The Chemical Educator
ISSN: 1430-4171 (electronic version)
Abstract Volume 15
(2010) pp 331-333
Using Curved Arrows for Retrosynthetic Analysis
John W. Keller
Department of Chemistry and Biochemistry, University
of Alaska Fairbanks, Fairbanks, AK 99775-6160, email@example.com
Published: 17 September 2010
Abstract. The purpose of this article is to advocate the wider use of curved arrows by organic chemistry students as a tool for retrosynthetic analysis, particularly for synthesis problems involving Grignard-carbonyl additions, aldol-, Claisen-, and Michael condensations, Diels-Alder, and other C‑C bond-forming reactions. This type of problem is challenging because it requires inductive reasoning that is rarely found elsewhere in the curriculum. However, solving retrosynthetic problems becomes easier when one uses several curved arrows to follow deductively the reverse mechanism. The important first steps of several example retro-reactions are described, and the curved arrow versions of these reactions are given in the Supporting Material. The main benefit of this approach is that, once the appropriate type of synthesis reaction is identified, the correct synthons structures can be generated.
Key Words: Laboratories and Demonstrations; organic chemistry; synthesis; undergraduate; problem solving; nucleophilic substitution; mechanism; retrosynthetic; enolate
(*) Corresponding author. (E-mail: firstname.lastname@example.org)
Supporting Materials:Table S1 contains the detailed reverse mechanisms of ten synthesis reactions and brief step-by-step procedures for writing the starting compound structures. Table S2 contains example single and multi-step problems with solutions based on curved arrow retrosynthetic analysis. (22 KB).