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Organic Chemistry Reaction Mechanisms Guide

This document discusses various organic chemistry reaction mechanisms including: - Nucleophilic substitution reactions (SN) where a nucleophile attacks and bonds to a positive center. This includes bimolecular (SN2) and unimolecular (SN1) reactions. - Elimination reactions (E) where groups are eliminated from a reactant to form a double bond. This includes bimolecular (E2) and unimolecular (E1) reactions. - Electrophilic addition reactions (AE) where carbon-carbon double or triple bonds are attacked by an electrophile. - Nucleophilic addition reactions (AN) where nucleophiles add to the carbonyl group.

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Tran Hieu Quoc
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7 views21 pages

Organic Chemistry Reaction Mechanisms Guide

This document discusses various organic chemistry reaction mechanisms including: - Nucleophilic substitution reactions (SN) where a nucleophile attacks and bonds to a positive center. This includes bimolecular (SN2) and unimolecular (SN1) reactions. - Elimination reactions (E) where groups are eliminated from a reactant to form a double bond. This includes bimolecular (E2) and unimolecular (E1) reactions. - Electrophilic addition reactions (AE) where carbon-carbon double or triple bonds are attacked by an electrophile. - Nucleophilic addition reactions (AN) where nucleophiles add to the carbonyl group.

Uploaded by

Tran Hieu Quoc
Copyright
© Attribution Non-Commercial (BY-NC)
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd

ORGANIC CHEMISTRY

Dr Nam T. S. Phan Faculty of Chemical Engineering HCMC University of Technology Office: room 211, B2 Building Phone: 38647256 ext. 5681 Email: ptsnam@[Link]
1

Chapter 3:

INTRODUCTION TO REACTION MECHANISMS

Reaction mechanism: the description of the step-by-step process by which reactants are changed / converted into products

Nucleophilic substitution Electrophilic substitution Elimination

Nucleophilic addition Electrophilic addition

NUCLEOPHILIC SUBSTITUTION REACTIONS (SN)


A nucleophile: an electron-rich species that can form a covalent bond by donating 2 electrons to a positive center A nucleophile is any negative / neutral molecule that has 1 unshared electron pair Substitution reaction: chemical reaction in which 1 atom / group replaces another atom / group in the structure of a molecule In a nucleophilic substitution reaction, a nucleophile attacks / bonds with the positive center
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BIMOLECULAR NUCLEOPHILIC SUBSTITUTION REACTION (SN2)

UNIMOLECULAR NUCLEOPHILIC SUBSTITUTION REACTION (SN1)

Note: slow step is rate-determining step

ELIMINATION REACTIONS

In an elimination reaction: + Groups / atoms are eliminated from a reactant + A double bond is formed between the 2 carbons from which atoms are eliminated
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BIMOLECULAR ELMINATION (E2)

Strong base

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UNIMOLECULAR ELMINATION (E1)

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Weak base

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ELETROPHILIC ADDITION REACTIONS (AE)


Electrophilic: electron-seeking / loving Most electrophiles: + Are positively charged + Have an atom which carries a partial positive charge + Have an atom which does not have an octet of electrons An electrophilic addition reaction is an addition reaction where carbon-carbon double bonds or triple bonds are attacked by an electrophile 13

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Not a carbocation, but a cyclic halonium ion More stable than carbocation

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NUCLEOPHILIC ADDITION REACTIONS (AN)


The carbonyl group is polar because the oxygen, being more electronegative, has greater share of double-bond electrons The partial positive carbon can be attacked by nucleophiles

The addition of nucleophiles to the carbon atom of the carbonyl group in nucleophilic addition reactions 16

Reaction mechanism
Positive center A nucleophile
Rate-determining step

slow

fast

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Examples:

Nucleophiles

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ELECTROPHILIC SUBSTITUTION REACTIONS (SE)


In an electrophilic substitution reaction, an electrophile substitutes for a hydrogen of an aromatic compound

Although benzene has 3 double bonds, the overall reaction is electrophilic substitution rather than electrophilic addition 19

Reaction mechanism
Rate-determining step

An electrophile

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Examples:

An electrophile

Rate-determining step

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