Final FS07-Blank - 1. (25 pts) Quick answers: True/False...

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1. (25 pts) Quick answers: True/False questions @ 5 pts each, 3 for the T/F answer, 2 for a counterexample (if the statement is False) or other scratch work for your analysis. a. A compound in which a carbon has four different substituents must be chiral T F b. If a substrate can do an E1 it can always do an S N 1 reaction T F c. All stable isomers of C 3 H 6 O must be polar T F d. Removing electrons always weakens a molecule’s bonds T F e. Aromatic species are always highly volatile T F
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2. (25 pts) Consider the six compounds shown below. A B C D H E H F H Among species A-F , find… (a) (4 pts) An acyclic tetraene _____. (b) (4 pts) Two conformations of the same compound: _____ and _____. (c) (4 pts) The one compound of a different molecular formula _____. (d) (4 pts) Two aromatic compounds that are structural isomers? _____ and _____ (e) (4 pts) The compound with the highest H f value _____. (f) (5 pts) A compound that can undergo Diels-Alder addition with 1,1,1,4,4,4-hexafluoro-2- butyne to form a product with a bicyclo[2.2.2]octa-2,5-diene framework _____.
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3. (25 pts) Consider the three brominated benzenes below. Br Br Br Br Br Br Names:_________________ __________________ _________________ a. (3 pts) In the spaces given, name these compounds, using ortho, meta, para terms. b. (3 pts) All three have similar mass spectra (see next page). The molecular ion portion is blown up above. Write the integer value (no decimal places) of the main (= 100%) ion mass “M” for these compounds (Hint: see the attached table of isotopes): Mass M = ________ c. (5 pts) It turns out that the main molecular ion peak(s) actually show up as a triplet with approximately 1:2:1 peak intensities. Assign integer masses to the peaks drawn above (i.e. label them) and explain the 1:2:1 intensity pattern and mass spacing by identifying the ion formulas, including isotopes, that give the three main mass peaks. d. (5 pts) One mass unit above each of the big peaks, there are little ones, also roughly in 1:2:1 proportions, but only about 6% as large as the big ones. Explain where these come from (i.e. give formulas including isotopes), and how they confirm that it’s a six-carbon compound we’re analyzing. e. (3 pts) The mass spectra don’t help a lot to distinguish among our compounds, so we resort to 1 H NMR spectroscopy. On the next page, add the second Br and the four H’s to each of the bromobenzene structures at left. Then label the H’s A,B,C, etc. to correspond to the labels in the spectra.
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Final FS07-Blank - 1. (25 pts) Quick answers: True/False...

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