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1、.CHE 230-001 Organic Chemistry Exam 2 (9 total pages including periodic table)- 6 -Cover Sheet! (MAKE UP EXAM)Write your name legibly on the line below._Exam 2, Monday, October 23-Tuesday Oct 24, 2000Name: _ Student ID No:_First: You are allowed to have a writing utensil, a calculator and molecular
2、model set at your seat. Please put away all other materials. Second: Place your student identification on your desk. A proctor will come around to check everyones ID. Is your name and number on your test?Third: Quickly read through the entire exam. Your goal, as always, is to score as many points as
3、 possible. Do not waste time on problems that you cant do if there are easy questions. Fourth: It is critically important that your answers be written in a clear, unambiguous manner. Answers in which your intentions are unclear will not receive credit. SHOW YOUR WORK!Fifth: READ THE INSTRUCTIONS FOR
4、 EACH PROBLEM. answer each question You have until 6:50 to complete this exam. There are no extensions; budget your time.Problem Number Points possible Score1. 10_2. 15_3. 10_4. 15_5.15_6.15_7.10_8. 10_Total 100_1. (10 pts.) Rank the following molecules by their energy of hydrogenation. Label the st
5、arting material of the hydrogenation reaction that has the most negative DG 1, the next most negative DG label 2 etc. An example of a hydrogenation reaction is CH2=CH2 + H2 -> CH3-CH3Put your answers on the line below. A_ B_ C_ D_ E_ F_ 2. When compound 2x below is treated with triethylamine (a b
6、ase) it looses a proton and becomes conjugate base 2y. When 2y is treated with lithium diethylamide (a much stronger conjugate base than triethylamine) 2y looses another proton and becomes conjugate base 2z. a. (5 pts) Draw the structure of 2y and label it. b. (5 pts) Draw the structure of 2z and la
7、bel itc. (5 pts) Explain your answer, why is one site easier to deprotonate?_3. (10 pts) Provide IUPAC names for the following compounds. Use E,Z nomenclature when necessary. (a. 3 pts.) (b. 4 pts.)(c. 3 pts.) a. _b. _c. _4a. (10 pts.)Use an energy diagram and very few words to explain why cyclohexa
8、ne does not attained the boat conformation when it ring flips 4b. (05 pts.)What structure does cyclohexane pass through during ring flipping? _5a (5 pts.) A model might come in handy for this problem. Consider methylcyclopentane. Draw the conformer of lowest energy. 5b (10 pts.) Explain your answer
9、in 5a. Why did you choose the conformation that you drew? What is (are) the major factor(s) affecting the conformation of methylcyclopentane? A very short answer could be enough._6. (15 pts.)Answer the question based on the following facts. The pKa of cyclohexylamine is 42. Find the pKa of toluene i
10、f a 1:1 mixture of the conjugate base of cyclohexylamine and toluene equilibrate with an equilibrium constant K = 10.0Work space below. Show your work for partial credit. The hydrogen atoms shown are lost in the deprotonation reactions to which the pKa values refer. 7. Consider the two transformatio
11、ns below. 7a. (5pts.) Which tranformation has the most favorable DG as written? ANSWER: _ (which reaction has the least positive DG)7b. (5 pts) Explain your answer above. What is the major factor making these two transformations different energetically? Give a very short answer!_8. (10 pts) Calculate the ring strain in cyclooctane given the following information. Remember that there is no ring strain in cyclohexane. :