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Here is your exclusive access to 100+ tutoring videos. Your content includes: VSEPR, nomenclature, acids and bases, stereoisomers, SN2/ SN1/ E2/ E1, alcohols, IR and NMR spectroscopy, alkenes, ozonolysis, markovnikov vs antimarkovnikov, allylics, diels alder, alkynes, benzenes, aromaticity, aldehydes, ketones, carbonyls, and alpha carbon chemistry, carboxylic acids, carboxylic acid derivatives, esters, acyl chlorides, amides, anhydrides, nitriles, amines, nitrous amines, Hoffman elimination, diazomethane, phenol reactions, benzylic carbon, ester carbonyl, Claisen condensation, enolate reactions, Michael addition, Robinson annulation, beta dicarbonyl compounds, carbohydrates, D vs L sugars, anomers, glycosides, monosaccharides, disaccharides, heterocycles, pyridines, amino acids, peptides, proteins, and everything in between.
Quarter 1 Video Hub
Bonding— Learning goals: Predict and explain patterns in shape, structure, and bonding. Recognize when covalent versus ionic bonds exist. Apply formal charge to atoms when determining the charges of molecular species. Differentiate single bonds from double bonds. Populate lone pairs given formal charges and bond connectivity. Draw and interpret Lewis, condensed, and bond-line structures involving single and double bonds.
Resonance— Learning goals: Apply resonance and conjugation. Predict and explain patterns in stability, shape, hybridization, reactivity, and product formation when resonance or conjugation applies to a reactant, intermediate or final product. Recognize structure relationships between chemical reactions and resonance structures. Differentiate minor contributors, equal contributors, and major contributors.
Resonance 2— Learning goals: Apply resonance and conjugation. Predict and explain patterns in stability, shape, hybridization, reactivity, and product formation when resonance or conjugation applies to a reactant, intermediate or final product. Recognize structure relationships between chemical reactions and resonance structures. Differentiate minor contributors, equal contributors, and major contributors.
Resonance 3— Learning goals: Apply resonance and conjugation. Predict and explain patterns in stability, shape, hybridization, reactivity, and product formation when resonance or conjugation applies to a reactant, intermediate or final product. Recognize structure relationships between chemical reactions and resonance structures. Differentiate minor contributors, equal contributors, and major contributors.
Lewis Structures— Learning goals: Draw Lewis structures for given molecular compounds. Interpret Lewis structures and recognize lone pairs and formal charge. Identify single bonds from double bonds given a molecular formula.
Formal charge— Learning goals: Predict and explain patterns in shape, structure, and formal charge given a molecular formula. Differentiate anions from cations. Recognize and calculate formal charges and lone pairs given bond connectivity. Populate lone pairs given formal charges and bond connectivity.
Hybridization— Learning goals: Predict and explain patterns in shape, structure, formal charge, and hybridization given a molecular formula. Apply concepts of resonance and define its impact on hybridization. Identify the hybridization, electron geometry, and approximate bond angles relative to atoms in each molecule. Predict the geometry of a given molecular structure. Differentiate tetrahedral, trigonal planar, and linear from one another. Compare and contrast sp, sp2, and sp3 hybridization. Determine bond angle of specific atoms in a molecular compound. Compare sigma and pi bonds. Assign hybridization to atoms within organic molecules.
Hybridization 2— Learning goals: Predict and explain patterns in shape, structure, formal charge, and hybridization given a molecular formula. Apply concepts of resonance and define its impact on hybridization. Identify the hybridization, electron geometry, and approximate bond angles relative to atoms in each molecule. Predict the geometry of a given molecular structure. Differentiate tetrahedral, trigonal planar, and linear from one another. Compare and contrast sp, sp2, and sp3 hybridization. Determine bond angle of specific atoms in a molecular compound. Compare sigma and pi bonds. Assign hybridization to atoms within organic molecules.
Drawing structures— Learning goals: Draw and interpret Lewis, Kekule, condensed, bond-line structures, and dash-wedge structures. Elucidate stereochemistry when appropriate. Draw 3-dimensional representations of given molecules, using hash-wedge conventions. Draw various organic representations of molecules and atoms. Assign formal charges when necessary.
Condensed and bond line structures— Learning goals: Differentiate between condensed and bond-line structures. Draw various organic representations of molecules and atoms. Convert between condensed and bond line structures when drawing. Fill in all relevant lone pairs on the provided structures.
Newman projections and chair conformations— Learning goals: Convert between Newman and 3D molecular projections. Differentiate between staggered, gauche, and eclipsed conformations. Describe stability of straight-chain conformational isomers. Plot energy diagrams on a reaction coordinate diagram. Interconvert between cyclohexanes and chair conformations. Describe stability between chair conformation and flipped chair conformation. Determine axial and equatorial positions in cyclohexane and chair conformations
Formal charge, Lewis Structures, Naming R vs S, Radical Halogenation— Learning goals: Elucidate formal charge and lewis structures. Identify and name simple (straight chain) alkenes give formulas. Write formulas for straight chain alkanes given their names. Write the proper IUPAC naming conventions for various molecules. Distinguish sp3 stereocenters from sp2 hybridization and sp hybridization. Describe stereochemistry for various molecules. Incorporate R vs S Cahn Ingold Prelog naming conventions. Undergo radical halogenation for primary, secondary, and tertiary compounds with X2
Formal Charge, Hybridization, Lewis Structures, Naming, Radical Halogenation— Learning goals: Elucidate formal charge and Lewis structures. Identify and name simple (straight chain) alkenes give formulas. Write formulas for straight chain alkanes given their names. Write the proper IUPAC naming conventions for various molecules. Distinguish sp3 stereocenters from sp2 hybridization and sp hybridization. Describe stereochemistry for various molecules. Undergo radical halogenation for primary, secondary, and tertiary compounds with X2
Cyclohexanes, chairs, Stereoisomers, Enantiomers, Diastereomers, Meso, Fischer Projections— Learning goals: Draw accurate cyclohexane chair conformations, including cis- or trans. Illustrate and identify axial versus equatorial substituents on cyclohexane chair conformations. Predict most stable chair conformations. Incorporate R vs S Cahn Ingold Prelog naming conventions. Identify cis and trans relationship for the substituents on straight chain alkanes and cycloalkanes. Draw chair conformation of cyclohexane with unambiguous representation of axial and equatorial substituents. Complete the equilibrium of two chair conformational isomers for a substituted cyclohexane. Indicate the change for the relative positions of axial and equatorial substituents. Draw flipped chair conformations. Describe the stability between these two isomers. Differentiate enantiomers, diastereomers, identical chiral molecules, constitutional isomers, and meso compounds. Classify molecules as chiral or achiral and identify mirror planes of symmetry. Identify chiral carbons and identify them as R or S. Identify relationships between pairs of molecules as enantiomers, diastereomers, or equivalent, and identify when a solution is optically active or inactive. Discern structural isomers, enantiomers, diastereomers and meso compounds.
Chairs and Stereoisomers— Learning goals: Draw accurate cyclohexane chair conformations, including cis- or trans. Illustrate and identify axial versus equatorial substituents on cyclohexane chair conformations. Predict most stable chair conformations. Incorporate R vs S Cahn Ingold Prelog naming conventions. Identify cis and trans relationship for the substituents on straight chain alkanes and cycloalkanes. Draw chair conformation of cyclohexane with unambiguous representation of axial and equatorial substituents. Complete the equilibrium of two chair conformational isomers for a substituted cyclohexane. Indicate the change for the relative positions of axial and equatorial substituents. Draw flipped chair conformations. Describe the stability between these two isomers. Differentiate enantiomers, diastereomers, identical chiral molecules, constitutional isomers, and meso compounds. Classify molecules as chiral or achiral and identify mirror planes of symmetry. Identify chiral carbons and identify them as R or S. Identify relationships between pairs of molecules as enantiomers, diastereomers, or equivalent, and identify when a solution is optically active or inactive. Discern structural isomers, enantiomers, diastereomers and meso compounds.
MT2 Nomenclature, R vs. S, E vs Z, stereoisomers— Learning goals: Differentiate between R vs S terminology. Apply Cahn-Ingold-Prelog priority rules to molecules with up to four substituents to determine absolute configuration. Name cis, trans, E, and Z molecules using appropriate nomenclature. Name alkenes given R, S, Z, and E terminology. Distinguish enantiomers and diastereomers. Identify enantiomers, diastereomers, and meso compounds. Utilize chair conformations to distinguish enantiomers, diastereomers and meso compounds.
MT2 SN2 vs SN1 vs E2 vs E1— Learning goals: Distinguish nucleophiles and electrophiles from Lewis acids and bases. Compare nucleophilicity and relative strength between nucleophiles. Differentiate between strong nucleophile and poor nucleophile. Describe the relationship between electrophile and leaving group in a substitution reaction. Identify traits that increase electrophilicity. Recall the traits of a good leaving group. Recall the importance of resonance and its impact on a leaving group. Define localized and delocalized. Identify SN2, SN1, E2, and E1 reactions. Recall the traits that define SN2, SN1, E2, and E1 reactions. Propose mechanisms for SN2, SN1, E2, and E1 reactions. Predict the products and specify the reagents for SN2, SN1, E2, E1 reactions. Differentiate between SN2, SN1, E2, and E1 reactions. Define the term racemic. Describe the stereochemistry and regiochemistry for SN2, SN1, E2, E1 reactions. Describe the importance of solvents during SN2, SN1, E2, and E1 reactions. Distinguish polar protic solvents from polar aprotic solvents
MT2 IR Spectroscopy, SN2/SN1/E2/E1, Antiperiplanar— Learning goals: Distinguish downfield from upfield on the IR graph. Predict the IR peaks for common organic functional groups, including ketones, carboxylic acids, and alcohols. Elucidate peak shape on IR data and how it relates to functional groups. Distinguish broad from sharp peaks on IR data. Define the fingerprint region. Identify specific wavelength ranges on the X axis of an IR graph. Identify SN2, SN1, E2, and E1 reactions. Recall the traits that define SN2, SN1, E2, and E1 reactions. Propose mechanisms for SN2, SN1, E2, and E1 reactions. Predict the products and specify the reagents for SN2, SN1, E2, E1 reactions. Differentiate between SN2, SN1, E2, and E1 reactions. Define the term racemic. Describe the stereochemistry and regiochemistry for SN2, SN1, E2, E1 reactions. Describe the importance of solvents during SN2, SN1, E2, and E1 reactions. Distinguish polar protic solvents from polar aprotic solvents. Define Zaytsev. Define Hoffman. Describe how Zaytsev and Hoffman terms are applied in elimination reactions. Identify bulky reagents. Define antiperiplanar and how it relates to E2 reactions
MT2 SN2 SN1 E2 E1— Learning goals: Identify halocarbons as primary, secondary, or tertiary. Identify the role of a good leaving group. Describe the role of a protic solvent vs an aprotic solvent. Compare relative strengths of nucleophiles. Discern good leaving groups from poor leaving groups. Use arrow-pushing to display the flow of electrons in an organic chemistry reaction. Compare and contrast SN2 from SN1. Describe the relationship between atomic radii size and leaving group potential. Classify fundamental organic chemistry reactions such as SN2, SN1, E1 and E1. Categorize SN2 and SN1 reactions given a specific nucleophile. Identify the number of steps required in an SN2 vs SN1 reaction. Identify the role of a carbocation in an SN1 reaction. Critically evaluate formal charge throughout organic chemistry reactions. Assign formal charge to various atoms and chemical species during reactions. Differentiate covalent bonds from ionic bonds and the role of ionic bonds in fundamental organic chemistry reactions. Utilize trends from general chemistry such as electronegativity and atomic radii size. Determine relative acidity from basicity and the role of acids and bases in fundamental organic chemistry reactions. Determine the qualities of an E2 reaction.
MT2 SN2 and NMR Tutorial— Learning goals: Define the terms electrophile, nucleophile, leaving group, substrate, and reagent. Describe the role of partial positive and partial negative charges in fundamental organic chemistry reactions. Identify halocarbons as primary, secondary, or tertiary. Discern electrophiles from nucleophiles. Identify the role of a good leaving group. Describe the role of a protic solvent vs an aprotic solvent. Compare relative strengths of nucleophiles. Discern good leaving groups from poor leaving groups. Use arrow-pushing to display the flow of electrons in an organic chemistry reaction. Compare and contrast SN2 from SN1. Describe the relationship between atomic radii size and leaving group potential. Classify fundamental organic chemistry reactions such as SN2, SN1, E1 and E1. Categorize SN2 and SN1 reactions given a specific nucleophile. Identify the number of steps required in an SN2 vs SN1 reaction. Identify the role of a carbocation in an SN1 reaction. Critically evaluate formal charge throughout organic chemistry reactions. Assign formal charge to various atoms and chemical species during reactions. Differentiate covalent bonds from ionic bonds and the role of ionic bonds in fundamental organic chemistry reactions. Utilize trends from general chemistry such as electronegativity and atomic radii size. Determine relative acidity from basicity and the role of acids and bases in fundamental organic chemistry reactions. Define degree of unsaturation. Utilize NMR data to predict the structure of a molecule. Distinguish downfield from upfield on the NMR graph. Predict the NMR peaks for common organic functional groups, including ketones, carboxylic acids, and alcohols. Elucidate peak shape on NMR data and how it relates to functional groups. Identify specific PPM ranges on the X axis of an NMR graph. Describe what NMR spectroscopy measures and what it is generally used for. Recall the units for chemical shift on standardized NMR. Identify what deshielding is and how it impacts NMR spectra. Recognize key regions and peaks within an NMR spectrum. Match a compound to a given NMR spectrum analysis. Identify the role of “neighbors” in NMR graphs and its importance
MT3 (Final) IR vs NMR spectroscopy, alcohol reactions and mechanisms— Learning goals: Define degree of unsaturation. Differentiate between saturated and unsaturated fats. Utilize IR and NMR data to predict the structure of a molecule. Distinguish downfield from upfield on the IR graph. Predict the IR peaks for common organic functional groups, including ketones, carboxylic acids, and alcohols. Elucidate peak shape on IR data and how it relates to functional groups. Distinguish broad from sharp peaks on IR data. Define the fingerprint region. Identify specific wavelength ranges on the X axis of an IR graph. Describe what NMR spectroscopy measures and what it is generally used for. Recall the units for chemical shift on standardized NMR. Identify what deshielding is and how it impacts NMR spectra. Recognize key regions and peaks within an NMR spectra. Match a compound to a given NMR spectrum analysis. Identify alcohol reactions. Recall the traits that define alcohols reactions. Propose mechanisms for alcohol reactions. Predict the products and specify the reagents for alcohol reactions. Differentiate between PCC and Jones reagents. Predict the reaction of primary and secondary alcohols with strong oxidizing agents. Recall the reagent(s) used to oxidize primary alcohols to aldehydes. Recall the reagent(s) used to oxidize primary alcohols to carboxylic acids. Recall the reagent(s) used to oxidize secondary alcohols to ketones. Identify chromium in oxidation reactions. Identify oxidation-reduction reactions. Distinguish weak oxidizing agents from strong oxidizing agents. Utilize reducing agents during predict the product reactions. Define lithium aluminum hydride and its importance in reduction reactions. Draw the mechanism for reduction reactions of alcohols. Describe acid work up.
MT3 alcohol reactions grignard LiAlH4 and synthesis— Learning Goals: Predict the products and use varying reagents regarding alcohol synthesis, oxidation, reduction, grignard, and more.
MT3 alcohols ethers epoxides— Learning Goals: Predict the products and use varying reagents regarding alcohol synthesis, ethers, and epoxides.
MT3 PBr3 SOCl2 Epoxides ethers alcohol dehydration— Learning goals: Utilize reagents such as PBr3 in the dehydration of alcohols. Compare and contrast SOCl2 and PBr3. Prepare reactions using HS2O4 and alcohols. Differentiate H2SO4 in cold vs hot conditions (135 degrees vs 180 degrees F). Differentiate acidic vs basic conditions in epoxide reactions.
MT3 SN2 E2 SN1 Alcohols oxidation and reduction Jones— Learning goals: Differentiate SN2, E2, SN1 and E1 reactions. Identify big bulky bases. Differentiate monsubstituted from disubstituted, and so forth. Identify carbocations during SN1 reactions and describe carbocation rearrangements. Oxidize alcohols using PCC and Jones and conduct reduction reactions using LiAlH4. Describe the formation of ketones and aldehydes.
MT3 alcohols ethers epoxides synthesis final exam review— Learning Goals: Predict the reagent, predict the product, and conduct synthesis problems. Differentiate acidic vs basic conditions when conducting epoxide reactions. Utilize grignard reagents.
Q1 MT3 Final Exam Review Session 2 March 2022— Learning Goals: Comprehensive Final Exam Review.
Q1 MT3 High Yield Final Exam Review Session Synthesis Problems March 2022— Learning Goals: Comprehensive Final Exam Review Session with an emphasis on Synthesis style reaction problems.
Quarter 1 Video Archive Ends Here
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Introducing Quarter 2 Online Video Archive
MT1 Intro to Alkenes— Learning Goals: Elucidate alkenes from a molecular formula. Differentiate mono-substituted, di-substituted, trisubstituted, and tetrasubstituted. Discern stability among alkene species.
MT1 Lesson 02 Properties of Alkenes— Learning Goals: Recognize the properties of alkenes relative to alkanes. Differentiate boiling point and melting point. Rank acidity, reactivity and stability.
MT1 Nomenclature of Alkenes, EZ— Learning Goals: Name alkenes based on provided bond-line structures. Consider when to assign the configurations of any R/S chiral centers or E/Z double bonds.
MT1 Alkenes, E2, Zaytsev vs Hoffman, markovnikov vs antimarkovnikov— Learning Goals: Differentiate Zaytsev and Hoffman. Differentiate markovnikov vs antimarkovnikov. Identify big bulky bases. Predict the products using acid catalysts during alcohol dehydration reactions. Use H2O2 or HOOH or R2O2 or ROOR and hv with HBr.
MT1 Elimination Reactions— Learning Goals: Propose mechanisms for elimination reactions. Predict the products and specify the reagents for alkyne synthesis for elimination reactions. Differentiate between E2 and E1 reactions. Describe the stereochemistry the stereochemistry for E2 and E1 reactions as they relate to alkenes.
MT1 Elimination Reactions 2— Learning Goals: Propose mechanisms for elimination reactions. Predict the products and specify the reagents for alkyne synthesis for elimination reactions. Differentiate between E2 and E1 reactions. Describe the stereochemistry the stereochemistry for E2 and E1 reactions as they relate to alkenes.
MT1 Elimination Reactions 3— Learning Goals: Propose mechanisms for elimination reactions. Predict the products and specify the reagents for alkyne synthesis for elimination reactions. Differentiate between E2 and E1 reactions. Describe the stereochemistry the stereochemistry for E2 and E1 reactions as they relate to alkenes.
Alkene Addition Reactions— Learning Goals: Describe the reacts and reagents necessary to conduct an alkene addition reaction. Elucidate alkene addition reactions with electron-pushing arrow flow. Describe the role of acid catalyst in the presence of nucleophile and alkene. Predict the products and specify the reagents for alkene addition reactions. Differentiate Markovnikov addition vs anti-markovnikov addition. Differentiate addition reactions including Markovnikov, hydration, hydrogenation, and halogenation of alkenes.
Properties of alkenes, E vs Z, E2 reactions, Markovnikov— Learning Goals: Prepare the transformation of alkenes from various starting materials. Define some key characteristics of alkenes. Distinguish E vs Z nomenclature. Describe relative acidities among pi bonds. Recall the use of SN2/SN1/E2 reactions and mechanisms. Recall the term antiperiplanar. Differentiate the terms markovnikov from antimarkovnikov
Alkenes reactions H2SO4 H2O and alcohol dehydration— Learning Goals: Differentiate nucleophile from electrophile. Predict the products using alkenes and acid and nucleophile. Utilize H@SO4 and H2O in predict the product reactions. Prepare alkenes from various sources. Differentiate acid acids and bases regarding alkene reactions. Compare and contrast different reagents such as E2 vs SN2 reactions.
MT1 Alkene review lecture HBr H2SO4 Oxymerc Hydroboration SQ22— Learning Goals: BH3, THF, H2O2, NaOH, H2O; Hg(OAc)2, NaBH4, NaOH; HBr, dehydration of alcohols, mark vs antimark; Br2
Alkenes, HBr, Oxymercuration demercuration, Hydroboration, Br2—Learning goals: Conduct alkene reactions. Describe reactions using HX. Conduct alkene reactions utilizing terms such as markovnikov and antimarkovnikov. Critically evaluate carbocations. Determine when to rearrange a carbocation. Increase a ring in size to increase stability. Utilize resonance to determine regiochemistry. Predict the starting material. Predict the product. Use reagents such as PBr3. Prepare antimarkovnikov reactions using ROOR/ R202/ HOOH/ H202 reagents. Propose mechanisms for radical halogenation mechanisms. Provide a complete curved-arrow mechanism for oxymercuration-demercuration reactions. Provide a complete curved-arrow mechanism for hydroboration oxidation reactions. Reduce alkenes using H2, PT-C (or Pd/C, Pt/C, etc). Prepare hydrogenation reactions. Conduct alkene addition reactions. Prepare epoxide via Syn addition followed by anti-addition of 2 halogens
MT1 Alkenes, E2, Hydrogenation, Hydration of alkenes, Mark vs. Antimark— Learning Goals: Reagents: NaOC2H5, HOC2H5; H2, Pd; D2, Pt-C; Alkene + acid catalyst; Hydride shift; HX vs HX in ROOR; Reactions of alkenes.
MT1 Alkenes, HBr, Br2, Mark vs Antimark, Syn vs Anti + NMR review— Learning Goals: Reactions of alkenes, alkene addition reactions, and NMR Review
MT1 Alkenes Review, Markovnikov vs antimarkovnikov, HBr and H2O— Learning Goals: Learning outcomes: Describe the reacts and reagents necessary to conduct alkene addition reactions. Elucidate alkene addition reactions with electron-pushing arrow flow. Describe the role of acid catalyst in the presence of nucleophile and alkene. Predict the products and specify the reagents for alkene addition reactions. Differentiate markovnikov vs anti-markovnikov addition. Compare and contrast HBr from Br2 reactions. Differentiate addition reactions including markovnikov, hydration, hydrogenation, and halogenation of alkenes. Differentiate oxymercuration demercuration from hydroboration oxidation. Apply the terms markovnikov and anti-markovnikov addition to oxymercuration demercuration and hydroboration oxidation.
Alkenes, Br2, epoxides, ozonolysis, alkynes— Learning goals: Conduct alkene reactions. Predict the reagents when given the reactants and products. Distinguish more substituted from less substituted sides of epoxide. Prepare reactions using X2. Utilize terms such as markovnikov and antimarkovnikov with alkenes. Describe the role of MCPBA with alkene reactions. Distinguish syn and anti-reactions with alkenes. Prepare ring-opening reactions of epoxides. Create syn vicinal diol alcohols from alkene. Utilize syn reagants such as OsO4. Conduct oxidative cleavage reactions using O3 (Ozonolysis). Recall Br2, hv reactions. Prepare alkyne formation products. Propose the reagents for synthesis reactions. Describe NaNH2 and its role in alkyne formation. Add R groups to terminal alkynes
Alkenes and alkyne review session, carbenes, hydrolysis of alkynes— Learning goals: Conduct synthesis problems involving alkenes and alkynes. Utilize reagents such as NaNH2, NH3 (liquid). Utilize reagents such as Br2, hv. Utilize reagents such as LDA. Utilize reagents such as Br2, CCl4. Utilize reagents such as H3O+ workup. Utilize epoxides to create alcohols during synthesis problems. Prepare carbenes in organic reactions. Utilize alkenes with carbenes to conduct organic reactions. Utilize reagents such as CH2NH2. Describe the role of diazomethane with alkenes. Describe the role of halogenated carbenes with alkenes. Utilize reagents such as HCX3, KOC(CH3)3. Describe the role of the Simmon Smith reagent. Utilize reagents such as CH2I2, CuZn. Utilize a variety of reagents to create epoxides from alkenes. Describe the role of with NaNH2, NH3 (liquid) to create alkenes and alkynes. Differentiate internal alkynes and terminal alkynes. Utilize reagents such as NaOCH2CH3, HOCH2CH3. Utilize reagents such as tert-butoxide. Utilize reagents such as H2SO4. Describe the role of the benzylic carbon. Conduct oxidative cleavage reactions using O3 (Ozonolysis). Describe the role of epoxide intermediates to create an anti-relationship. Describe the role of H2, Pd while reducing alkenes or alkynes. Describe the role of H2, Lindlar catalyst while reducing alkynes. Describe the role of Li, NH3 (liquid) while reducing alkynes. Differentiate cis vs trans and E vs Z while conducting reduction of alkynes. Conduct halogenation with alkyne reactions. Differentiate markovnikov from anti-markovnikov with alkynes. Conduct hydrolysis and hydration reactions with alkynes. Describe the role of enol-keto tautomerization. Define the steps necessary to transform alkynes to aldehydes. Define the steps necessary to transform alkynes to ketones.
NMR of alkenes, allylics, alkynes and benzenes, and alkyne reactions— Learning Goals: Learning goals: Describe the role of NMR in organic chemistry. Define the key characteristics of the X and Y axes of the NMR graph. Differentiate peaks from neighbors on the NMR data. Distinguish H-NMR from C-NMR. Draw a molecule based on the data provided on the NMR. Distinguish down-field from up-field. Describe the role of electronegativity on the NMR data. Define DOU and its importance in NMR. Review triple bond synthesis. Review reagents necessary to conduct reactions of alkynes.
MT1 Alkenes Modern Sonogashira Suzuki Heck Synthesis problem Ozonolysis— Learning Goals: The Sonogashira reaction (also called the Sonogashira-Hagihara reaction) is the cross coupling of aryl or vinyl halides with terminal alkynes to generate conjugated enynes and arylalkynes. The reaction typically proceeds in the presence of a palladiu catalyst, a copper(I) cocatalyst, and an imine base.
MT1 CHE 118B Harvard Review #1 Alkene Reactions Review Session— Learning Goals: Describe the reacts and reagents necessary to conduct alkene reactions. Differentiate terms such as saturated vs unsaturated hydrocarbon. Compare and contrast terminal and internal alkenes. Elucidate alkene reactions with electron-pushing arrow flow. Predict the products and specify the reagents for alkene reactions. Differentiate Zaytsev from Hoffman. Distinguish syn from anti stereochemistry. Describe the mechanism for SN2 reactions. Describe the mechanism for E2 reactions. Describe the mechanism for E1 reactions. Define racemic mixture and its relation to stereochemistry. Prepare an organic chemistry alkene reaction using reagents such as H2, Pd/C. Prepare an organic chemistry alkene reaction using reagents such as Hg(OAc)2, H20, NaBH4. Prepare an organic chemistry alkene reaction using reagents such as BH3, THF.
MT1 Harvard Review #2A Alkenes— Learning outcomes: Describe the reacts and reagents necessary to conduct alkene reactions. Elucidate alkene reactions with electron-pushing arrow flow. Predict the products and specify the reagents for alkene reactions. Distinguish syn from anti stereochemistry. Define racemic mixture and its relation to stereochemistry. Prepare an organic chemistry alkene reaction using reagents such as Hg(OAc)2, H20, NaBH4. Prepare an organic chemistry alkene reaction using reagents such as BH3, THF. Prepare an organic chemistry alkene reaction using reagents such as HCl. Prepare an organic chemistry alkene reaction using reagents such as Br2. Prepare an organic chemistry alkene reaction using reagents such as Br2, ROH. Prepare an organic chemistry alkene reaction using reagents such as H2O, H+. Prepare an organic chemistry alkene reaction using reagents such as O3, (CH3)2S. Prepare an organic chemistry alkene reaction using reagents such as MCPBA.
MT1 Harvard Review #2B Alkenes Reactions Review Session— Learning Goals: Describe the reacts and reagents necessary to conduct alkene reactions. Elucidate alkene reactions with electron-pushing arrow flow. Predict the products and specify the reagents for alkene reactions. Distinguish syn from anti stereochemistry. Define racemic mixture and its relation to stereochemistry. Prepare an organic chemistry alkene reaction using reagents such as Hg(OAc)2, H20, NaBH4. Prepare an organic chemistry alkene reaction using reagents such as BH3, THF. Prepare an organic chemistry alkene reaction using reagents such as HCl. Prepare an organic chemistry alkene reaction using reagents such as Br2. Prepare an organic chemistry alkene reaction using reagents such as Br2, ROH. Prepare an organic chemistry alkene reaction using reagents such as H2O, H+
MT1 CHE 118B Review Session— Learning Goals: Comprehensive review of all alkene reactions. Reagents include H2, Pd; Carbenes, KOH, CHI3, Simmon Smith; Br2; Addition of alcohols, Dehydration of alcohols, mark vs antimark, BH3, THF; Oxymerc demerc; hydroboration oxidation
MT1 CHE 118B Review Session 2nd Version— Learning Goals: Comprehensive review of all alkene reactions. Reagents include H2, Pd; Carbenes, KOH, CHI3, Simmon Smith; Br2; Addition of alcohols, Dehydration of alcohols, mark vs antimark, BH3, THF; Oxymerc demerc; hydroboration oxidation
Alkyne Review Session Practice Exam Rapid Review— Learning Goals: Utilize reagents and prepare reactions such as: NaNH2, NH3; Br2; H2O2, NaOH; Terminal alkyne reactions, internal alkyne reactions; Hg2+, H+, H2O; acid work up with triple bond; HBr with peroxide; enolization
Alkynes and Allylics Practice Exam Review Session— Learning Goals: Conduct reactions such as: alkyne reactions and allylic reactions. Use reagents such as H2 in Lindlar; NBS, CCl4; Allylic grignard and epoxide;
ch13 ch14 alkynes and allylics intensive version 1— Learning Goals: Conduct intensive reactions using allylics and Diels Alder
ch13 ch14 alkynes and allylics intensive— Learning Goals: Conduct intensive reactions and synthesis problems using allylics, diels alder, alkynes, and more.
CHE 118B Allylics_Alkynes— Learning Goals: Recognize when conjugation applies, how it impacts chemical stability, and use it to predict and rank stabilities of various substances. Predict and rank how various reactions and their reaction rates are impacted by conjugation/resonance, whether in a reactant or an intermediate or a product, for example in SN1 reactions, radical reactions or acid-base reactions. Predict the products of hydrogen halide additions to conjugated dienes. Identify 1,2 vs 1,4 addition products in hydrogen halide additions to conjugated dienes. Identify thermodynamic versus kinetic products. Predict the products of allylic radical bromination reactions. Draw mechanisms for addition reactions or SN1 reactions proceeding through allylic cations. Draw resonance structures for allylic cations, radicals, or anions. Predict the products of Diels-Alder reactions, including stereochemistry; and when the dienophile is disubstituted. Identify reactants involved in Diels-Alder reactions, allylic bromination reactions, and hydrogen halide additions to conjugated dienes
MT2 Allylics and diels alder reactions— Learning Goals: Identify conjugation and conjugated systems; recognize isolated and conjugated double bonds. Identify systems that require representation with resonance structures. Be able to draw resonance structures of allylic carbocations and explain their stability. Describe the hybridization and geometry of systems with electron delocalization. Describe conjugated dienes, their stability and their properties, including bond lengths and molecular geometry. Be able to work with molecular orbital diagrams for conjugated π-systems. Be able to predict the products of electrophilic addition to dienes–1,2- versus 1,4-addition and to write the reaction mechanisms. Differentiate kinetic versus thermodynamic products and explain the products formed under specified reaction conditions. Identify Diels-Alder reactions; be able to write the reaction mechanism. Apply the rules governing Diels-Alder reaction including the rule of endo-addition. Perform retrosynthetic analysis of a Diels-Alder product. Explain the relationship of conjugated polyenes and light. Apply the nomenclature associated with the classes of compounds in this chapter.
Fast paced ortho para meta benzene aromatic session— Learning Goals: At the end of this chapter, students will able to: Describe the hybridization of benzene. Describe the resonance structures of benzene. Recognize the general properties of aromatic compounds, the criteria of aromaticity, and Huckel’s rule. Recognize the methods for naming aromatic compounds, including IUPAC method and common names. Know the types of electrophilic aromatic substitution reactions. Compare and contrast the reactivity of aromatic compounds and orientation of monosubstituted benzene reactions. Predict the products of alkyl side chains of aromatic compounds. Recognize and distinguish between aromatic and antiaromatic compounds by their structures. Describe the properties of aromatic and antiaromatic compounds, and the chemical consequences of aromaticity. Recognize and be able to write the mechanism of electrophilic aromatic substitution. Be able to outline the completed electrophilic aromatic substitution reactions of the following types: halogenation, nitration, sulfonation, and Friedel-Crafts acylation & alkylation.
NBS Diels alder Thermodynamic vs kinetic products allylics + triple bond alkyne content— Learning Goals: Identify conjugation and conjugated systems; recognize isolated and conjugated double bonds. Identify systems that require representation with resonance structures. Be able to draw resonance structures of allylic carbocations and explain their stability. Describe the hybridization and geometry of systems with electron delocalization. Describe conjugated dienes, their stability and their properties, including bond lengths and molecular geometry. Be able to work with molecular orbital diagrams for conjugated π-systems. Be able to predict the products of electrophilic addition to dienes–1,2- versus 1,4-addition and to write the reaction mechanisms. Differentiate kinetic versus thermodynamic products and explain the products formed under specified reaction conditions. Identify Diels-Alder reactions; be able to write the reaction mechanism. Apply the rules governing Diels-Alder reaction including the rule of endo-addition. Perform retrosynthetic analysis of a Diels-Alder product. Explain the relationship of conjugated polyenes and light. Apply the nomenclature associated with the classes of compounds in this chapter.
NBS Diels alder Thermodynamic vs kinetic products with EMPHASIS on allylics and diels alder— Learning Goals: Identify conjugation and conjugated systems; recognize isolated and conjugated double bonds. Identify systems that require representation with resonance structures. Be able to draw resonance structures of allylic carbocations and explain their stability. Describe the hybridization and geometry of systems with electron delocalization. Describe conjugated dienes, their stability and their properties, including bond lengths and molecular geometry. Be able to work with molecular orbital diagrams for conjugated π-systems. Be able to predict the products of electrophilic addition to dienes–1,2- versus 1,4-addition and to write the reaction mechanisms. Differentiate kinetic versus thermodynamic products and explain the products formed under specified reaction conditions. Identify Diels-Alder reactions; be able to write the reaction mechanism. Apply the rules governing Diels-Alder reaction including the rule of endo-addition. Perform retrosynthetic analysis of a Diels-Alder product. Explain the relationship of conjugated polyenes and light. Apply the nomenclature associated with the classes of compounds in this chapter.
Ortho para meta benzene reactions— Learning Goals: At the end of this chapter, students will able to: Describe the hybridization of benzene. Describe the resonance structures of benzene. Recognize the general properties of aromatic compounds, the criteria of aromaticity, and Huckel’s rule. Recognize the methods for naming aromatic compounds, including IUPAC method and common names. Know the types of electrophilic aromatic substitution reactions. Compare and contrast the reactivity of aromatic compounds and orientation of monosubstituted benzene reactions. Predict the products of alkyl side chains of aromatic compounds. Recognize and distinguish between aromatic and antiaromatic compounds by their structures. Describe the properties of aromatic and antiaromatic compounds, and the chemical consequences of aromaticity. Recognize and be able to write the mechanism of electrophilic aromatic substitution. Be able to outline the completed electrophilic aromatic substitution reactions of the following types: halogenation, nitration, sulfonation, and Friedel-Crafts acylation & alkylation.
Rapid review benzene rings and directing effects— Learning Goals: At the end of this chapter, students will able to: Describe the hybridization of benzene. Describe the resonance structures of benzene. Recognize the general properties of aromatic compounds, the criteria of aromaticity, and Huckel’s rule. Recognize the methods for naming aromatic compounds, including IUPAC method and common names. Know the types of electrophilic aromatic substitution reactions. Compare and contrast the reactivity of aromatic compounds and orientation of monosubstituted benzene reactions. Predict the products of alkyl side chains of aromatic compounds. Recognize and distinguish between aromatic and antiaromatic compounds by their structures. Describe the properties of aromatic and antiaromatic compounds, and the chemical consequences of aromaticity. Recognize and be able to write the mechanism of electrophilic aromatic substitution. Be able to outline the completed electrophilic aromatic substitution reactions of the following types: halogenation, nitration, sulfonation, and Friedel-Crafts acylation & alkylation.— Learning Goals: At the end of this chapter, students will able to: Describe the hybridization of benzene. Describe the resonance structures of benzene. Recognize the general properties of aromatic compounds, the criteria of aromaticity, and Huckel’s rule. Recognize the methods for naming aromatic compounds, including IUPAC method and common names. Know the types of electrophilic aromatic substitution reactions. Compare and contrast the reactivity of aromatic compounds and orientation of monosubstituted benzene reactions. Predict the products of alkyl side chains of aromatic compounds. Recognize and distinguish between aromatic and antiaromatic compounds by their structures. Describe the properties of aromatic and antiaromatic compounds, and the chemical consequences of aromaticity. Recognize and be able to write the mechanism of electrophilic aromatic substitution. Be able to outline the completed electrophilic aromatic substitution reactions of the following types: halogenation, nitration, sulfonation, and Friedel-Crafts acylation & alkylation.
Allylics, conjugated systems, 1,2 vs 1,4 systems, kinetic vs. thermodynamic products, diels alder— Learning Goals: Learning goals: Describe the role of the allylic carbon. Describe the importance of the allylic carbon. Describe the acidity vs basicity of the allylic carbon. Describe the role of the benzylic carbon. Define conjugation. Conduct allylic reactions with LDA. Critically evaluate the role of strong bases with acid compounds to conduct reactions. Utilize Grignard reactions with allylic carbons. Utilize organometallic reactions with allyic carbons. Utilize NBS, hv to further conduct allylic reactions. Conduct SN2 and SN1 reactions at the allylic carbon. Recall the limitations of SN1. Identify appropriate SN1 leaving groups for aliphatic and allylic reactions. Distinguish kinetic from thermodynamic products. Differentiate 1,2 reactions from 1,4 reactions. Define the role of temperature when comparing thermodynamic and kinetic reactions. Compare stability for kinetic and thermodynamic products. Illustrate the importance of resonance when conducting kinetic and thermodynamic reactions. Utilize reagents such as HBr with allylic compounds. Utilize reagents such as Br with allylic compounds. Describe the role of epoxide intermediates when conducting allylic reactions. Conduct diels alder reactions. Differentiate dienes from dienophiles. Describe stereochemistry and regiochemistry during diels alder reactions. Describe nucleophilicity vs electrophilicity when comparing dienes and dienophiles.
Huckel’s rule, aromaticity, benzene reactions, ortho para and meta— Learning Goals: Define the role of 4n + 2 rule to determine aromaticity. Define Huckel’s rule. Define aromaticity. Differentiate aromatic, non-aromatic, and anti-aromatic. Utilize Huckel’s rule to distinguish aromatic from anti-aromatic. Conduct reactions of benzene. Utilize a variety of reagents to conduct reactions such as halogenation, sulfonation, alkylation, acylation, and nitration with benzene rings. Predict the products with benzene rings. Draw the mechanisms with benzene ring reactions. Define the terms ortho, para, and meta. Describe how the terms ortho, para, and meta are involved in predicting the products with benzene reactions. Describe the regiochemistry when conducting benzene reactions. Utilize reagents such as HNO3, H2SO4. Utilize reagents such as H2SO4, SO3. Utilize reagents such as X2, FeX3. Utilize reagents such as RX, AlCl3. Utilize reagents such as RCOCl, AlCl3. Elucidate the lewis structures for atoms attached to the benzene ring. Differentiate electron withdrawing groups from electron donating groups attached to benzene rings. Describe the importance of electron withdrawing group and electron donating groups when predicting the products of benzene rings.
Aromatics: Sulfonation— Learning goals:
• Propose mechanisms for aromatic reactions
• Differentiate between aromatic reactions such as nitration, halogenation, sulfonation, and more
• Describe the stereochemistry and regiochemistry for aromatic reactions
• Elucidate the electron-pushing arrows for the sulfonation mechanism
Benzene ring reactions, ortho para meta, activators vs deactivators— Learning goals:
-Describe the role of ortho, para and meta when conducting reactions with benzene
-Utilize reagents such as HNO3, H2SO4
-Utilize reagents such as H2SO4, SO3
-Utilize reagents such as X2, FeX3
-Utilize reagents such as RX, AlCl3
-Utilize reagents such as RCOCl, AlCl3
-Describe the role of directors on the benzene ring. Define terms such as activating vs deactivating. Utilize terms such as electron withdrawing group vs electron donating group. Critically evaluate the role of carbocation rearrangement when conducting alkylation reactions with benzene rings. Differentiate alkylation from acylation reactions. Conduct multi-step predict the product with benzene reactions. Describe the limitations of Friedel craft alkylation and Friedel craft acylation. Describe the role of NH2 attached to a benzene to create a bulky director attached to the benzene ring. Identify para-only directors. Distinguish the role of MCPBA from Sn, HCl
Benzene ring exam review session, NBS, electrophilic aromatic substitution— Learning goals: Rank reactants from most reactive to least reactive toward electrophilic aromatic substitution reactions. Label compounds as either aromatic, anti-aromatic or non-aromatic. Distinguish electron donator groups from. Provide a detailed mechanism for acylation with benzene rings. Describe the limitations of Friedel craft acylation reactions. Describe the importance of activators and deactivators attached to benzene rings. Show how you effectively and efficiently make transformations using synthesis. Recall when to use Br2, hv. Recall when to use strong bases in organic chemistry reactions. Recall the importance of leaving groups. Recall when to use reagents such as NBS, hv. Recall how to create pi bonds in organic chemistry reactions. Compare relative strengths of bases and their importance in the context of benzene activating groups. Describe the effects of a bulky reagent attached to a benzene ring in benzene ring reactions. Conduct multi-step predict the product reaction problems with benzene rings. Recall the importance of strong bases and their effects on acidic atoms in organic chemistry reactions. Utilize a wolf kischner reagent when conducting benzene ring reactions. Recall a variety of reducing agents in the context of benzene ring reactions. Conduct nitration reactions with benzene rings. Conduct acylation reactions with benzene rings. Differentiate ortho and para directors vs meta directors. Distinguish activating from deactivating when working with benzene rings. Predict the reagents in the context of a benzene ring reaction. Predict the products in the context of a benzene ring reaction. Conduct a synthesis problem in the context of a benzene ring reaction.
Allylics, diels alder, benzene ring exam review session— Learning Goals: Learning goals: Describe the role of reagents such as NCS, hv. Describe the role of reagents such as Cl2 in diene reactions. Describe the role of reagents such as Grignard or other organometallics. Differentiate kinetic from thermodynamic products. Describe the role of temperature in organic chemistry reactions. Differentiate markovnikov from anti-markovnikoV. Demonstrate step-wise mechanism electron arrow flow for organic chemistry reactions. Predict the product in the context of dienes, allylic reactions, and benzene reactions. Illustrate SN2 reactions in the context of allylic reactions. Identify good leaving groups such as tosylates. Identify diels alder reactions. Distinguish diene from dienophile. Propose mechanism for diels alder reactions. Illustrate stereochemistry for diels alder reactions. Demonstrate regiochemistry spatial orientation with diels alder reactions. Locate sp3 stereocenters. Propose a mechanism for diene and allylic reactions. Describe the importance of acid in diene and allylic reactions. Recall various poor nucleophiles that can be used in diene and allylic reactions. Discuss the role of resonance in diene and allylic reactions. Solve radical reactions of NBS with allylic reactions. Compare relative stability of radicals. Devise the mechanism for a variety of allylic reactions. Define the role of 4n + 2 rule to determine aromaticity. Define Huckel’s rule. Define aromaticity. Differentiate aromatic, non-aromatic, and anti-aromatic. Utilize Huckel’s rule to distinguish aromatic from anti-aromatic. Compose a synthesis problem with bezene reactions and reagents. Transform NO2 to NH2 as different species on the benzene ring. Recall a variety of reducing agents in the context of benzene ring reactions. Conduct nitration reactions with benzene rings. Conduct acylation reactions with benzene rings. Differentiate ortho and para directors vs meta directors. Distinguish activating from deactivating when working with benzene rings. Predict the reagents in the context of a benzene ring reaction. Predict the products in the context of a benzene ring reaction. Conduct a synthesis problem in the context of a benzene ring reaction. Conduct a synthesis problem in the context of allylic reactions
Aldehydes ketones acetals ketals imines— Learning goals: -Propose mechanisms for hydration reactions in the context of ketones and aldehydes -Devise a mechanism for acetal and hemiacetal formation -Describe the importance of acid catalyst in the presence of ketones and aldehydes -Identify when to use resonance in acetal and hemiacetal formation reaction mechanisms -Distinguish acetals from hemiacetals -Propose mechanisms for ketals and hemiketals -Distinguish ketals from hemiketals -Identify various poor nucleophiles that could be used in the presence of acid catalyst and ketones and aldehydes -Prepare cyclic ketals and acetals -Utilize protecting groups in the context of aldehydes and ketones -Design a reaction to remove protecting groups from aldehydes and ketones -Conduct synthesis problems in the context of aldehydes and ketones -Formulate predict the product reactions using reducing agents -Prepare reactions using reducing reagents such as LiAlH4 OR NaBH4 -Describe when to use protecting groups in the context of aldehydes and ketones -Devise a ketal protecting group -Devise an acetal protecting group -Devise a thioketal protecting -Differentiate when to use acetal vs thioketal protecting groups -Describe how to remove protecting groups with H2, Raney-Ni -Recall the role of alkynes in the context of ketones and aldehydes -Illustrate the role of nitrogen in the context of ketones and aldheydes -Describe the formation of imines -Describe the formation of enamines -Differentiate primary, secondary and tertiary amines and their role in imine and enamine formation-Distinguish imines from enamines -State when a reaction is NO REACTION in the context of amines and ketones and aldehydes
Ketones and aldehydes reactions, acetals vs ketals— Learning goals:
-Elucidate the process of oxidation of alcohols
-Synthesize aldehydes and ketones
-Interpret PCC and Jones in oxidation reactions
-Conduct oxidative cleavage reactions using O3 (Ozonolysis)
-Recall the formation of ketones and aldehydes from triple bond (alkyne) intermediates
-Design synthesis problems in the context of creating aldehydes and ketones
-Oxidize allylic alcohols using a variety of reagents
-Describe the role of MnO2 during oxidation events
-Propose mechanisms for hydration reactions in the context of ketones and aldehydes
-Devise a mechanism for acetal and hemiacetal formation
-Describe the importance of acid catalyst in the presence of ketones and aldehydes
-Identify when to use resonance in acetal and hemiacetal formation reaction mechanisms
-Distinguish acetals from hemiacetals
-Propose mechanisms for ketals and hemiketals
-Distinguish ketals from hemiketals
-Identify various poor nucleophiles that could be used in the presence of acid catalyst and ketones and aldehydes
-Prepare cyclic ketals and acetals
Ketones and aldehydes reactions, acetals vs ketals, imines vs enamines— Learning goals: -Propose mechanisms for hydration reactions in the context of ketones and aldehydes -Devise a mechanism for acetal and hemiacetal formation -Describe the importance of acid catalyst in the presence of ketones and aldehydes -Identify when to use resonance in acetal and hemiacetal formation reaction mechanisms -Distinguish acetals from hemiacetals -Propose mechanisms for ketals and hemiketals -Distinguish ketals from hemiketals -Identify various poor nucleophiles that could be used in the presence of acid catalyst and ketones and aldehydes -Prepare cyclic ketals and acetals -Utilize protecting groups in the context of aldehydes and ketones -Design a reaction to remove protecting groups from aldehydes and ketones -Conduct synthesis problems in the context of aldehydes and ketones -Formulate predict the product reactions using reducing agents -Prepare reactions using reducing reagents such as LiAlH4 OR NaBH4 -Describe when to use protecting groups in the context of aldehydes and ketones -Devise a ketal protecting group -Devise an acetal protecting group -Devise a thioketal protecting -Differentiate when to use acetal vs thioketal protecting groups -Describe how to remove protecting groups with H2, Raney-Ni -Recall the role of alkynes in the context of ketones and aldehydes -Illustrate the role of nitrogen in the context of ketones and aldheydes -Describe the formation of imines -Describe the formation of enamines -Differentiate primary, secondary and tertiary amines and their role in imine and enamine formation -Distinguish imines from enamines -State when a reaction is NO REACTION in the context of amines and ketones and aldehydes
Aldehydes Ketones alpha carbon chemistry aldol— Learning Goals: Carbonyl Alpha Substitution Reactions. Draw general alpha carbon reaction mechanisms incorporating enols for neutral/acidic reactions and enolates for basic reactions. Draw basic and acidic tautomerizations. Determine if a kinetic or thermodynamic enolate will form, based on reaction conditions. Draw kinetic and thermodynamic enolate reaction mechanisms. Draw mechanisms for halogenation at alpha carbon. Draw mechanisms for direct enolate alkylation. Carbonyl Condensation Reactions, Draw aldol reaction mechanisms (Single reactant, crossed, directed, and intramolecular). Draw Claisen condensation mechanism (Single reactant and Crossed). Draw Intramolecular Claisen mechanism (Dieckmann cyclization). Draw sulfur analogue of Claisen condensation (as in acetyl CoA). Determine products of Michael type reactions.
Aldehydes Ketones wittig imine enamine— Learning Goals: Students will be able to evaluate and justify the relative reactivity of Aldehydes vs ketones 2. Students will be able to describe aldehydes and ketones via IUPAC nomenclature, and will be comfortable at identifying common-name ketones and aldehydes as described in the chapter. 3. Students will be able to predict the products of Nucleophilic addition reactions of aldehydes and ketones. (hydration, cyanohydrins, acetal, imine, enamine, Wittig reaction products) 4. Students will be able to determine the carbonyl starting material and reagent to make any of the listed products. 5 Students will be able to utilize the synthesis of acetal protecting groups.
Aldol condensation, Michael addition, Robinson annulation— Learning goals: -Devise an aldol condensation reaction mechanism -Utilize a strong base to deprotonate an acidic proton -Compare aldehydes and ketones in aldol condensation formation -Locate alpha protons -Interpret aldehydes and ketones to be used as electrophiles vs nucleophiles -Assemble an enolate ion -Recall the role of resonance in an organic chemistry reaction mechanism -Produce alpha, beta unsaturated alkenes from aldehydes and ketones -Conduct dehydration throughout aldol condensation reaction mechanisms -Compare relative acidities among alpha protons -Qualify the use epoxides in aldol condensation reaction mechanisms -Qualify the use of SN2 mechanisms in aldol condensation reaction mechanisms -Demonstrate the use of reducing agents in the presence of aldehydes and ketones -Devise mechanisms with the use of organometallic reactions in the presence of aldehydes and ketones -Defend the use of cuprate lithium (R2CuLi) reactions in the presence of Conjugated pi bond systems involving ketones and aldehydes -Differentiate 1,2 reactions vs 1,4 reactions in the presence of aldehydes and ketones -Illustrate Michael addition reactions -Elucidate mechanisms involving various condensation reactions -Distinguish Michael condensation from aldol condensation -Propose electron-pushing arrow mechanisms for aldol condensation and Michael additions -Perform intramolecular ring formations using aldol and Michael additions -Recognize acidic protons -Define Robinson Annulation -Differentiate aldol condensation, Michael addition and robinson annulation
Wittig, Wolf Kischner, Baeyer Villager, Aldol— Learning goals: • Define the role of the Wittig reaction •Transform ketone via Wittig reaction •Describe the limitations of Wittig reaction •List the key characteristics of the Wittig reaction •Recognize the role of a strong base in the Wittig reaction • Draw electron-pushing mechanism arrows with the Wittig reaction • Differentiate Wittig from Wolf Kischner •Identify the Wolf Kischner reaction and its reagents • Inspect the outcome of the Wolf kischner reaction •Identify the reagent NH2NH2, OH-, heat •Describe the transformation of ketone in the Baeyer Villager reaction •Describe the transformation of aldehyde in the Baeyer Villager reaction •Identify the reagents MCPBA and CF3CO3H •Interpret aldol condensation reagents and the reaction mechanism •Justify the use of resonance structures in aldol condensation • Describe the dehydration process in aldol condensation reactions •Recall the need for strong base in aldol condensation reactions •Demonstrate aldol condensation intramolecular ring formation • Compare relative stabilities of molecular compounds • Identify the alpha carbon relative to carbonyl species • Conduct reactions of the alpha carbon • Add new species to the alpha carbon •Incorporate epoxides with alpha carbon chemistry • Differentiate 1,2 reactions from 1,4 reactions • Describe the role of resonance involved in 1,2 and 1,4 reactions • Identify the reagent R2CuLi and its effect on 1,2 and 1,4 reactions • Differentiate various reagents involved in 1,2 and 1,4 reactions • Identify Michael acceptors and Michael donors • Differentiate aldol condensation, Michael addition and robinson annulation •Prepare a synthesis reaction using utilizing aldehyde protecting groups • Compare relative acidic beta-dicarbonyls
1.5 HOUR COMPREHENSIVE FINAL EXAM REVIEW SESSION— Aldol condensation, michael addition, robinson annulation, wittig, wolf kischner, alkynes, alpha carbon chemistry, carbonyls, ketones, aldehydes, baeyer villager oxidation, CF3COOOH, migratory aptitude, MCPBA, and much more.
MT3 Quarter 2 CHE 118B Final Exam Review Session March 2022—Learning objectives: •Write a chemical equation for a carbonyl condensation reaction. •Differentiate aldol condensation, from Michael addition and Robinson Annulation. •Define the role of the Wittig reaction •Transform ketone via Wittig reaction •Describe the limitations of Wittig reaction •List the key characteristics of the Wittig reaction •Recognize the role of a strong base in the Wittig reaction • Draw electron-pushing mechanism arrows with the Wittig reaction • Describe the transformation of ketone in the Baeyer Villager reaction •Describe the transformation of aldehyde in the Baeyer Villager reaction •Identify the reagents MCPBA and CF3CO3H •Interpret aldol condensation reagents and the reaction mechanism •Justify the use of resonance structures in aldol condensation • Describe the dehydration process in aldol condensation reactions •Recall the need for strong base in aldol condensation reactions •Demonstrate aldol condensation intramolecular ring formation •Compare relative stabilities of molecular compounds •Identify the alpha carbon relative to carbonyl species •Conduct reactions of the alpha carbon • Add new species to the alpha carbon •Incorporate epoxides with alpha carbon chemistry • Differentiate 1,2 reactions from 1,4 reactions • Describe the role of resonance involved in 1,2 and 1,4 reactions • Identify the reagent R2CuLi and its effect on 1,2 and 1,4 reactions • Differentiate various reagents involved in 1,2 and 1,4 reactions • Identify Michael acceptors and Michael donors •Differentiate aldol condensation, Michael addition and robinson annulation •Prepare a synthesis reaction using utilizing aldehyde protecting groups • Compare relative acidic beta-dicarbonyls
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QUARTER 3 VIDEO HUB
Carboxylic acids, trends, acidity, and reactions problem solving session— Learning Goals: •Differentiate carboxylic acids and their derivatives •Predict the products using carboxylic acid and their derivatives •Utilize acyl chlorides in reactions •Prepare amide products in reactions •Differentiate acid acids and bases regarding carboxylic acid •Compare and contrast acids and bases regarding carboxylic acids
Carboxylic acids intro trends synthesis practice problem solving session— Learning Goals: •Differentiate carboxylic acids and their derivatives •Predict the products using carboxylic acid and their derivatives •Utilize acyl chlorides in reactions •Prepare amide products in reactions •Differentiate acid acids and bases regarding carboxylic acid •Compare and contrast acids and bases regarding carboxylic acids
Carboxylic acid formation acidity and basicity predict the product and synthesis problems— Learning Goals: •Differentiate carboxylic acids and their derivatives •Prepare carboxylic acids using a variety of reagents •Identify Grignard reactions •Identify the role of CN in carboxylic acid formation •Differentiate the reagent HCN from KCN •Discern acidity and basicity for carboxylic acids and their derivatives •Predict the products using carboxylic acid and their derivatives •Utilize acyl chlorides in reactions •Prepare acyl chloride products in reactions •Formulate synthesis problems and their intermediates
Carboxylic acid derivatives KMnO4 SOCl2 Esters anhydrides amides and nitriles— Learning Goals: •Identify the role of carboxylic acids in derivative questions • Differentiate the reagent SOCl2 from KmnO4 •Discern acidity and basicity for carboxylic acids derivatives and their relative reactivities •Predict the products using carboxylic acid and their derivatives •Utilize acyl chlorides in reactions •Prepare acyl chloride products in reactions •Formulate synthesis problems and their intermediates •Prepare products using intra-molecular ring formation. Identify reagents that create esters, anhydrides, acyl chlorides, and amides •Describe the mechanism of anhydride formation •Distinguish the carboxylic acid derivatives from one another.
Carboxylic acid and derivative review session winter 2022— Learning Goals: 1. Recognize the general structures of carboxylic acids, acyl halides, acid anhydrides, esters, amides, and nitriles, and be able to assign names to simple members of these compound families. 2. Identify and be able to write the general mechanism for nucleophilic acyl substitution, and be able to judge the relative reactivities of carbonyl compounds in this reaction. 3. Identify and be able to write the mechanisms for nucleophilic substitutions of acyl halides, and esters. 4. Identify and be able to write the mechanism for the acid-catalyzed hydrolysis of an ester and of a nitrile. 5. Identify and be able to write the mechanism for the hydroxide-promoted hydrolysis of an ester. 6. Identify and be able to write the mechanisms for the acid-catalyzed and the hydroxide-promoted hydrolysis of amides. 7. Identify and be able to write the mechanism for the Fischer esterification of a carboxylic acid. 8. Be able to describe how to use chemical reagents for the desired transformation among acid derivatives.
Carboxylic acids and their derivatives— Learning goals : • Identify the functional group and structure of a carboxylic acid •Compare relative acidities among various functional groups including carboxylic acids •Describe the general properties of carboxylic acids •Illustrate carboxylic acid resonance structures •Distinguish good bases from good acids •Elucidate the general mechanism for nucleophilic acyl substitution •Compare the relative reactivities of carbonyl compounds • Draw the mechanisms for nucleophilic substitutions of carboxylic acids •Construct carboxylic acids from various starting materials •Distinguish PCC from Jones •Utilize KMnO4 •Evaluate synthesis problems involving carboxylic acids •Describe the output of carboxylic acids •Describe the use of reagents such as LiAlH4 •Prepare the transformation of alcohol from carboxylic acid •Prepare the transformation of ester from carboxylic acid •Prepare the transformation of acyl chloride from carboxylic acid •Explain the importance of acyl chlorides •Prepare the transformation of anhydride from carboxylic acid •Prepare the transformation of amide from carboxylic acid •Identify HVZ reaction and its reagents •Describe the process of creating an alpha halogenate •Demonstrate intra-molecular ring formation with carboxylic acids and their derivatives
Carboxylic acids and their derivatives, DIBAL, R2CuLi— Learning goals: • Describe the role of acid-base interactions involved in carboxylic acid reactions • Differentiate carboxylic acid derivatives and their relationship to the term electrophilicity • Distinguish acids from bases in carboxylic acid derivatives • Identify resonance contributors among carboxylic acid derivatives • Compare electrophilicity among carboxylic acid derivatives • Differentiate increased reactivity among carboxylic acids and their derivatives • Identify the functional group and structure of a carboxylic acid • Compare relative acidities among various functional groups including carboxylic acids • Describe the general properties of carboxylic acids • Illustrate carboxylic acid resonance structures • Distinguish good bases from good acids • Elucidate the general mechanism for nucleophilic acyl substitution • Compare the relative reactivities of carbonyl compounds • Draw the mechanisms for nucleophilic substitutions of carboxylic acids • Construct carboxylic acids from various starting materials • Evaluate synthesis problems involving carboxylic acids • Describe the output of carboxylic acids • Describe the use of reagents such as LiAlH4 • Prepare the transformation of alcohol from acyl chloride • Prepare the transformation of ester from acyl chloride • Prepare the transformation of acyl chloride from acyl chloride • Explain the importance of acyl chloride • Propose the mechanism for R2CuLi in diethyl ether • Prepare the transformation of ketone from acyl chloride • Draw the structure of DIBAL and describe its role with acyl chloride • Prepare the transformation of amide from acyl chloride • List the reasons why amides have fewer reactions compared to other carboxylic acid derivatives • Prepare the transformation of alcohol from anhydride • Prepare the transformation of ester from anhydride • Explain the importance of anhydride • Prepare the transformation of ketone from anhydride • Draw the structure of DIBAL and describe its role with anhydride • Prepare the transformation of ketone from anhydride • Prepare the transformation of amide from anhydride • Prepare the transformation of tylenol from anhydride • Prepare the transformation of aspirin from anhydride • Prepare the transformation of alcohol from ester • Prepare the transformation of ester from ester • Draw the structure of DIBAL and describe its role with ester • Prepare the transformation of amide from ester • Describe the process of alpha alkylation relative to an ester • Prepare the transformation of carboxylic acid from amide • Prepare the transformation of ester from amide (indirectly) • Draw the structure of DIBAL and describe its role with amide • Prepare the transformation of amine from amide • Describe the process of hoffman rearrangement relative to an amide • Draw flow charts for carboxylic acids and carboxylic acid derivatives.
Carboxylic acid and derivatives practice review session 1— Learning goals:
• Describe reagents such as KCN, DMSO
• Describe reagents such as SOCl2, pyridine
• Describe the hydrolysis of cyanide
• Describe the transformation of anhydride to acyl chloride
• Describe reagents such as KMnO4, H2O, H+
• Describe reagents such as Br2, hv
• Describe reagents such as LiAl[OC(CH2CH3)3]H, diethyl ether
• Describe reagents such as [(CH3CH2)2CHCH2]2AlH
• Propose synthesis problems involving esters, aldehydes, and ring-opening
• Evaluate protecting groups in carboxylic acid and aldehyde reactions
• Describe reagents such as MCPBA with aldehydes and ketones
• Describe reagents using Baeyer-Villager oxidation
• Define the term migratory aptitude
• Describe reagents using R2CuLi, diethyl ether
• Describe reagents using Br2,PBr3
• Identify HVZ reaction and its reagents
• Describe the process of alpha bromination
• Propose synthesis problems involving carboxylic acid derivatives and amines
• Demonstrate the use of reducing agents in the context of carboxylic acids and their derivatives
• Recall the use of stereochemistry from SN2 and its role in carboxylic acid reactions and their derivatives
• Demonstrate output of amides with Hoffman rearrangement
Carboxylic acid and derivatives practice review session 2— Learning goals:
• Complete the predict the product reaction using R-Li
• Prepare the transformation of alcohol from anhydride
• Appraise carboxylic acid in basic conditions
• Evaluate carboxylate ion in haloalkane conditions
• Employ cuprate lithium (R2CuLi) in ester conditions
• Explain the result of ester with strong base
• Describe the process of alpha-alkylation
• Compose a reaction using a carbanion and epoxide
• Describe the formation of amide
• Distinguish carboxylic acid from carboxylate ion as a final product
• Describe reagents using SOCl2
• Describe the transformation of product using two carboxylic acids
• Prepare the esterification mechanism and product
• Describe the reaction of ester in C2H5OH and H2SO4 conditions
• Describe the reagent HCN with a 1,2 vs 1,4 scenario
• Describe the formation of cyanohydrin
• Identify the conditions necessary for HVZ
• Identify enol and enolates
• Describe the process of keto-enol tautomerization
• Describe the hydrolysis of cyanide/nitrile
Amines basicity amide formation imines and imine synthesis—
SOCl2 Cuprate Lithium DIBAL Carboxylic acid derivatives—
Amines exhaustive methylation gabriel synthesis nitrile amide and imine—
Amine basicity amide anhydride KCN and more—
Amines reactions, Hoffman rearrangement, Gabriel synthesis, exhaustive methylation—Learning goals:
• Recall carboxylic acid and derivatives reactions
• Identify amide functional group
• Differentiate amide from amine functional groups
• Devise reactions involving amines
• Compare relative basicities among amine groups
• Define the term induction
• Recall Hoffman rearrangement
• Predict the product using exhaustive methylation
• Recall reduction of amide
• Recall the use of imine formation
• Recall the use of enamine formation
• Transform a ketone with amine and NaBH3CN
• Describe azide reduction
• Recall the use of KMnO4 reagents with benzene
• Demonstrate the Gabriel synthesis mechanism
• Categorize the use of K2CO3
• Predict the formation of alpha, beta unsaturated alkenes
• Differentiate more substituted from least substituted regions during exhaustive methylation and Hoffman elimination reactions
Nitrous benzenes arene diazonium salts and phenols—
Mannich, Diazonium nitrogen, nitrous amines, benzene amines—Learning goals:
• Identify Mannich reaction
• Describe the role of amino alkylation
• Choose the most acidic alpha proton in a Mannich reaction
• Differentiate nucleophile from electrophile in a Mannich reaction
• Differentiate amide, amine, imine, iminium ion, and enamine
• Differentiate carbonyl groups in a Mannich reaction
• Describe the role of the reagent NaHCO3
• Predict the product using ketone and aldehyde in a Mannich reaction
• Propose the mechanism of diazonium salt formation from aromatic amines
• Predict the product of the reactions of diazonium salts
• Create phenols from diazonium salts
• Describe the formation of N2+ and its role in producing new products
• Defend the importance of N2+ in reactions of diazonium salts
• Recall benzene reactions including halogenation, nitration, sulfonation, alkylation, acylation and more
• Differentiate the reagents MCPBA vs. Sn.HCl
• Identify Sandmeyer reactions
• Transform aryl diazonium salts with CuCl, CuBr and CuCN during Sandmeyer reactions
• Propose the mechanism for formation of nitrosonium ion from HNO2
• Classify various reagents in N2+ reactions
• Illustrate the formation of diazonium ions
• Identify the reagents necessary to create a phenol
• Describe how to create an empty benzene ring from a nitrous benzene ring
• Describe the result of phenol in basic NaOH conditions
• Define acidity of phenol
Nitrous amines, diazonium nitrogen, benzene amines, phenol, claissen rearrangement, Kolbe— Learning goals:
• Distinguish various nitrous amines reactions
• Describe the output of phenol reactions
• Differentiate between C- reactions from O- reactions
• Predict the product using poly-halogenation
• Recall terms such as ortho, para and meta
• Differentiate protic from aprotic conditions
• Define the use of Jones reagent in phenol reactions
• Classify oxidation and reduction in phenol reactions
• Prioritize reforming benzene rings and phenols in terms of stability
• Recall the term keto-enol tautomerization
• Label resonance structures with phenoxide intermediates
• Compare and contrast phenoxide and alpha carbanion reactions
• Draw a road map for phenol output based on the reagents provided
• Apply the term SN2 in a phenoxide context
• Distinguish ethers from esters in phenoxide reactions
• Prepare Claissen rearrangement reactions in the context of phenols and phenoxides
• Prepare Kolbe reactions
• Identify polymerization of phenol rings with formaldehyde in basic conditions
• Utilize keto-enol tautomerization in polymerization reactions
• Prepare synthesis reactions using benzene rings, phenols, and using terms such as ortho, para and meta
• Transform reactants using NaNO2, HCl, 0 degrees Celsius
Beta dicarbonyl claissen condensation reactions—
Claissen beta ketoesters robinson annulation and acyl anions heterocycle questions—
Amino acids, BOC, DCC, strecker, reactions, synthesis—
Benzylic carbon chemistry—
Benzylic carbon chemistry, MnO2; NBS, hv; Kmno4; nitrous amines; mannich, hoffman elimination; benzyne; Gabriel, imines, and beyond—
Claissen condensation, beta dicarbonyls, intramolecular aldol condensation, Robinson annulation, michael addition—
Robinson annulation, michael additon, intro to carbohydrates, sugars, glucose, mannose, fructose, fischer projections as it relates to carbohydrates, anomeric carbon, haworth projection, mutarotation, anomers, pyranose vs furanose, epimers, epimerization—
Sugars, carbohydrates, reducing sugar vs non-reducing sugars, Ruff degradation, HIO4, and more —
Proteins, N-C-C Backbone, pH vs pKa vs pI, isoelectric point, Gabriel, amino acid formation, strecker, BOC vs DCC, protecting groups and more—
Proteins, amino acids, edman degradation, sugars, carbohydrates, final exam review!—