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nucleophilicity

Nucleophilicity of Amines

Bonus Topic – Nucleophilicity Of Amines The relative nucleophilicity of amines doesn’t get a lot of coverage (translation: doesn’t get tested) in many organic chemistry

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

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

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

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

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

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

Nucleophiles and Electrophiles

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

Nucleophilicity vs. Basicity

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

What Makes A Good Nucleophile?

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

Acid Base Reactions Are Fast

Here is a very common dilemma in organic chemistry as you move through the latter parts of Org 1 and then into Org 2: When more

Carbonyl Chemistry: 10 Key Concepts (Part 1)

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 on carbonyl first. Steric bulk slows down reactions.

Carbonyls: 10 key concepts (Part 2)

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 beta unsaturated carbonyls is proportional to the stability of its enolate, enolates are nucleophiles.