Comparing Carbonyl Chemistry in Comprehensive Introductory Organic Chemistry Textbooks

Learning the chemistry of compounds containing carbonyl groups is difficult for undergraduate students because of a convolution of multiple possible reaction partly sites, competitive reactions taking place at those sites, different criteria needed to discern between the mechanisms of these reactions, and no straightforward selection method applicable to all. Factual inaccuracies in some recently used comprehensive introductory organic chemistry textbooks can distract and confuse students. Student interest, combined with some inconsistencies, prompted a systematic comparison of these textbooks, enabling some suggestions for improvement, Students also selected a preferred order of presentation in which carbonyl chemistry should appear for optimal learning: carboxylic acids, aldehydes, ketones, carboxylic acid derivatives, alpha,beta-unsaturated carbonyls, and carbonyl compounds that undergo enol chemistry. This ordering is generally based on a combination of (1) grouping according to the purpose of the functional group, (2) increasing complexity of reactions with a nucleophile, and (3) decreasing carbonyl compound reactivity. In order to facilitate solving carbonyl chemistry problems and understanding these competing factors, information about the reactions is presented in three forms: a text discussion, a Summary Sheet, and a Decision Tree. The recommendations are consistent, descriptive, and pedagogically useful, and they should remedy many discrepancies.