Reading Guide 8-12 8-14 PDF

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exam 4...

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Section 8.12-8.14 Chapter 8 Skills (Learning Objectives on Blackboard): 16-18 End-of-Chapter Problems: 55, 77, 79, 88-89, 91, 93-94 These sections bring everything that we have been discussing in both chapter 7 and chapter 8 together. Specifically, these sections lead you through the process of determining the product(s) of a reaction in which we must first determine what reaction is happening before we predict the products. Recognition of the role of the reagent is extremely important – pay very careful attention to Figure 8.25. Two notes on the author’s classification:  CN- is not included. As we have discussed, CN- is a strong nucleophile. It is also a weak base. What category should it be in?  t-butoxide ((CH3)3CO-) is a strong base, but it is very hindered. This makes it is a poor nucleophile. What category should it be in? As an aside, notice that it is the localized lone pair (rather than the delocalized lone pair) that acts as a base when DBN eliminates 2-bromopropane on pg 385. These sections are extremely important, but the most important is probably section 8.13. Figure 8.31 summarizes the decision-making process to determine which reaction will happen. Please do not memorize this – it is much more important that you understand it so that you can make critical decisions. This is high level learning, but you can do it. The explanations and discussions should all be comfortable to you if you have really studied and understood the previous discussions of each individual reaction type (SN2, SN1, E2, E1) –and that individual understanding will enable you to draw the correct products once you have determined the appropriate reaction. Go back and revisit the readings/videos for any reactions that you need to review! There is one video available through the WileyPLUS site that compares and contrasts the mechanisms of all four competing reactions (SN1, SN2, E1, E2) – it is worth a look before reading these sections to remind you about the important features of each reaction type. There are three videos available through the Khan Academy site; the first one helps you determine the role of the reagent and the others walk you through some examples of predicting mechanisms and products. Video Mini-Lecture: Drawing Mechanisms for SN1, SN2, E1, and E2 (6:55) – pairs with section 8.13 Recommended Viewing – WileyPLUS Nucleophilicity and Basicity (12:59) – pairs with section 8.12 Recommended Viewing – Khan Academy SN1 SN2 E1 E2 Reactions: Primary and Tertiary Alkyl Halides (9:10) – pairs with sections 8.13, 8.14 Essential Viewing – Khan Academy SN1 SN2 E1 E2 Reactions: Secondary Alkyl Halides (9:10) – pairs with sections 8.13, 8.14 Essential Viewing – Khan Academy...