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Homework Assignment 1. What carbonyl compound gives cyclohexanol as a product when it is reduced with LiAlH4? 2a. Name the compound below according to IUPAC Nomenclature Rules. 2b. A highly useful and general method for the synthesis of alcohols is the addition of Grignard reagents to carbonyl compounds. Show what Grignard reagants and what carbonyl compounds could be used to prepare the alcohol above. List all possibilities. 3. Why can't the alcohol below be oxidized with CrO3 to a carbonyl compound? 4. Predict the products of the following reactions. Do not show the mechanisms. a. b. c. 5.a. Show 2 ways to synthesize the ether below. Use the Williamson Ether Synthesis and the Alkoxymercuration Synthesis. Show all reagents for each synthesis. b. Which synthesis do you predict would work better for this molecule? You do not have to show the mechanisms or intermediates, but the mechanisms may help you explain your prediction. 6. When 1,2-epoxypropane is treated with sodium ethoxide in ethanol 1-epoxy-2-propanol is the major product while only a trace amount of 2-ethoxy-1-propanol is produced. Show the step by step mechanism using arrows to represent electron flow, and explain these results based on the reaction mechanism. 7. Mustard gas was used in chemical warfare during WWI. Show the mechanism for its synthesis from ethylene oxide (excess) as the only source of carbon. Use arrows to represent electron flow and show the intermediates. Note: SOCl2 is a source of Cl- 8. Which of the molecules below (p-cyanoanilinium ion or anilinium ion) is more acidic? Explain the difference in acidity between p-cyanoanilinium ion (pKa = 1.74) and anilinium ion (pKa = 4.63). Use both resonance structures and words to explain. You may explain in terms of the conjugate amine bases if you wish 9. Rank the following in order of decreasing acidity (#1 = most acidic; #5 = least acidic) Explain your ranking. 10. a. When the imide below is treated with acid, to which atom do you predict the proton will be favored to attach? b. Show the structure of the protonated imide. Include formal charge. c. Explain your prediction. You may draw structures to help explain.

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