01:160:305 Study Guide - Midterm Guide: Wittig Reaction, Lactone, Reagent

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30 Oct 2014
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Practice exam b: in each of the following pairs of carboxylic acids, circle the one that would have a lower pka value and briefly explain your choice for each. (4 pts each; 16 pts total) Periodic table it may be helpful for this problem. 1: looking at a reversible reaction. (a) draw out the overall scheme of (e)-pent-3-en-2-one reacting with ammonia to make. 4-aminopentan-2-one. (4 pts) (b) using information from the following table, determine if product formation will be favored by calculating hrxn. Whatever appears in the box will be graded. 2: cool example of the wittig reaction! The following transformation was reported by patrick murphy and others in 2001. It is an intramolecular wittig reaction between an ylide and a lactone (a cyclic ester) carbonyl. Note that it does form a tetrasubstituted alkene (violating what mcmurry states in his text!). Please draw out the complete mechanism for this transformation. (8 pts)

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