the de nitions of BronsteadLowry acids and Lewis acids Understand the terms acid base conjugate acid and conjugate base Understand the criteria that help determine acidity electronegativity hybridization resonance inductive effect and the relative sizes of the atoms Know how to use the periodic table as a guide here Know how pKa is defined in terms of an equilibrium equation Be able to predict the direction of equilibrium in an acidbase reaction of common acidsbases or given a pKa s Develop a sense of acid strength of organic compounds relative to common acids of introductory chemistry r 5 Know the molecular structure and nomenclature of alkenes based on TE and 0 bonds p and sp2 hybridized orbitals Be able to designate cistrans isomerism using the cistrans andor EZ Be familiar with polyene nomeclature and which ones are conjugated r 6 Understand potential energy progress of reaction diagrams including characteristics like starting materials activation energy transition state intermediates products How does activation energy affect reaction rates Understand electrophilic addition to alkenes by HX H20 HOX X2 H2 BH3 and oxymercuration including mechanisms with electronic arrows and the stereochemical implications Know the relative stability of carbocations 1quot 2 3quot etc Understand the basis of Markovnikov s rule Be familiar with hydroboration as an example of formation of quotantiMarkovnikov productquot Be familiar with reactions with OsO4 KMnO4 03 What is the effect of substitution and conjugation on the stability of alkenes r 7 How can alkynes be reduced to alkanes Know the ways to make either cis or trans alkenes from an alkyne Know the reagents and the mechanisms as discussed in class How are alkynes converted to carbonyls BH3 disiamylborane Hg What is an enol How does ketoenol tautomerism affect products realized from alkyne hydroboration or mercury assisted hydration Chapte Chapte Chapte Know electrophilic additions to alkynes X2 HX Hg H20 Be familiar with regiochemistry and stereochemistry of these reactions r 8 Be able to write and interpret the IUPAC nomenclature of alkyl halides Be familiar with common names Be able to predict the products of alkane halogenation Understand the free radical substitution processes chain mechanism Be able to explain the regioselectivity of radical halogenation in terms of radical stability and the Hammond postulate ie bromination is more regioselective than the chlorination or uorination What are the stereochemistry consequences of radical reactions Recognize vinylic benzylic allylic organic systems Understand why benzylic and allylic hydrogens selectively react in free radical halogenation Understand how resonance effects free radical substitution Make sure you understand the appropriate use of fishhook arrows How is NBS used and why is it useful r 9 Be able to differentiate between nucleophilic substitution SNl SN2 and Selimination ElE2 How can the starting material solvent nucleophile and leaving group affect the competition between SN and E processes Be able to predict whether a reaction will proceed by SN2 E2 or SNl El mechanism Know how to write all the mechanisms of these reactions Understand how is the SN2 E2 reaction governed by sterics and SNlEl by electronic factors Why are allylic benzylic halides particularly reactive to unimolecular solvolysis El bimolecular SN2 E2 processes Know the di erences in trends for basicity and nucleophilicity Be able to classify solvents protic aprotic polar nonpolar and their affects on SN amp E Know the stereochemical and regiochemical outcomes of SN and E reactions Understand backside attack inversion retention racemization and Zaitsev s rule Why is the quottransor antzcoplanarquot arrangement important r 10 Know the structure nomenclature and properties of alcohols Know dipoledipole interactions and hydrogen bonding How can alcohols be converted to alkyl halides Be able to write how the hydroxyl group can be converted to a leaving group acid catalyst PBr3 SOClz or sulfonate esters mesylates and tosylates How can alcohols be dehydrated to alkenes Know the reagents and the mechanisms Know the oxidizing reagents for converting a 20 alcohols to a ketones What reagents will oxidize l0 alcohols to at the aldehyde the carboxylic acid When will a glycol enable you to cleave a carboncarbon bond Reagent and stereochemistry is necessary for cleavage Chapter 11 and 15 to 152 Be able to write and interpret the name of ethers using IUPAC rules Ethers are hydrogenbond acceptors Why Know how to prepare ethers the best Williamson ether synthesis What are epoxides How are they named How can we make them now peracids and halohydrins How can epoxides be opened How can this be used in making other compounds Know the nucleophiles that open epoxides water Gilman reagents alkoxides thiols alkynes etc What is the stereochemistry Know how epoxides are reduced with lithium aluminum hydride and the products formed Know the types of organometallic compounds How can these be made What is their basicity and nucleophilicity Be familiar with the reactions of Gilman reagents with alkyl Vinyl and aryl halides Be able to apply retrosynthetic logic to deVise syntheses of organic compounds from simpler precursors as discussed in class
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