CHM 25500

Organic Chemistry

Purdue University

A study of aliphatic and aromatic hydrocarbons and their simple derivatives in terms of (a) structure# bonding# etc.; (b) general syntheses and reactions; and (c) a logical modern rationale for fundamental phenomena as supported by reactivity orders# orientation effects# stereochemistry# and relative rates. Recommended for biology majors. Typically offered Fall Spring.
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All CHM 25500 Materials | Summer 2015

CHM 25500 Final: Organic Chemistry_Final Exam Study Guide [Helped Me Get An A!]
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CHM 255 Lecture 1 Initial ReviewElectron ConfigurationsAtoms consist of a nucleus surrounded by electronsElectrons exist in shells (can also be thought of as levels)22n electrons in each shellElectrons move around the nu...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 31 - Electrophile, Nucleophilic Substitution, Nucleophile
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CHM 255 - Lecture 31 - Substitution Vs. Elimination Reactions Substitution and Elimination Reactions ● Substitution and elimination reactions often occur at the same time and compete with one ...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 33 - Alkoxide, Leaving Group, Electrophile
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CHM 255 Lecture 33 Reactions of AlcoholsAlcohols as Sources of NucleophilesAn alkoxide (deprotonated alcohol) may act as a nucleophile and can attack an alkyl halide as in the following reactionReactions like this are ca...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 32 - Thiol, Acid Dissociation Constant, Hydrogen Bond
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CHM 255 - Lecture 32 - Alcohols and Thiols Definitions ● Alcohols are compounds that contain hydroxyl groups (OH) attached to a3 sp hybridized carbon ● Thiols are compounds that co...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 29 - Nucleophilic Substitution, Sn2 Reaction, Protic Solvent
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CHM 255 - Lecture 29 - Solvents and Nucleophilicity Solvents and Nucleophilicity ● Nucleophilic substitution reactions are carried out in the midst of solvents ● The type of solvent determines t...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 28 - Nucleophilic Substitution, Leaving Group, Alpha And Beta Carbon
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CHM 255 - Lecture 28 - Properties of Sn2 Reactions Stereochemical Properties of Sn2 Reactions ● In nucleophilic substitution reactions, the nucleophile always attacks from the side opposite th...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 30 - Butene, Nucleophile, Leaving Group
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CHM 255 - Lecture 30 - Beta Elimination Reactions Beta Elimination Reactions ● Beta elimination reactions are those in which a small molecule (such as HCl, HBr, HI, or HOH) is eliminated from ad...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 27 - Allyl Group, Levomefolic Acid, Nucleophilic Substitution
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CHM 255 - Lecture 27 - Naturally Occurring Nucleophilic Substitution Reactions Synthesis of Biologically Significant Molecules ● Many biologically significant molecules are synthesized through nucleophilic ...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 23 - Nucleophile, Peroxy Acid, Stereospecificity
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CHM 255 - Lecture 23 - Oxidation/Reduction Reactions and the Stereochemistry of Electrophilic Addition Oxidation vs. Reduction ● In order to determine whether a reaction involves oxidation or reduction, loo...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 24 - Chain Propagation, Chain Termination, Halogenation
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CHM 255 - Lecture 24 - Alkyl Halides Nomenclature ● When naming alkyl halides the same rules apply as for naming alkanes, alkenes, and alkynes ● Use a prefix describing which halog...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 26 - Concerted Reaction, Rate Equation, Sn1 Reaction
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CHM 255 - Lecture 26 - Mechanism of Nucleophilic Substitution Reactions Mechanism Possibility One 1. The nucleophile attacks the electrophile 2. The leaving group leaves ● NOT POSSIBLE ...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 25 - Leaving Group, Electrophile, Nucleophile
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CHM 255 - Lecture 25 - Reactions of Alkyl Halides Classification of Alkyl Halides ● Primary alkyl halides contain a carbon attached to a halogen, two hydrogens and one R group ● Se...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 22 - Conjugated System, Allyl Group, Alkene
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CHM 255 - Lecture 22 - Electrophilic Addition to Conjugated Alkenes and Addition of 2 to Alkenes Conjugated Double Bonds ● Conjugated double bonds occur when two or more double bonds are separated ...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 17 - Bond-Dissociation Energy, Bond Length
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CHM 255 - Lecture 17 Intro to Alkenes and Alkynes Properties of Bonds in Alkanes, Alkenes, and Alkynes ● Bond length ○ Alkanes have the longest C-C bonds at 1.54 Angstroms ○...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 18 - Substituent, Potential Energy, Activation Energy
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CHM 255 - Lecture 18 - Alkenes and Alkynes: Reactions and the E-Z System Distinguishing Between Cis and Trans Isomers (E-Z) ● A different system must be used to distinguish between cis and trans isomers for ...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 21 - Electrophilic Addition, Alkyne, Electrophile
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CHM 255 - Lecture 21 - Electrophilic Addition to Alkynes Electrophilic Addition of H-X to Alkynes ● Very similar to electrophilic addition of H-X to alkenes ● Mechanism: ...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 20 - Hyperconjugation, Ion, Pi Bond
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CHM 255 - Lecture 20 - Reaction Intermediates: Carbocations Carbocations ● Carbocations are molecules that contain an 2p hybridized carbon with 3 groups attached and a positive charge ...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 19 - Electrophilic Addition, Reaction Mechanism, Pi Bond
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CHM 255 - Lecture 19 - Reaction Mechanisms Reaction Mechanisms ● A reaction mechanism is the step by step process of a reaction ● There are many possible organic reactions, but only a few reacti...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 5 - Sigma Bond, Acetylene
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CHM 255 - Lecture 5 - Hybridization of Atomic Orbitals sp 3ybrid Orbitals ● Hybrid orbitals occur when the electrons in an atom are rearranged in order to bond more effectively to another atom...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 15 - Acid Dissociation Constant
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CHM 255 - Lecture 15 - Acid-Base Reactions General Acid-Base Reaction Predicting the Net Direction of an Acid-Base Reaction ● “The net direction of an acid-base reaction depends on the relati...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 10 - Cycloalkane, Chemical Formula, Enantiomer
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CHM 255 - Lecture 10 - Cis and Trans Isomers and Stereochemistry Cis and Trans Isomers ● When there are two substituents they can be attached to a cycloalkane in one of two ways: ...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 13 - Stereocenter, Enantiomer, Boiling Point
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CHM 255 - Lecture 13 - Properties of Stereoisomers Cyclic Molecules With More Than One Stereocenter ● Cis and trans forms of molecules are actually diastereomers ● Look out for planes of symmetr...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 11 - Stereocenter, Substituent, Enantiomer
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CHM 255 - Lecture 11 - Distinguishing Between Enantiomers How Enantiomers are Differentiated ● There are two possible orientations for a stereocenter ○ R (right handed, from Latin rectus) ...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 4 - Ester, Acetamide, Carboxylic Acid
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CHM 255 - Lecture 4 - Continued Functional Groups and Molecular Shapes Functional Groups ● Amides ○ Carboxylic acid derivative ○ Contain carbonyl group bonded to NR2group ...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 3 - Methyl Acetate, Formal Charge, Organic Compound
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CHM 255 - Lecture 3 - Initial Review Continued and New Material Formal Charge ● Allows you to figure out where charges are located within a molecule ● Formal charge = (initial number of valence el...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 1 - Electron Shell, Angular Momentum Coupling, Pauli Exclusion Principle
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CHM 255 - Lecture 1 - Initial Review Electron Configurations ● Atoms consist of a nucleus surrounded by electrons ● Electrons exist in shells (can also be thought of as levels)...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 7 - Dihedral Angle, Newman Projection, Ethane
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CHM 255 - Lecture 7 - Structures of Unbranched Alkanes 3D Structure of Unbranched Alkanes ● Bonds can rotate, creating different possible structures for molecules of the same composition ...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 12 - Stereocenter, Stereoisomerism, Stereochemistry
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CHM 255 - Lecture 12 - Fischer Projections and Diastereomers Fischer Projections ● 2-D representations of chiral centers ○ Vertical lines represent bonds going into the plane ...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 8 - Structural Isomer, Isobutane, Chemical Formula
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CHM 255 - Lecture 8 - Branched Alkanes and Cycloalkanes Constitutional Isomers ● Molecules with the same molecular formula but with different arrangements of atoms are called constitutional isom...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 6 - Lewis Structure, Electronegativity, Ketone
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CHM 255 - Lecture 6 - Resonance and Intro to Alkanes Resonance ● For some molecules, there are many possible valid Lewis structures ● It is not always possible to accurately represent a molecule u...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 2 - Valence Electron, Ionic Bonding, Fluorine
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CHM 255 - Lecture 2 - Initial Review Continued Valence Electrons ● Valence electrons = electrons in the outermost shell ● Valence electrons are responsible for bond formation between atoms Ele...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 16 - Bond-Dissociation Energy, Conjugate Acid, Electronegativity
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CHM 255 - Lecture 16 - Structural Effects on Acidity and Basicity What causes the relative strength or weakness of an acid? ● The strength of an acid depends on the stability of its conjugate base: the more ...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 14 - Conjugate Acid, Acid Dissociation Constant, Equilibrium Constant
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CHM 255 - Lecture 14 - Acids and Bases Basics Definitions ● Bronsted-Lowry definition of acids and bases ○ An acid is a proton donor ○ A base is a proton acceptor ...

Chemistry
CHM 25500
Animesh V.Aditya
CHM 25500 Lecture Notes - Summer 2015, Lecture 9 - Ring Strain, Cyclohexane Conformation, Cyclopropane
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CHM 255 - Lecture 9 - Cycloalkanes Conformations of Cycloalkanes ● General formula for cycloalkanes:nC2n ● Angle strain: “the increase in potential energy of a molecule due to bond angles ...

Chemistry
CHM 25500
Animesh V.Aditya
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