Substitution: What is Substitution?

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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 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)
- Bromination of alkenes with Br2 to give dibromides
- Bromination of aromatic alkanes to give alkyl bromides
- Bromination of Aromatics to give Bromoarenes
- 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
- 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 Bromination of Alkanes
- Free Radical Chlorination of Alkanes
- Friedel Crafts alkylation of arenes
- Friedel-Crafts acylation of aromatic groups to give ketones
- 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
- Nitration of aromatic groups
- 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
- 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
- Substitution (SN1) with hydride shift
- Substitution with accompanying alkyl shift
- Sulfonylation of Arenes to give sulfonic acids
- The Gabriel synthesis of amines
- The haloform reaction: conversion of methyl ketones to carboxylic acids
- The Malonic Ester Synthesis
- 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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- 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 Line Diagram to a Fischer Projection
- 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 (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
- Factors that affect acidity – Aromaticity
- 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/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
- SN1: Applying the SN1 Reaction
- 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