CHMB41H3 Study Guide - Midterm Guide: Trigonal Pyramidal Molecular Geometry, Newman Projection, Cyclopentadiene

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26 Oct 2013
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Part i (10 marks) - multiple choice (1 mark each) place your answers in the boxes on the answer sheet: the structure of doxorubicin, a drug widely used in chemotherapy and treatment of cancer, is shown below. Answer questions 7 to 9 using one of the following 6 terms. (a) constitutional isomers (d) enantiomers (b) identical molecules (e) not related (different) (c) cis/trans or e/z isomers. Br: which is the correct iupac name for the structure shown on the right, 5-sec-butyl-4-cyclopropyl-7-methylnonane, 5-sec-butyl-6-cyclopropyl-3-methylnonane, 4-sec-butyl-5-cyclopropyl-2-ethyloctane, 5-sec-butyl-4-cyclopropyl-7-ethyloctane, 5-sec-butyl-7-ethyl-3-methylcyclopropane. 1- bromo-4-sec-butylcyclohexane. (iii) designate which conformation (a or b) is more stable in both part (i) and (ii). (circle one for each on the answer sheet). Explain your choice for each answer (maximum 10 words): (10 marks) (i) draw the equilibrium reaction between cyclopentane and ho-. The pka of water is 15. 7 and pka of cyclopentane is 50; will cyclopentane be deprotonated by the hydroxide anion? (ii) draw the equilibrium reaction between cyclopentadiene and ho-.

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