Making OH Into A Good Leaving Group

Cancel reply

Leave a Comment

Name *

E-mail *

Website

About James
Blog
Confirming your email address…
Daily Organic Chemistry Tips
Dashboard
Feedback
Getting Started
Home
How To Succeed In Organic Chemistry
Live “Introduction To Spectroscopy” Session
Membership Cancelled
Mission
NEW! Reagents App
Online Organic Chemistry Tutoring
Oops! Wrong Membership Level
Org 2 Post Index
Organic 1
Organic 2
Organic Chemistry Study Advice
Post Index
Post Index 2
Post Index Draft
post index draft 2
Premium
Products
- 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 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
Resource Guide
Resources
Signup for the Reaction Guide
Study and Exam Tips
Summary Sheets
testtypg
Thanks for Joining!
Thanks! You’re signed up for the newsletter.
Thanks! You’re Signed Up For The Reaction Guide
Thoughts On O-Chem
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 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