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by James
Lets talk about carbocations today. This is going to be really important going forward.
Carbocations are unhappy species. Why? Because theyre electron-poor: they have less than a full octet of
electrons.
So how do we cheer a poor carbocation up?
Two ways:
Donate electrons to it
Spread the positive charge out
Donate electrons
If youre poor, it helps to have rich neighbors.
So carbocations are stabilized by adjacent groups that can donate electron density. The most common example
you learn in Org 1 is alkyl groups. Alkyl groups are electron donating, since they have C-H bonds that can

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end up donating electrons to the adjacent carbocation.


For this reason, carbocation stability increases as we go from primary to secondary to tertiary.
[Theres a second situation that you generally dont encounter until Org 2, but carbocations are also stabilized
by adjacent atoms that have lone pairs. Even an atom like oxygen, which we normally think of as electron
withdrawing, can stabilize a carbocation since it can donate a pair of electrons to carbon, giving it a full
octet. This is called Pi-donation.]
Spreading out the charge
The second way carbocations are stabilized is through resonance. Charge is stabilized by distributing it over a
larger area (making it more diffuse).
Resonance helps to spread out the charge between multiple sites, which is going to decrease the charge
density on the carbon. The effect on stability of the carbocation is tremendous. For this reason, the allyl
carbocation is more stable than a normal secondary carbocation, even though it is technically primary.
Heres a summary:

Invert, always invert


It can also help to ask the opposite question. How do we destabilize a carbocation? Well, we can make it less
stable if we take electrons away. So adjacent electron-withdrawing groups destabilize carbocations. So does
making the charge more concentrated.

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Tomorrow: lets apply what weve learned, because were going to start talking about rearrangements.
Thanks for reading! James
P.S. Relevant posts:
3 factors that stabilize carbocations.
3 factors that destabilize carbocations
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1,4-addition of enolates to enones (The Michael Reaction)
1,4-addition of nucleophiles to enones
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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
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Addition of organocuprates (Gilman reagents) to acid chlorides to give ketones
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Additions to alkenes accompanied by 1,2-hydride shifts
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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
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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
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Formation of alkynes through double elimination of vicinal dibromides
Formation of amides from acid chlorides and amines
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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

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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 Lindlars 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

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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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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
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Find That Which Is Hidden
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How Are These Molecules Related?
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How To Tell Enantiomers From Diastereomers
Hybridization
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Hydroboration
Imines and Enamines
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Intramolecular Forces
Intro to Resonance
Ketones on Acid
Kinetic Thermodynamic
Making Alcohols Into Good Leaving Groups
Markovnikovs rule
Mechanisms Like Chords
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More On The E2
Newman Projections
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Nucleophilic Aromatic Substitution 2
Order of Operations!
Oxidation And Reduction
Oxidative Cleavage
Paped
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Protecting Groups
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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
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sn1/sn2/e1/e2 Temperature
Stereochemistry
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Strong And Weak Oxidants
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Stronger Donor Wins
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Sugars (2)
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t-butyl
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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
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Bond Rotations: The Steering Wheel Analogy
Bronsted and Lewis Acidity
Bulky Bases in Elimination Reactions
Carbocation Stability
Comparing E1 and E2 Mechanisms

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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: Zaitsevs 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

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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)

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What Makes A Good Nucleophile? (2)


What Makes A Good Nucleophile? (3)
Whats A Nucleophile?
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