exams_Blue exam_1 key - 1 Rank the following compounds in...

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1. Rank the following compounds in order of increasing basicity (1 = least basic): N O N 1 2 3 The oxygen is best able to stabilize the negative charge because of its greater electronegativity, so it is the least basic. The compound on the left has several possible resonance structures, whereas the compound in the middle does not. Therefore, the compound on the left is less basic than the one in the middle. 2. Ethynylestradiol (drawn below) is the active component of birth control pills. a. Identify the hybridization of the atoms indicated by the arrows. b. Identify the two most acidic sites in the entire molecule. Mark the most acidic site with the number 1, and the second most acidic site with the number 2. Provide a brief explanation for your ranking. HO HO sp sp3 sp2 sp3 1 2 Explanation: The OH bonds will be the most acidic, because the electronegative oxygen atoms are best able to stabilize the negative charge in the conjugate base. The conjugate base from deprotonation of the OH group on the left is stabilized by several resonance structures, the one on the right is not.
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