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Unformatted text preview: Name: 1 CHEMISTRY 249S Examination 1 February 8th 2007 Answer all questions in the spaces provided on the examination sheets, indicating clearly what is to be graded. PRINT YOUR NAME AND STUDENT NUMBER CLEARLY ON THE FIRST PAGE OF THE EXAM BOOKLET NAME: STUDENT NUMBER: NMR Spectroscopic Correlation Tables are provided on Pages 9-10 of this booklet. Allowed Aids: Molecular Models Calculators and other electronic devices are not permitted in this examination Credit will be given for partial answers WAIT UNTIL YOU ARE TOLD TO BEGIN Marking Scheme Question 1 20 Question 2 25 Question 3 25 Good Luck! Question 4 60 Total 130 Name: 2 1. ( 20 Points ) Shown below is the chemical structure of 9-tetrahydrocannabinol (THC), the major psychoactive compound isolated from the plant Cannabis sativa . Answer the following questions about the structure of this compound. O H H OH (a) How many chiral centres (sterogenic carbon atoms) are there in this molecule? (b) What is the stereochemical assignment of the alkene? (c) What is the index of hydrogen deficiency (degree of unsaturation) of the molecule? (d) How many distinct methyl group signals would you expect to see in the DEPT NMR?...
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