Your initials KE Chemistry 51B - Blum Midterm Exam #1 VERSION A 1-28-15 Submission of this exam means that you agree you are familiar with and have followed the UCI Academic Honesty Policy and course honesty policy (announced on the first day of class and available on the course website), and further, that you have written your own answers and not used aids or copied from another student, or otherwise violated these honesty policies. 1. (18 pts) 5. (7pts) 2. (16 pts) 3._G pts) 4. (3 pts) Total (46 pts)_Your initials 1. (18 pts) For the following set, write in the box a single compound number which correctly completes the statement. 9° a: OH Xou ] Br oy SX 1 2 3 4 5 3 ‘The compound that contains a trans alkene? 3 ¢. The compound that forms an alkyne when treated with NaNEh? Ny ana LS 2 b. The compound that contains an E alkene? 4. The compounds that contain hydroxyl groups? e. The compound that contains a tetrasubstituted alkene? £. The compound that is an ether? (2) The compound that forms a carbocation when dissolved in ethanot? 4 1h, The compounds that form good leaving groups when treated with TsCl and pyridine? I ana 3 i, The compounds that form good leaving groups when treated with POC; and pyridine? \ 3 and J. The compounds that form ethers when treated with NaH followed by CHsBr? and 3 k. The compound that is dehydrated when treated with H2SO,? 1. The compound that undergoes an E2 reaction when treated with sodium methoxide? 4 m, The compound that undergoes an E1 reaction when dissolved in ethanol? 1. The compound that has the best leaving group? ULYour initials 2. (16 pts) Fill in the box with the missing reagent(s) or the major product(s) of the given reaction sequence. If multiple reagents are added in separate steps, provide a numbered sequence the clearly states the order of addition of reagents, If both enantiomers are formed, you do not need to draw both, you may draw only one. Ifonly one enantiomer is formed, draw the correct one. Only answers ‘that are in and fit fully within the provided box will be graded. OH 1. NaH ON Ss om 2 Ag, On a Ne0E 9g Het pies ee ee EtOH oxyYour initials or oy AT 4.2-hydride shit ‘@ carbocation | 1 q ‘nal major product a 'SOGlp, pyridine rl a a he wh | ey Bu atzo Fl coedk ts 4Your initials NaNHa Z 2equiv eo a Hyco ¢ + ATI Sut product ET product | + er ‘one compoundYour initials 3. G@ pts) a. On the below bromocyclohexane chair conformation, place a circle around each hydrogen that is antiperiplanar to the bromine. b. Then draw the major product of an E2 reaction with these reagents, using dashes and wedges to show stereochemistry if present. AY ap leu, 4, (3 pis) Prime time: The chemical reactivity of a class of compounds found naturally in plants, called guaianolides as shown below, was studied as part of an investigation in 2008 into the iological activity of these compounds. Draw the product of the below reaction, being careful to show stereochemistry if present (Journal citation: Tetrahedron 2008, 64, 10996.) | 29Your initials 5. (7 pts) Provide a curved arrow mechanism for the following reaction. Show all steps. Do not combine multiple steps into one step. Only answers that are in and fit fully within the provided box will be graded.Your initials ‘THE FOLLOWING PAGE IS SCRATCH PAPER NOTHING ON THIS PAGE WILL BE GRADEDYour initials THE FOLLOWING PAGE IS SCRATCH PAPER NOTHING ON THIS PAGE WILL BE GRADED