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- Organic Chemistry Reagent Guide
Reaction Guide
- 1,4-addition of enolates to enones (“The Michael Reaction”)
- 1,4-addition of nucleophiles to enones
- 1,4-addition of organocuprates (Gilman reagents) to enones
- Acidic cleavage of ethers (SN2)
- Addition Of Alcohols To Alkenes With Acid
- Addition of aqueous acid to alkenes to give alcohols
- Addition of Dichlorocarbene to alkenes to give dichlorocyclopropanes
- Addition of dichloromethylene carbene to alkenes
- Addition of Grignard reagents to aldehydes to give secondary alcohols
- Addition of Grignard reagents to esters to give tertiary alcohols
- Addition of Grignard reagents to formaldehyde to give primary alcohols
- Addition of Grignard reagents to ketones to give tertiary alcohols
- Addition of Grignard reagents to nitriles to give ketones (after hydrolysis)
- Addition of HBr once to alkynes to give alkenyl bromides
- Addition of HBr to Alkenes
- Addition of HBr twice to alkynes to give geminal dibromides
- Addition of HCl once to alkynes to give alkenyl chlorides
- Addition of HCl to Alkenes to Give Alkyl Chlorides
- Addition of HCl to alkynes twice to give geminal dichlorides
- Addition of HI once to alkynes to give alkenyl iodides
- Addition of HI twice to alkynes to give geminal diiodides
- Addition of Hydroiodic Acid to Alkenes to Give Alkyl Iodides
- Addition of LiAlH4 to aldehydes to give primary alcohols
- Addition of LiAlH4 to ketones to give secondary alcohols
- Addition of NaBH4 to aldehydes to give primary alcohols
- Addition of NaBH4 to ketones to give secondary alcohols
- Addition of organocuprates (Gilman reagents) to acid chlorides to give ketones
- Addition to alkenes accompanied by 1,2-alkyl shift
- Additions to alkenes accompanied by 1,2-hydride shifts
- Aldol addition reaction of aldehydes and ketones
- Aldol Condensation
- Alkylation of enamines with alkyl halides
- Alkylation of enolates
- Allylic bromination of alkanes using NBS
- Baeyer-Villiger Reaction
- Base-promoted formation of enolates from ketones
- Basic hydrolysis of esters (saponification)
- Beckmann Rearrangement
- Bromination of alkenes with Br2 to give dibromides
- Bromination of aromatic alkanes to give alkyl bromides
- Bromination of Aromatics to give Bromoarenes
- Cannizarro Reaction
- Chlorination of alkenes with Cl2 to give vicinal dichlorides
- Chlorination of Arenes to give Chloroarenes
- Claisen Condensation of esters
- Cleavage of ethers using acid (SN1 reaction)
- Clemmensen Reduction of Ketones/Aldehydes to Alkanes
- Conversion of acid chlorides to aldehydes using LiAlH(O-tBu)3
- Conversion of acid chlorides to esters through addition of an alcohol
- Conversion of alcohols to alkyl bromides using PBr3
- Conversion of alcohols to alkyl chlorides using SOCl2
- Conversion of alcohols to alkyl halides using HCl
- Conversion of Alkyl halides to ethers (SN1)
- Conversion of carboxylic acids into acid chlorides with SOCl2
- Conversion of carboxylic acids to carboxylates using base
- Conversion of carboxylic acids to esters using acid and alcohols (Fischer Esterification)
- Conversion of tertiary alcohols to alkyl bromides using HBr
- Conversion of tertiary alcohols to alkyl iodides with HI
- Conversion of thioacetals to alkanes using Raney Nickel
- Curtius Rearrangement of Acyl Azides to Isocyanates
- Decarboxylation of beta-keto carboxylic acids
- Dehydration of amides to give nitriles
- Deprotonation of alcohols to give alkoxides
- Deprotonation of alkynes with base to give acetylide ions
- Diels Alder Reaction of dienes and dienophiles
- Dihydroxylation of Alkenes to give 1,2-diols (vicinal diols)
- Dihydroxylation of alkenes with cold, dilute KMnO4 to give vicinal diols
- Elimination (E1) of alkyl halides to form alkenes
- Elimination (E1) with 1,2-alkyl shift
- Elimination (E1) with hydride shift
- Elimination (E2) of alkyl halides to give alkenes
- Elimination of alcohols to give alkenes using POCl3
- Elimination of water from alcohols to form alkenes using acid
- Enamine Hydrolysis
- Formation of Acetals from Aldehydes and Ketones
- Formation of alkynes through double elimination of vicinal dibromides
- Formation of amides from acid chlorides and amines
- Formation of Amides Using DCC
- Formation of anhydrides from acid halides and carboxylates
- Formation of Bromohydrins from alkenes using water and Br2
- Formation of bromohydrins from alkenes using water and NBS
- Formation of Carboxylic Acids from Acyl Chlorides
- Formation of carboxylic acids from Grignard reagents and CO2
- Formation of chlorohydrins from alkenes using water and Cl2
- Formation of Cyanohydrins from ketones and aldehydes
- Formation of cyclopropanes from alkenes using methylene carbene (:CH2)
- Formation of Diazonium Salts from Aromatic Amines
- Formation of enamines from ketones/aldehydes and secondary amines
- Formation of epoxides from alkenes using m-CPBA
- Formation of epoxides from bromohydrins
- Formation of Gilman reagents (organocuprates) from alkyl halides
- Formation of Grignard Reagents from Alkenyl Halides
- Formation of Grignard Reagents from Alkyl Halides
- Formation of hydrates from aldehydes/ketones and H2O
- Formation of imines from primary amines and ketones
- Formation of organolithium reagents from alkyl halides
- Formation of thioacetals from aldehydes and ketones
- Formation of tosylates from alcohols
- Free Radical Addition of HBr To Alkenes
- Free Radical Bromination of Alkanes
- Free Radical Chlorination of Alkanes
- Friedel Crafts alkylation of arenes
- Friedel-Crafts acylation of aromatic groups to give ketones
- Halogenation of Alkynes
- Hell-Vollhard-Zelinsky Reaction
- Hofmann elimination of alkylammonium salts to give alkenes
- Hofmann Rearrangement of Amides to Amines
- Hydroboration of Alkenes
- Hydroboration of alkynes using BH3 to give aldehydes
- Hydrogenation of Alkenes to give Alkanes
- Hydrogenation of Alkynes to Alkanes using Pd/C
- Hydrolysis of acetals to give aldehydes and ketones
- Hydrolysis of esters to carboxylic acids with aqueous acid
- Hydrolysis of imines to give ketones (or aldehydes)
- Hydrolysis of nitriles with aqueous acid to give carboxylic acids
- Iodination of alkenes to give vicinal diiodides (1,2-diiodides)
- Iodination of Aromatics with I2
- Keto-enol tautomerism
- Kiliani-Fischer Synthesis
- Nitration of aromatic groups
- Nucleophilic Aromatic Substitution (SNAr)
- Nucleophilic Aromatic Substitution Via Arynes
- Opening of epoxides with acid and water to give trans diols
- Opening of epoxides with nucleophiles under acidic conditions
- Oxidation of aldehydes to carboxylic acids using Cr(VI)
- Oxidation of aldehydes to carboxylic acids with Ag2O
- Oxidation of aromatic alkanes with KMnO4 to give carboxylic acids
- Oxidation of primary alcohols to aldehydes
- Oxidation of Primary Alcohols to Aldehydes using PCC
- Oxidation of primary alcohols to carboxylic acids
- Oxidation of secondary alcohols to ketones using PCC
- Oxidation of thiols to disulfides
- Oxidative cleavage of 1,2-diols to give aldehydes/ketones
- Oxidative cleavage of alkenes to give ketones/carboxylic acids using ozone (O3) – (“oxidative workup”)
- Oxidative cleavage of alkenes to ketones/carboxylic acids using KMnO4
- Oxidative Cleavage of Alkynes with KMnO4
- Oxidative Cleavage of Alkynes with Ozone (O3)
- Oxymercuration of Alkenes to form Ethers using Hg(OAc)2
- Oxymercuration of Alkynes
- Oxymercuration: Alcohols from alkenes using Hg(OAc)2 and Water
- Ozonolysis of alkenes to ketones and aldehydes (reductive workup)
- Partial reduction of alkynes to trans alkenes using sodium and ammonia
- Partial reduction of alkynes with Lindlar’s catalyst to give cis alkenes
- Pinacol Rearrangement
- Polymerization of dienes with acid
- Protection of alcohols as silyl ethers
- Protonation of alcohols to give oxonium ions
- Protonation of Grignard reagents to give alkanes
- Reaction of alkyl halides with water to form alcohols (SN1)
- Reaction of epoxides with nucleophiles under basic conditions
- Reactions of Diazonium Salts
- Reduction of aromatic ketones to alkanes with Pd/C and hydrogen
- Reduction of aromatic nitro groups to amino groups
- Reduction of carboxylic acids to primary alcohols using LiAlH4
- Reduction of esters to aldehydes using DIBAL
- Reduction of esters to primary alcohols using LiAlH4
- Reduction of nitriles to primary amines with LiAlH4
- Reductive Amination
- Sharpless Epoxidation
- SN2 of Cyanide with Alkyl Halides to give Nitriles
- SN2 reaction between azide ion and alkyl halides to give alkyl azides
- SN2 Reaction of Acetylide Ions with Alkyl Halides
- SN2 reaction of alkoxide ions with alkyl halides to give ethers (Williamson synthesis)
- SN2 reaction of alkyl halides with hydroxide ions to give alcohols
- SN2 reaction of amines with alkyl chlorides to give ammonium salts
- SN2 reaction of carboxylate ions with alkyl halides to give esters
- SN2 reaction of hydrosulfide ion with alkyl halides to give thiols
- SN2 reaction of organocuprates (Gilman reagents) with alkyl halides to give alkanes
- SN2 reaction of thiolates with alkyl halides to give thioethers (sulfides)
- SN2 reaction of water with alkyl halides to give alcohols
- Stille Reaction
- Substitution (SN1) with hydride shift
- Substitution with accompanying alkyl shift
- Sulfonylation of Arenes to give sulfonic acids
- Suzuki Reaction
- The Gabriel synthesis of amines
- The haloform reaction: conversion of methyl ketones to carboxylic acids
- The Heck Reaction
- The Malonic Ester Synthesis
- The Mannich Reaction
- The Robinson Annulation
- Transesterification promoted by alkoxides
- Wittig Reaction – conversion of ketones/aldehydes to alkenes
- Wolff Kishner Reaction – conversion of ketones/aldehydes to alkanes
- Wolff Rearrangement
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The Cat Line Diagram
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  - Conjugation
- “Initial Tails” and “Final Heads”
- 3 Ways To Make OH A Better Leaving Group
- A Simple Formula For 7 Important Aldehyde/Ketone Reactions
- Acetoacetic
- Acids (Again!)
- Activating and Deactivating
- Actors In Every Acid Base Reaction
- Addition – Elimination
- Addition Pattern 1 – Carbocations
- Addition pattern 2 – 3 membered rings
- Addition Reactions
- Alcohol Personality Adjustment
- Aldehydes And Ketones – Addition
- Alkene Pattern #3 – The “Concerted” Pathway
- Alkyl Rearrangements
- Alkynes – 3 Patterns
- Alkynes: Deprotonation and SN2
- Amines
- Aromaticity: Lone Pairs
- Avoid These Resonance Mistakes
- Best Way To Form Amines
- Bulky Bases
- Carbocation Stability
- Carbocation Stability Revisited
- Carboxylic Acids are Acids
- Chair Flips
- Cis and Trans
- Conformations
- Conjugate Addition
- Curved Arrow Refresher
- Curved Arrows
- Decarboxylation
- Determining Aromaticity
- Diels Alder Reaction – 1
- Dipoles: Polar vs. Covalent Bonding
- E2 Reactions
- Electronegativity Is Greed For Electrons
- Electrophilic Aromatic Substitution
- Electrophilic Aromatic Substitution – Directing Groups
- Elimination Reactions
- Enantiocats and Diastereocats
- Enolates
- Epoxides – Basic and Acidic
- Evaluating Resonance Forms
- Figuring Out The Fischer
- Find That Which Is Hidden
- Formal Charge
- Frost Circles
- Gabriel Synthesis
- Grignards
- Hofmann Elimination
- How Acidity and Basicity Are Related
- How Are These Molecules Related?
- How Stereochemistry matters
- How To Stabilize Negative Charge
- How To Tell Enantiomers From Diastereomers
- Hybridization
- Hybridization Shortcut
- Hydroboration
- Imines and Enamines
- Importance of Stereochemistry
- Intermolecular Forces
- Intro to Resonance
- Ketones on Acid
- Kinetic Thermodynamic
- Making Alcohols Into Good Leaving Groups
- Markovnikov’s rule
- Mechanisms Like Chords
- Mish Mashamine
- More On The E2
- Newman Projections
- Nucleophiles & Electrophiles
- Nucleophilic Aromatic Substitution
- Nucleophilic Aromatic Substitution 2
- Order of Operations!
- Oxidation And Reduction
- Oxidative Cleavage
- Paped
- Pi Donation
- Pointers on Free Radical Reactions
- Protecting Groups
- Protecting Groups
- Proton Transfer
- Putting it together (1)
- Putting it together (2)
- Putting it together (3)
- Putting the Newman into ACTION
- Reaction Maps
- Rearrangements
- Recognizing Endo and Exo
- Redraw / Modify
- Return of The SN2
- Robinson Annulation
- Robinson Annulation Mech
- Second Most Important Reactions of Alkynes: Lindlar – Na/NH3
- Sigma and Pi Bonding
- SN1 vs SN2
- sn1/sn2 – Putting It Together
- sn1/sn2/e1/e2 – Exceptions
- sn1/sn2/e1/e2 – Nucleophile
- sn1/sn2/e1/e2 – Solvent
- sn1/sn2/e1/e2 – Substrate
- sn1/sn2/e1/e2 – Temperature
- Stereochemistry
- Strong Acid Strong Base
- Strong And Weak Oxidants
- Strong and Weak Reductants
- Stronger Donor Wins
- Substitution
- Sugars (2)
- Synthesis (1) – “What’s Different?”
- Synthesis (2) – What Reactions?
- Synthesis (3) – Figuring Out The Order
- Synthesis Part 1
- Synthesis Study Buddy
- Synthesis: Walkthrough of A Sample Problem
- Synthesis: Working Backwards
- t-butyl
- Tautomerism
- The Awesomeness Of The SN2
- The Claisen Condensation
- The E1 Reaction
- The Inflection Point
- The Meso Trap
- The Michael Reaction
- The Nucleophile Adds Twice (to the ester)
- The One-Sentence Summary Of Chemistry
- The Second Most Important Carbonyl Mechanism
- The Single Swap Rule
- The SN1 Reaction
- The SN2 Reaction
- The Wittig Reaction
- Three Exam Tips
- Tips On Building Molecular Orbitals
- Top 10 Skills
- Try The Acid-Base Reaction First
- Two Key Reactions of Enolates
- Welcome
- What makes a good leaving group?
- What Makes A Good Nucleophile?
- What to expect in Org 2
- Work Backwards
- Zaitsev’s Rule
Tuesday Oct 22 Acid Base Webinar at 9pm EST
Videos
- A Simple Trick For Determining R/S
- Applying E2 Reactions with Newman Projections
- Bond Rotations: Exercise 1
- Bond Rotations: Exercise 2
- Bond Rotations: Exercise 3
- Bond Rotations: Exercise 4
- Bond Rotations: Exercise 5
- Bond Rotations: The “Steering Wheel” Analogy
- Bronsted and Lewis Acidity
- Bulky Bases in Elimination Reactions
- Carbocation Stability
- Comparing E1 and E2 Mechanisms
- Comparing E1 and E2 Stereochemistry
- Comparing the E1 and SN1
- Comparing the SN1 and SN2
- Converting a Fischer Projection To A Line Diagram
- Converting a Line Diagram to a Fischer Projection
- Converting a Newman Projection to a Line Diagram
- Curved Arrows
- Determining R/S on a Fischer Projection
- E1 with Rearrangement
- E1 With Rearrangement (2)
- Elimination Exercise: Zaitsev’s Rule
- Elimination Reactions in Cyclohexanes
- Elimination Reactions in Cyclohexanes (2)
- Evaluating Resonance Forms (1) Charges
- Evaluating Resonance Forms (2) Octets
- Evaluating Resonance Forms (3) Negative Charge
- Evaluating Resonance Forms (4) Positive Charge
- Evaluating Resonance Forms (5) Aromaticity
- Exercise: Condensed Formula (1)
- Exercise: Condensed Formula (2)
- Factors that affect acidity – Aromaticity
- Factors That Affect Acidity (1) Charge Density
- Factors That Affect Acidity (2) Electronegativity
- Factors That Affect Acidity (3) Polarizability
- Factors That Affect Acidity (4) Electron Withdrawing Groups
- Factors That Affect Acidity (4) Resonance
- Factors That Affect Acidity (6) – Orbitals
- Formal Charge (1) – Atomic Charge
- Formal Charge (2) – Introduction to Formal Charge
- Formal Charge Exercise: Allyl Carbocation
- Formal Charge Exercise: CH2N2
- Formal Charge Exercise: CH3NO2
- Formal Charge Exercise: CN
- Formal Charge Exercise: CO3
- Formal Charge Exercise: Hidden Hydrogens
- Formal Charge Exercise: Hidden Lone Pairs
- Formal Charge Exercise: N3
- Formal Charge Exercise: NH4
- Formal Charge Exercise: O3
- Formal Charge Exercise: Radicals and Carbenes
- Hidden Hydrogens
- How Formal Charge Can Mislead
- How Heat Affects Elimination Reactions
- How to draw an enantiomer
- How To Use A pKa Table
- In Summary: Resonance
- Introduction to Elimination
- Introduction to pKa
- Introduction to Rearrangements
- Introduction to Resonance
- Introduction to the E2 Reaction
- Introduction to the SN1: Experiments
- Introduction to the SN2: Experiments
- Key Patterns in Formal Charge
- Line Drawings
- Making OH Into A Good Leaving Group
- Rearrangement Reactions: Alkyl Shifts
- Rearrangement: Hydride Shift
- Rearrangements: Carbocation Stability
- Resonance – Common Mistakes (1)
- Resonance – Common mistakes (2)
- SN1 Exercise: The Substrate
- SN1 Reaction Energy Diagram
- SN1 vs. SN2 Overview
- SN1 With Alkyl Shift (1)
- SN1 With Alkyl Shift (2)
- SN1 With Hydride Shift
- SN1: Applying the SN1 Reaction
- SN1/SN2/E1/E2 – Substrate
- SN1/SN2/E1/E2 Decision – Overview
- SN1/SN2/E1/E2 Decision – Solvent
- SN1/SN2/E1/E2 Decision – Temperature
- SN1/SN2/E1/E2 Decision – The Nucleophile/Base
- SN2 Exercise: Apply the SN2
- SN2 Exercise: Leaving Groups
- SN2 Exercise: The Substrate
- Solvents in SN1 and SN2 Reactions
- Stereochemistry Exercise 1
- Stereochemistry Exercise 2
- Stereochemistry Exercise 3
- Stereochemistry Exercise 4
- Stereochemistry Exercise 5
- Strong and Weak Acids
- Substitution: What is Substitution?
- The 4 Components of Every Acid Base Reaction
- The E1 Reaction
- The Golden Rule of Acid Base Reactions
- The Single Swap Rule
- The SN1 Mechanism
- The SN2 Mechanism
- The SN2 Reaction Energy Diagram
- Understanding R/S Relationships
- Unequal Resonance Forms
- Using Electronegativity to Find Reactive Sites on a Molecule
- What Makes A Good Leaving Group?
- What Makes A Good Nucleophile? (1)
- What Makes A Good Nucleophile? (2)
- What Makes A Good Nucleophile? (3)
- What’s A Nucleophile?
- Zaitsev’s Rule
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