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Organic Chemistry Practice Exam & Answers
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EXAM 1 PART II (Chaps. 17,18) PROF. J.I. RIZZO Answer all questions in the book provided to you in SEQUENTIAL ORDER. If you need to skip a question, skip a page. Read each question carefully before attempting to answer it. Only answers written in the answer book will be considered for grading. Solutions must be legible in order for grading consideration. The points possible for each question are indicated, for a total of 80 points for the entire examination. Good luck
explain your solution by identifying corresponding pertinent signals in each spectrum. currentpoint 192837465 C O NH 2
How do you expect the acidity of p -nitrophenol to compare with that of phenol? Draw each structure and explain in words and illustrate schematically your solution. The conjugate base of cyclohexanol is a simple alkoxide ion with the charge localized on oxygen. Further, the two alkyl groups attached through the carbinol carbon atom are electron donating, making the parent cyclohexanol less acidic than is methanol. However, for phenol, the negative charge of the phenoxide ion is delocalized by resonance to the ortho and para carbon sites of the ring, thereby stabilizing the anion and making the phenol a stronger acid. With a nitro group in the para position, there is even greater delocalization of negative charge away from the oxygen and stabilization of the anion, thereby making the p-nitrophenol a stronger acid than phenol.