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Organic Chemistry, 6th Ed. Smith
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Organic Chemistry, 6th Ed. Smith
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Janice Gorzynski Smith
Organic Chemistry, 6th Ed. Smith
ISBN: ISBN-13: 978-1260119107, ISBN-10: 1260119106
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1: "Structure and Bonding"
(12)
Molecular Formula
Lewis Structures
Electronegativity & Bond Polarity
Formal Charge
Bonding Types
Resonance Structures
Carbocations and Carbanions
Molecular Orbitals
IHD
Constitutional Isomers
Hybridization
VSEPR Theory
2: "Acids and Bases"
(8)
Magic Number 5.7
Factors to Determine Acid Strength
Factors to Determine Base Strength
Predicting the Product
Curved Arrows
pH effects on pKa
Extraction of Organic Compounds
Radiolabeling
3: "Introduction to Organic Molecules and Functional Groups"
(6)
Functional Groups
General Forces
Boiling Point
Melting Point
Solubility
Intro to Synthesis and Retrosynthesis
4: "Alkanes"
(13)
Nomenclature - General Rules
Nomenclature of Alkanes
Newman Projections
Sawhorse Projections
Converting between Newman and Sawhorse
Staggered & Eclipse Conformations
Energy Calculations of Comformations
Conformational isomers
Torsional Strain
Stability Trend of Rings
Conformations of Cyclohexane
Energy Calculations of Chair Cyclohexane
Bicyclic Molecules
5: "Stereochemistry"
(11)
Nomenclature of Stereoisomers
Identifying Stereocenters
Diastereomers
Meso Compounds
Optical Activity
Properties of Stereoisomers
Seperation Techniques
Fischer & Newman Projections
Enantiomers
Stereoisomers
Haworth Formula
6: "Understanding Organic Reactions"
(8)
Bond Strength
Equilibrium Constant and Free Energy
Enthalpy and Entropy
Kinetics and the Rate Equation
Activation energy
Transition States
Interpreting Energy Diagrams
General Reactions
7: "Alkyl Halides and Nucleophilic Substitution"
(17)
Equilibrium Constant and Free Energy
Enthalpy and Entropy
Kinetics and the Rate Equation
Activation energy
Transition States
The Hammond Postulate
Interpreting Energy Diagrams
Synthesis of Alkyl Halides
Sn1 Reaction and Characteristics
Sn2 Reaction and Characteristics
Sn1 Vs Sn2 Summary Chart
Intramolecular Substitution Reactions
Rearangement Considerations for Sn1
Hydride Shift
Methy Shift
Ring Expansion
Ring Reduction
8: "Alkyl Halides and Elimination Reactions"
(18)
Synthesis of Alkenes
Sharpless Epoxidation
Electrophillic Addition
Nucelophilic Addition
Ozonolysis (Reductive/Oxidative-workup)
Properties of Alkenes
Nomenclature of Alkenes
Stereochemistry of Alkenes
E1 Reaction and Characteristics
E2 Reaction and Characteristics
E1 Vs E2 Summary Chart
Substitution vs Elimination Summary
Zaitsev vs Hoffman Elimination
Alkyne formation via elimination
Rearangement Considerations for E1
Conversion to alcohols
Hoffman Elimination
Zaitsev Elimination
9: "Alcohols, Ethers, and Related Compounds"
(21)
Retrosynthesis - Related to Alcohols
Properties of Alcohols
Nomenclature of Alcohols
Synthesis of Alcohols
Diols
Acid & Base properties of alcohols
Conversion to tosylates, mesylates, triflates
Alcohol Conversion to alkyl Halides
Electrophilic Substitution reactions with Alcohols
Pinacol Rearrangement
Inversion vs Double Inversion
Alcohol Protection
Protection as silyl ethers
Conversions to Alcohols
Conversion to Alkenes by dehydration
Nomenclature of Ethers
Synthesis of Ethers
Nomenclature of Epoxides
Synthesis of Epoxides
Epoxide opening Reactions
Thiol formation
10: "Alkenes and Addition Reactions"
(16)
Hydrohalogenation
Hydration
Halogenation
Halohydrin formation
Addition of Alcohol
Oxymercuration
Hydroboration
Dihydroxylation
Oxidative cleavage (Ozonolysis & KMnO4)
Hydrogenation
Rearrangements starting with Alkenes
Free Radical Addition of HBr
Stereochemistry and Regiochemistry of Alkene Reactions
oxidation of alkenes
Bromination of alkenes
Diol Formation
11: "Alkynes and Synthesis"
(13)
Properties of Alkynes
acetylide formation
Nomenclature of Alkynes
Synthesis of Alkynes
Reduction Reactions with Alkynes (Hydrogenation)
Hydration of Alkynes
Hydroboration of Alkynes
Oxymercuration of Alkynes
Addition of HX of Alkynes
Halogenation of Alkynes
Oxidative cleavage of Alkynes
Conversion to Alkenes
Retrosynthesis - Related to Alkenes and Alkynes
12: "Oxidation and Reduction"
(8)
Oxidation of Alcohols
Oxidative cleavage of vicinal diols
Epoxidation [RCOH]
Ether Cleavage with Acid
Ether Cleavage through Sn1
Thiol oxidation to disulfides
Sharpless Epoxidation of alkenes
Reduction of thioacetals to alkanes
"Spectroscopy A,B,C - Mass Spectrometry, IR and NMR Spectroscopy"
(10)
The Electromagnetic Spectrum
IR Spectroscopy
Characteristic Absorptions in IR region
NMR Theory
Magnetic Shielding
Chemical Shifts
The Number of Signals
Areas of the Peak
Spin-Spin Coupling
Chart Interpretation Trends
13: "Radical Reactions"
(8)
Conversion to alkanes
Bond Dissociation Energy
Free radical halogenation
Free Radcial Reactions
Reactivity-Selectivity Principle
Determining the Stereochemsitry of Radical Halogenation
Allylic bromination [NBS]
Miscellaneous Radical Reactions
14: "Conjugation, Resonance, and Dienes"
(14)
Principles
1,2 and 1,4 addition
Thermodynamic/Kinetic Product
Properties of dienes
Nomenclature of dienes
Synthesis of dienes
Conjugate Addition
Conjugate substitution
Diels Alder reaction
Polymerization of dienes
Diels Alder
UV Theory
Absorption Trends
UV Analysis in Medicine
15: "Benzene and Aromatic Compounds"
(5)
Nomenclature of Aromatic Compounds
Properties of Aromatic Systems
Aromaticity
Antiaromatic and Nonaromatic
Heterocyclic Compounds
16: "Reactions of Aromatic Compounds"
(16)
Nitration
Halogenation
Sulfonylation [SO/HSO]
Friedel Crafts alkylation
Friedel Crafts acylation
Iodination
Reduction of nitro groups
Reduction of benzyl carbonyl
Side chain halogenation
Side chain oxidation
electrophillic Substitution
Sulphonation
Nucleophillic Substitution
Alkylation
Benzene reactions
NBS Halogenation
17: "Introduction to Carbonyl Chemistry: Organometallic Reagents; Oxidation and Reduction"
(15)
Grignard formation
Reaction of Grignards with acid [H+]
Addition of Grignards to carbonyl compounds
Reaction of Grignards with CO2
Formation of organolithium reagents
Formation of Gilman reagents
Substitution with Gilman Reagents
Addition with Gilman reagents
Electron Counting with Metals
General Ligand Reaction Types
Stille Reaction
Sonogashira Reaction
Addition of organolithium reagents
Addition of Organolithium reagents to carbonyl compounds
General Reactions of Organometallics
18: "Aldehydes and Ketones—Nucleophilic Addition"
(31)
General Characteristics of Aldehydes and Ketones
Nomenclature of Aldehydes and Ketones
Synthesis of Aldehydes and Ketones
Hydrate formation (Gem-diols)
Nitrile Addition
Cyanohydrin formation
Reduction of aldehydes & Ketones
Grignard addition to aldehydes & ketones
Acetal & Hemiacetals
Acetal hydrolysis
Imine
Enamine
Imine reactions
Stork Enamine Reaction
Wolff-Kishner - reduction to alkanes
Clemmensen reduction to alkanes
Oxidation to carboxylic acid
Tollens Test
Reductive Amination
Wittig reaction: alkene formation
Thioacetal formation
Cannizarro Reaction
Beckmann Rearrangement
Baeyer-Villiger Reaction
Hydrolysis of Hemiacetals
Reductive Deoxygenation
Oxidation of Aldehydes and Ketones
General Reactions of aldehyde and ketones
General Reactions of Acetals and Hemiacetals
Acetal group Protecting reactions
Pinacol Rearrangement
19: "Carboxylic Acids and Nitriles"
(14)
Properties of Carboxylic Acids
Nomenclature of Carboxylic Acids
Synthesis of Carboxylic Acids
Acid/Base Principles of COOH
Conversion to Acyl halide
Conversion to Acid Anhydride
Conversion to Ester
Conversion to Amide
Conversion to Nitrile
Reduction of Carboxylic Acids
Fischer esterification reaction
Conversion to Lactones
General reactions and characterisitics of benzoyl compounds
General reactions of Carboxylic acids
20: "Carboxylic Acids and Their Derivatives- Nucleophilic Acyl Substitution"
(48)
General reactions of Carboxylic acid derivates
Nomenclature of Acyl Halides
Synthesis of of Acyl Halides
Acyl Halides Conversion to anhydrides
Acyl Halides Conversion to esters
Acyl Halides Conversion to carboxylic acids
Acyl Halides Conversion to amides
Acyl Halides Conversion to ketones
Acyl Halides Conversion to aldehydes
Curtius Rearrangement
Nucelophilic Acyl Substitution
Nomenclature of Amides
Amide Formation Using DCC
Amide Formation from Acid Halides
Amide Formation from Acid Anhydrate
Amide Formation from Nitriles
Dehydration of amides to nitriles
Hydrolysis of Amides
Amide Reduction (making Amines)
Hofmann Rearrangement
General Characterisitcs of amides
General reactions of amides
Nomenclature of Anhydrides
Synthesis of Anhydrides
Anhydrides Conversion to esters
Anhydrides Conversion to carboxylic acids
Anhydrides Conversion to amides
Cyclic Anhydrides
Hydrolysis of anhydride
Nomenclature of Esters
Synthesis of Esters
Reduction of Esters
Carbon Nucleophiles to Esters
Hydrolysis - Conversion Esters to Carboxylic Acid
Esters Conversion to Amide
Transesterification
Esters Addition of Grignard reagents
Lactones
Reduction of Lactones
Ring Opening reactions of Lactones
conversion to lactones
Synthesis of Nitriles
Substitution Reactions with Nitriles
Reduction to amines [LiAlH]
Hydrolysis to carboxylic acids
Conversion to Aldehydes and Ketones
Reduction to imines
Beckmann Rearrangement
21: "Substitution Reactions of Carbonyl Compounds at the α-Carbon"
(16)
Enolate formation
enolate ions
Keto-Enol tautomerism
Alkylation of enolates
Hell-Vollhard-Zolinsky Reaction
Decarboxylation
Alpha Alkylation Reactions
Alpha Reactions
Malonic Ester Synthesis
Acetoacetic Ester Synthesis
synthesis of Keto esters
Darzens Reaction
Alpha Reactions with Amides
Alpha Halogenation
Alpha Reactions
Haloform reaction
22: "Carbonyl Condensation Reactions"
(8)
Aldol addition reaction
Retro-aldol reaction
Claisen condensation
Dieckmann Condensation
Conjugate Addition
Conjugate addition
Robinson annulation
Michael Addition
23: "Amines"
(20)
Properties of Amines
Nomenclature of Amines
Synthesis - Azide Reduction
Synthesis - Gabriel Synthesis
Synthesis - Reductive Amination
Amines as Bases
Alkyation of Amines
Acylation of Amines
Hofmann Elimination
Cope Elimination
Hinsberg Test
Formation of Diazonium Salts
Diazonium Salts
Azo Coupling
Stork Enamine Reaction
Mannich Reaction
Enanmine Hydrolysis
Conversion to Amines
Curtius Rearrangement
Hoffman Rearrangement
24: "Carbon-Carbon Bond-Forming Reactions in Organic Synthesis"
(6)
Heck Reaction
Suzuki Reaction
Simmons–Smith reaction
Carbene Reaction
Olefin metathesis
Metathesis
25: "Pericyclic Reactions"
26: "Carbohydrates"
(15)
General Introduction
Classification of Carbohydrates
Formation of Cyclic Hemiacetal
Mutarotation
Reduction of Monosaccharides
Oxidation of Monosaccharides
Enediol Rearangement of Monosaccharides
Reducing vs Non Reducing Sugars
Osazone Formation
Glycosides
Ether and Ester Formation
Periodic Acid Reaction
Ruff Degradation
Kiliani Fischer Synthesis
Disaccharides and Polysaccharides
27: "Amino Acids and Protein"
(5)
Amino Acids
Zwitter ions
Peptide Synthesis
General Properties of Protiens
Strecker Synthesis
28: "Synthetic Polymers"
29: "Lipids"
(7)
Steroids
Metathesis
Terpenes Reactions
Terpene synthesis
Synthesis of Fatty Acids
Biosynthesis of Cholesterol
Biosynthesis of Terpenes
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