Organic Chemistry 1

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Alkanes and Cycloalkanes

Welcome to organic chemistry! Start here with a deep dive into basic hydrocarbons: nomenclature, structure conventions, properties, and isomers. Work towards a deep understanding of the principles and skills that you will draw upon for the entire course.

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Nomenclature and Properties

Practice identifying the properties of alkanes and naming these compounds using the IUPAC nomenclature system.
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Isomers of Alkanes

Isomers are compounds with the same molecular formulas but different arrangements of atoms. Learn to identify isomeric alkanes and cycloalkanes.
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Sources and Uses of Alkanes

Where do alkanes come from and how are they used? Review the origins of these important compounds and their many applications.
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Newman Projections

Alkanes can rotate around the carbon-carbon single bonds in their structures, which leads to different conformations or three dimensional arrangements of the atoms. Draw alkane conformations using Newman projections.
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Ethane, Propane, and Butane

Conformational analysis of ethane, propane, and butane lays the groundwork for understanding conformations of more complicated organic compounds. Determine the most stable conformations of these compounds, and identify stereochemical relationships.
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Cycloalkanes and Cyclohexane

Practice identifying properties using IUPAC nomenclature and performing conformational analysis of substituted cyclohexanes and other cycloalkane molecules.
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Polycyclic Systems

Name fused and bridged polycyclic systems and indicate properties of these molecules.
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Stereoisomerism

Gain an understanding of the variation in spatial orientation of molecules. Build your visual-spatial intelligence through different projections and modeling conventions for organic chemicals. Explore an amazing world in which one small difference can make a chemical turn from a medicine to a toxin!

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Isomerism and Stereoisomerism

Isomers share the same chemical formula but differ in structure. Compare the differences between constitutional isomers, in which atoms are attached in different order, and stereoisomers, in which atoms are attached in the same order but arranged differently in space.
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Cahn-Ingold-Prelog System

A stereocenter is a portion of a molecule around which different arrangements in space produce different stereoisomers. Distinguish between different stereoisomers by assigning priorities to substituents at a stereocenter using the Cahn-Ingold-Prelog (CIP) system.
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Optical Activity

Compounds that have asymmetric structures rotate the plane of polarized light. Determine how this “optical rotation” is measured, what it signifies, and how it is conveyed in nomenclature.
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Enantiomers and Diastereomers

Differentiate between stereoisomers that are mirror images of each other (enantiomers) and those that are not (diastereomers).
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Symmetry and Chirality

Analyze whether a molecular structure is symmetric or chiral, a unique arrangement of substituents.
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Fischer Projections

Draw and interpret compounds with multiple chiral centers using Fischer projections.
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Conformationally Mobile Systems

Learn about stereoisomers that are formed by rotating around single bonds, and how they differ.
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Chemical Reactivity and Mechanisms

Discover the basic principles that explain why reactions occur between organic compounds. Learn how to predict and depict basic patterns in chemical reactivity and why organic chemists obsess about arrows!

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Energy Diagrams

Understand that the proposed mechanism of a chemical reaction requires knowledge of the structural and energy changes that occur as the reaction proceeds. Depict these changes using energy diagrams, which illustrate the various species that exist along the path of the reaction and their relative energy.
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Nucleophiles and Electrophiles

Delve into how majority of organic chemical reactions, polar reactions, involve the interaction of charged and/or polar species through the attraction of opposite charges.
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Mechanisms and Arrows

Interpret how chemical reactions occur as electrons undergo a reorganization among the species involved in the reaction. The depiction of this reorganization is referred to as a reaction mechanism; it is customary to use ‘curved arrows’ to represent the migration of electrons from their source toward their final position as a chemical reaction proceeds.
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Carbocations

Conquer carbocations, the organic species that has an electron-deficient carbon atom with a net positive charge. They are among the most common and strongest electrophiles involved in organic chemical reactions.
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Radical Reactions

Discover radicals, a very reactive electron-deficient species carrying a single electron. Most organic chemical reactions involve the reorganization of electrons in pairs, but an important subcategory of organic reactions involves the reorganization of single electrons among the reacting species, producing radicals.
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Acids and Bases

Dig into the many organic chemical reactions that involve proton-transfer processes, which by nature are acid-base reactions. The chemical reactivity of many organic compounds can be correlated with their acid-base properties.
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Substitution Reactions

Dive deeper into reactions to specifically replace functional groups on an organic structure. Learn the key differences between $S_N1$ and $S_N2$ reactions and appropriately choose reactants, conditions, and catalysts to ensure the synthesis of a targeted product.

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Alkyl Halides and Organohalides

Understand the physical and chemical properties of alkyl halides as they relate to reactivity in substitution reactions.
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$S_N1$ Reactions

Learn the fundamental characteristics of the $S_N 1$ reaction mechanism, including stereochemistry, carbocation rearrangements, and optimal reaction conditions.
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$S_N2$ Reactions

Determine the fundamental characteristics of the $S_N 2$ reaction mechanism, including stereochemistry, relative nucleophilicity, and optimal reaction conditions.
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Functional Group Transformations

Investigate the utility and strategic use of substitution reactions in synthesis, particularly in fundamental functional group conversion.
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Elimination Reactions of Alkenes

Explore an unsaturated hydrocarbon: the alkene. Learn about this class of compounds, nomenclature rules, properties, and how to synthesize them. Dig deeper to understand the reaction mechanisms underlying their synthesis and compare different routes to create them.

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Elimination Reactions and Alkenes

Familiarize yourself with the basics of eliminating a leaving group from a carbon atom and a hydrogen atom from a neighboring carbon atom to form a double bond between those two carbons (an alkene).
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Stereoisomerism and Stability

Dive into the stereochemical implications behind when an elimination reaction occurs, depending on the mechanism involved.
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The E2 Mechanism

Analyze the bimolecular elimination (E2) mechanism. This is the concerted (one step) reaction where all five atoms involved in the transformation must lie in the same two-dimensional plane and six electrons all move in one step, ending in an alkene.
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The E1 Mechanism

Practice various unimolecular elimination (E1) reactions, where the leaving group leaves in the rate determining step, forming a carbocation, and a beta-hydrogen is eliminated to form an alkene.
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Substitution Versus Elimination

Review the conditions that will allow you to predict whether a reaction will proceed via a substitution or an elimination pathway.
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Addition Reactions of Alkenes

With the new type of hydrocarbon, predict expected product outcomes when reacting alkenes in a variety of different types of reactions. Explore various methods that make alkenes excellent stepping stones to produce more complex structures.

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Addition Versus Elimination

Uncover how to add atoms or groups of atoms to each side of an alkene (the reverse of an elimination reaction), including syn and anti-additions as well as possible electrophiles that are used to react with the nucleophilic pi bond of the alkene.
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Hydrohalogenation

Conquer all aspects of the hydrohalogenation reaction, including the Markovnikov addition of a proton to form a carbocation, the carbocation rearrangement, and the formation of the alkyl halide.
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Acid-Catalyzed Hydration

Work on this reaction commonly learned as the first of three hydrations of an alkene. Acid-catalyzed hydration proceeds via Markovnikov addition, but allows for rearrangements of the carbon skeleton due to formation of a carbocation intermediate.
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Oxymercuration-Demercuration

Dissect the second of three hydrations of an alkene. Oxymercuration-demercuration allows for a Markovnikov addition of an alcohol (and a hydrogen atom in an anti-addition) to a double bond with no rearrangement possible.
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Hydroboration Oxidation

Work on the final hydration of an alkene. Hydroboration-oxidation allows for a syn anti-Markovnikov addition of an alcohol (and hydrogen) to an alkene with no rearrangements possible.
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Catalytic Hydrogenation

Master this transformation, the reduction of an alkene or alkyne (alkene to alkane OR alkyne to alkene/alkane). Based on the catalyst, you can predict the final product and stereochemical implications.
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Halogenation and Halohydrin Formation

Practice the halogenation reaction, which adds two halogen atoms in an anti-conformation on vicinal carbon atoms.
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Anti and Syn Dihydroxylation

Analyze the different conditions and outcomes of adding two alcohol groups vicinal on an alkene, forming 1,2-diols.
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Oxidative Cleavage

Learn how reacting alkenes with oxidizers forms ketones, carbon dioxide, and carboxylic acids or ketones and aldehydes. Oxidizing alkynes forms carboxylic acids and carbon dioxide.
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Products of Addition Reactions

After utilizing the various additions to alkenes, test your understanding of predicting mechanisms and products given reagents and conditions.
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Synthesis Strategies

Backwards plan from a product and design the synthesis of a given target molecule using a combination of the reactions you have learned up through addition reactions to double bonds (alkenes).
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Alkynes

An even greater degree of unsaturated hydrocarbon emerges: the alkyne. Learn about this classification of compound, nomenclature rules, properties, and how to synthesize them. Dig deeper to understand the reaction mechanisms underlying their use in synthesis, and ultimately learn why they hold a unique place in organic chemistry.

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Nomenclature and Properties

Practice naming alkynes from simple to relatively complex structures using the IUPAC system of nomenclature.
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Acidity of Acetylene and Alkynes

Identify relative acidities, and predict the equilibrium shift based on acid strength.
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Preparation and Reduction

Examine the different ways alkynes can be prepared and how they can be reduced to alkenes or alkanes.
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Hydrohalogenation

Probe how alkynes react with acids such as HCl, HBr, and HI.
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Hydration

Delve into the Markovnikov and anti-Markovnikov reagents that add water across a triple bond.
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Halogenation and Ozonolysis

Familiarize yourself with the reactions of chlorine and bromine with a triple bond as well as the cleavage reactions resulting from the reaction of an alkyne with ozone.
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Alkylation of Terminal Alkynes

Consider problems regarding the chain extension reactions that result from the addition of an alkyl group to a terminal alkyne.
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Synthesis Strategies

Combine all of the reaction knowledge learned in multi-step syntheses to create more complex structures.
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Radical Reactions

Continue your investigations by learning about radicals, a key reactive group in organic chemistry. Investigate the mechanisms underlying radical reactions and how the intermediates are key to explaining why specific products are formed. Get a grip on these useful molecular tools for use in larger mechanisms later in the course!

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Structure and Properties

Uncover the unique structural features and properties of radicals, which result from them having an unpaired electron.
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Patterns in Radical Mechanisms

Investigate the unique reactivity patterns of radicals.
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Chlorination

Explore the reaction conditions and mechanistic aspects of the radical chlorination reactions of alkanes, which are among the very few reactions they engage in.
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Halogenation Reactions

Contrast the mechanistic aspects and possible outcomes, including thermodynamic and kinetic considerations, of the radical halogenation reactions of alkanes involving different halogens.
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Allylic Bromination

Test yourself on the necessary reaction conditions, mechanistic aspects, and possible outcomes of radical bromination reactions of alkenes at the allylic position.
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Anti-Markovnikov Addition

Learn the necessary reaction conditions and mechanistic considerations that lead to the anti-Markovnikov addition of HBr to alkenes.
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Radical Polymerization

Analyze the reaction conditions and mechanistic aspects of the radical polymerization of alkenes.
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Synthesis

Build upon your previous practice reactions with syntheses of various compounds given certain reactants. Keep in mind the different properties of compounds, reaction mechanisms that occur, and the effect of specific catalysts or conditions. Also develop your skills in retrosynthetic analysis to reverse engineer a product and determine how it can synthesized.

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Single and Multi-Step Syntheses

Investigate how the multitude of chemical transformations known to organic chemists can be utilized sequentially to yield new and complex products starting from simpler reagents.
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Reactions and Carbon Skeletons

Explore how the carbon skeleton of an organic compound can be dissected into simpler fragments, which can then be assembled using the multitude of chemical reactions known to organic chemists.
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Retrosynthetic Analysis

Discover how organic chemists can devise synthetic strategies for the preparation of large and complex structures, as well as their tactical execution, by sequentially working backwards from the complex final product toward simpler, readily available building blocks.
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Infrared Spectroscopy and Mass Spectrometry

Utilize infrared spectroscopy and mass spectrometry to help characterize the structure of compounds. Examine various spectra to identify common patterns associated with different groups and apply them to unknown compounds.

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IR Spectroscopy

Delve into the theoretical aspects and practical applications of infrared spectroscopy for the identification and characterization of organic compounds.
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Signal Characteristics

Consider the relative positions, shapes, and magnitudes of the various spectral signals that the multitude of functional groups can generate when exposed to infrared light and the factors that can modulate them.
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Analyzing IR Spectra

Apply strategies for tackling the analysis of infrared spectra and how to decipher a molecule's spectrum for various functional groups.
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Mass Spectrometry

Analyze the theoretical principles and practical aspects of mass spectrometry, as well as the structural and functional features of a mass spectrometer.
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Analyzing Peaks and Fragments

Recognize individual and collections of peaks in a mass spectrum by correlating observed mass-to-charge ratios with potential structural fragments.
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Applications of Mass Spectrometry

Determine how various mass spectrometry modalities can be applied in combination with other spectroscopic techniques for the elucidation of chemical structures, from simple organic compounds to complex biomolecules.
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Nuclear Magnetic Resonance Spectroscopy

Building off of the electronic signature of the hydrogen and carbon nuclei, utilize this powerful technique to map the structure of a compound just by its fingerprint. Learn how to read and interpret NMR data to pinpoint stuctural groups, their relative locations, and the overall identity of a molecule.

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NMR Spectra and Characteristics

Learn how nuclear magnetic resonance spectroscopy works and its applications in identifying functional groups as well as molecular formula.
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Signals and Chemical Shift

Define chemical shift, and describe how and why molecular structure affects the chemical shift of identical nuclei in different environments.
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Integration and Multiplicity

Interpret hydrogen-1 NMR spectra by using peak integration and peak multiplicity to determine the number of hydrogens represented by each peak. Learn the source of peak multiplicity, and why it tells us about nearby hydrogen nuclei.
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NMR and Compounds

Look into how using hydrogen-1 and carbon-13 methods in tandem can tell us about the structure of a compound.
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Acquiring and Analyzing NMR Spectra

Determine how to acquire NMR spectra and use them for structural identification of unknown compounds.
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Conjugated Pi Systems and Pericyclic Reactions

Discover the unique properties and chemical reactivty of alkenes and alkynes when they are conjugated. Develop skills in using spectroscopy to identify conjugated pi systems and predicting the products of their reactions using mechanistic thinking.

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Classes and Conjugations

Compare conjugated to non-conjugated structures, and how resonance explains the stability created by conjugation.
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Molecular Orbital Theory

Study how molecular orbital theory constructs molecular orbitals by combining atomic orbitals, and how it is used to explain resonance in conjugated compounds.
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Electrophilic Addition

Apply your knowledge of electrophilic addition to normal alkenes to learn how conjugation affects the products of electrophilic addition to conjugated systems.
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Thermodynamic Versus Kinetic Control

Contrast the thermodynamically and kinetically favored products of a reaction, and how the reaction conditions can control which is produced.
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Pericyclic, Electrocyclic, and Diels-Alder Reactions

Define what pericyclic reactions are and how they can be explained by molecular orbital theory. Learn how changing the reaction conditions can change the stereochemistry of ring-opening and ring-closing reactions of conjugated molecules.
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Cycloadditions and Sigmatropic Rearrangements

Determine how molecular orbital theory can explain cycloaddition reactions other than the Diels-Alder reaction, and how it can explain rearrangement reactions of cations and of neutral molecules.
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UV-VIS Spectroscopy

Study how molecular orbital theory can explain trends in UV-visible light absorption by conjugated molecules.
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Color and Vision

Inquire into how conjugation affects the color of substances and how organic photochemical reactions are used in your eyes to receive and interpret color.
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Aromatic Compounds

Circle around and let us discover the last major compound classification in organic chemistry I, which is really just a variation of a cyclic alkene. Learn the rules on how to sniff out this class of important compound and the electronic underpinnings for their unique properties. Develop skills in naming bezene derivatives and learning reactions specific for aromatic compounds.

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Nomenclature, Structure, and Stability of Benzene

Review how to create appropriate IUPAC names for simple aromatic compounds, and understand the concept of aromaticity.
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Other Aromatic Compounds

Understand the concept of aromaticity for larger molecules, and learn about methods for the separation of some aromatic compounds.
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Reactions at the Benzylic Position

Inspect the fundamental reactions that take place on the carbon adjacent to a benzene ring, and explain why this carbon is particularly susceptible for reactions.
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Reduction of Aromatic Moiety

Consider the conditions required to completely reduce a benzene ring. Apply this strategically to produce specific products.
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Spectroscopy of Aromatic Compounds

Apply interpretation of IR and NMR spectra to analyzing aromatic compounds.
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Aromatic Substitution Reactions

Building on aromatic compounds and their unique electronic arrangment, learn how they can be used to synthesize unique compounds with various functional groups or serve as a reaction intermediate for a greater purpose! Master the mechanisms before you jump into organic chemistry II, if you dare.

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Halogenation, Sulfonation, and Nitration

Consider the mechanism and reaction conditions via which heteroatoms can be introduced into an aromatic ring via an electrophilic, aromatic substitution process.
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Friedel-Crafts Alkylation and Acylation

Investigate the mechanism and reaction conditions via which carbon side chains can be introduced into an aromatic ring via an electrophilic aromatic substitution process.
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Activating and Deactivating Groups

Analyze the structural and electronic features of substituents on an aromatic ring that can either increase or decrease the reactivity of the ring toward further reaction via electrophilic substitution.
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Substituents

Probe the structural and electronic features of substituents on an aromatic ring that determine the positions toward which additional substituents are directed during an electrophilic substitution reaction.
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Synthesis Strategies

Strategically choose the sequence of electrophilic aromatic substitution reactions, plus any other additional transformations that may be necessary, in order to yield a poly-substituted aromatic ring with all substituents in the desired relative positions.
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Substitution and Elimination-Addition

Delve into various reaction mechanisms of aromatic rings other than electrophilic substitution that serve to add and/or remove substituents from the ring.
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