sampexam2 - boiling point and which has the lowest Hexane...

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350 Organic Chemistry Sample Exam Spring 2011 TR 2:10, Prof. Bartmess - This is about 2/3 of what you may expect on the "hour" exam. This does not cover all possible topics ; it is intended as a guide to the general types of questions that I might ask, and how I tend to state these. I will leave room on the real exam for your answers. There will be one of these before the first hour exam, but not before the later exams. On the hour exam, I will tell you: -Please think your answers through before committing them to paper. -Be legible; if I can't read it, it's wrong. -Don't put answers on the back of pages; such material will not be graded. 1. Give the names of the odd-numbered normal alkanes smaller than C10, in order. 2. Give substitutive names for the following compounds: a. (CH 3 ) 2 CHCH 2 CHCH 2 CH 2 CHCH 2 CH 2 CH 3 CH 2 CH 3 C(CH 3 ) 3 b. OH CH 3 CH 2 CHCH 2 CHCH 2 CH 2 CH 3 CH 2 CH 3 3. For structure (a) in 2., how many primary carbons are there? Secondary? Tertiary? Quaternary? 4. For the following series, indicate which of the three has the highest
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Unformatted text preview: boiling point, and which has the lowest: Hexane, 2,2-dimethylpropane, pentane 5. Label the carbons, oxygens, and nitrogens in the following molecules with their hybridization state. H-C≡N CH 3 OCH 2 CH=CH 2 HC≡C-CH 2 CH=CH 2 6. Draw 3-ethylpentane, using a Newman projection, to show its conformations about the C2-C3 bond. Show all staggered and eclipsed forms. Which is the highest energy eclipsed conformation? Which is the lowest energy staggered conformation? 7. Circle the side of the following reactions that are favored (= higher concentration) at equilibrium. HS-+ H 2 O 5 HO-+ H 2 S 8. Fill in the missing reactant(s), reagent(s) or product(s) for the following reactions: PBr 3 P Me 2 CHCH 2 CH 2 Br tBuOH 5 tBuI 9. Draw a complete "arrow-pushing" mechanism, including all intermediates, for the following reaction: HCl CH 3 CH 2 CH 2 CH 2 OH → CH 3 CH 2 CH 2 CH 2 Cl...
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