How SN2 Reactions Look Like (Animation) | Organic Chemistry Substitution Mechanism
๐ Letโs take a โmore visual lookโ (is that a pleonasm?) at SN2 reactions, geometries and molecular structures.
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00:00 Classic SN2 reaction (Williamson ether synthesis)
02:14 Sterics in SN2 reactions
02:44 Intramolecular SN2: synthesis of aldingenin C
Source: J. Org. Chem. 2014, 79, 9373 | Synthesis and Structural Revision of a Brominated Sesquiterpenoid, Aldingenin C
The bimolecular nucleophilic substitution (SN2 reaction) is essential to the understanding of organic chemistry fundamentals. In the SN2 reaction, a nucleophile forms a new bond to an sp3-hybridised carbon via a backside attack (electrophile). The leaving group (the group that gets substituted) dissociates in a concerted (simultaneous) manner. This differs from the step-wise SN1 reaction where the rate-determining step is dissociation of the leaving group, separate from the nucleophilic attack in SN1.
Some recommended books on organic synthesis:
- Clayden, Greeves, Warren; Organic Chemistry (basic organic chemistry knowledge)
- Wyatt, Warren; Organic Synthesis: The Disconnection Approach (excellent introduction to retrosynthesis)
- Kurti, Czako; Strategic Applications of Named Reactions in Organic Synthesis (extensive toolkit of functional group reactions and applications thereof with common conditions)
- Nicolaou; Classics in Total Synthesis 1-3 (the ultimate total synthesis trilogy)
- Nicolaou; Molecules That Changed the World (the worldโs most important molecules and their impact on everyday life)
- Carreira, Kvaerno; Classics in Stereoselective Synthesis (compilation of the groundbreaking methods of stereoselective synthesis and application to synthesis of stereochemically complex structures)
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How SN2 Reactions Look Like (Animation) | Organic Chemistry Substitution Mechanism