nucleophilicity

Guest Post On SN1/SN2/E1/E2 (3): Step 1 – The Nucleophile

Guest Post On SN1/SN2/E1/E2 (3): Step 1 – The Nucleophile

November 12, 2013

Following from Adam’s last guest post on the SN1/SN2/E1/E2 (“The Leaving Group“) here is part 3 of the series!  – James Step One: What is the nature of the nucleophile? by @azmanam Last time, …

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Guest Post on SN1/SN2/E1/E2 (1): Why Electrons Are Like A Hyperactive Child

Guest Post on SN1/SN2/E1/E2 (1): Why Electrons Are Like A Hyperactive Child

November 4, 2013

Note (from James) When my friend Adam  from The Chemistry Blog offered to write a series of posts on Substitution and Elimination, I immediately said “yes”. This is one of the topics that many students st…

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Deciding SN1/SN2/E1/E2 (3) – The Solvent

Deciding SN1/SN2/E1/E2 (3) – The Solvent

December 4, 2012

The Quick N’ Dirty Guide To SN1/SN2/E1/E2 Reactions, Part 3 Let’s continue with our Quick N Dirty guide to SN1/SN2/E1/E2 – a quick walkthrough of thinking through this reaction decision. After having…

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What Makes A Good Nucleophile?

What Makes A Good Nucleophile?

June 18, 2012

If you read the last post, you’ll recall that a nucleophile is a species that donates a pair of electrons to form a new covalent bond. Nucleophilicity is measured by comparing reaction rates; the faster the reac…

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Nucleophilicity vs. Basicity

Nucleophilicity vs. Basicity

June 6, 2012

Following up on Nucleophiles and Electrophiles, here’s a common question students have about nucleophilicity: What’s the difference between nucleophicity and basicity? Great, great question. First of all, …

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Nucleophiles and Electrophiles

Nucleophiles and Electrophiles

June 5, 2012

All through the series on understanding where electrons are, and how they flow, we’ve been talking about how the basis of chemistry is that opposite charges attract and like charges repel, and that in reactions,…

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Acid Base Reactions Are Fast

Acid Base Reactions Are Fast

May 21, 2012

Common dilemma in organic chemistry as you move through the latter parts of Org 1 and then into Org 2: When more than one reaction is possible, how do you know which one will happen? In a steel cage match between an a…

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Breaking Down Carbonyl Reaction Mechanisms: Anionic Nucleophiles (Part 1)

Breaking Down Carbonyl Reaction Mechanisms: Anionic Nucleophiles (Part 1)

April 26, 2010

I’m going to spend today going into the mechanisms of some of the reactions in the summary sheet I posted last time. Like I said in that post, I think that about 98% of the mechanisms of the 110 combinations on …

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Carbonyls: 10 key concepts (Part 2)

Carbonyls: 10 key concepts (Part 2)

April 6, 2010

5 more key concepts: Carbonyls make adjacent alkyl groups more acidic, the more electrophilic the carbonyl, the more acidic its alpha protons, carbonyls activate alkenes toward nucleophilic attack, reactivity of alpha…

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Carbonyl Chemistry: 10 Key Concepts (Part 1)

Carbonyl Chemistry: 10 Key Concepts (Part 1)

April 4, 2010

The weaker the base, the better the leaving group. Electron withdrawing groups make the carbonyl more electrophilic. Electron donors make the carbonyl *less* electrophilic. Carboxylic acid derivatives always protonate…

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