Day 14 – Activating OH as a Leaving Group

I'm providing two documents for Day 14 of class: a reaction summary and my lecture slides. You can find additional summaries in Sorrell (see p.231-2 & 233-5 near end of chapter) and in my learning objectives. Summaries are highly useful ways of expressing the information that needs to be learned and I recommend that you write your own version. Use the 'predict-plan-explain' outline in the Day 14-15 learning objectives to guide what you do (and don't) write down. If your summary takes up more than 1-3 pages, it may be useful, but it isn't a summary.

Mitsunobu reaction alert. I didn't talk about this reaction in class because I ran out of time, but you need to know the reaction (i.e., know how to 'predict-plan-explain') for the next exam, but you don't need to know all of the subtleties of its mechanism. Just focus on the nucleophilic substitution step: is it SN1 or SN2? what is the ionization state of the Nu? what is the leaving group? There is considerable disagreement about the details of the mechanism. If you're interested, compare Sorrell's mechanism with alternative (and more plausible?) mechanisms presented in Wikipedia and at the Organic Chemistry Portal.

Exam alert. The next exam (Day 16) covers everything presented through Day 14, including the Mitsunobu reaction. The emphasis will be on Ch. 5 (acid-base), Ch. 6 (SNx reactions of alkyl halides), and only part of Ch. 7 (converting ROH into "RLg" and then RNu). The material from Day 15 will not be on the exam.

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