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1.Determine the heat of formation of 2,3-dimethylbutane given the information in Table 7-1 and the data located at http://classes.yale.edu/ chem220a/studyaids/thermo/heats-formation.html. Provide a diagram. 2. Given the information provided in Table 7-1 regarding the heat of hydrogenation of 1-alkenes and data provided at http://classes.yale.edu/ chem220a/studyaids/thermo/heats-formation.html, estimate the heat of formation of 1-octene by two methods. 3. Free radical chlorination of norbornane (see text) can form three monochloro constitutional isomers. Using the usual values for relative reactivity in free radical chlorination, how much of each isomer is formed? One of these constitutional isomers is a mixture of diastereomers. Which one is it? Draw the structure of the two diastereomers. Are they necessarily formed in equal amounts? Of the four possible monochloro compounds, which ones are achiral and which ones are chiral? Of the chiral isomers, will they show an optical rotation? Of the chiral structures, are their enantiomers formed? Explain. Which of the four isomers will produce a norbornene when it reacts with strong base? Explain. 4. Learn how to determine the Degree of Unsaturation of a compound from its formula. We will be using this concept in class. The text uses a formula. I think the website method is easier. Try this one: C16H12BrCl2N3O2S. |
Paul Sabatier (1854-1941) 1912 Co-Nobel Prize in Chemistry for Catalytic Hydrogenation with Metals |
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5. The diagram in section 7-7D (pg. 308) shows that more strain is released in the hydrogenation of cyclobutene than in the hydrogenation of cyclopentene. Using these heats of hydrogenation and the appropriate heats of formation under alkenes [http://classes.yale.edu/chem220a/studyaids/thermo/heats-formation.html#Alkenes], determine the heat of formation of cyclobutene and cyclopentene. What is their difference in their heats of formation? Use a diagram and explain. 6.Alkyl bromide A (C4H9Br) reacts with readily with MeOH to form B (C5H12O). However, when A reacts with MeONa/MeOH, compound C (C4H8) is formed. What are the structures of A-C and how are they formed? 7. Based on the discussion in 7-9C in your text, predict and illustrate the the stereochemistry of the products formed from d,l and meso 3,4-dibromohexane upon treatment with iodide ion. 8. Alkane A undergoes free radical chlorination to give a single monochloro compound B. Upon treatment of B with KOH at 100 oC, no elimination occurs but a new compound C is formed slowly. Compound C reacts with H2SO4 at 150 oC to form D, 2-methyl-2-butene. What are the structures of A-D? Illustrate and explain how they are formed. |