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Homework%2011 - Homework 11 Fall 2009 1 Which of the...

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Homework 11 Fall 2009 1. Which of the following compounds has more basic nitrogen? Explain your choice why one is and the other isn’t. Draw the protonated structures of both compounds and then decide. N N H 2. Which of the nitrogens is most basic. N N H H NH 3. Which nitrogen in nicotine you are expecting to be more basic? Explain your choice. N N CH 3 nicotine 4. a. Protonate the most basic nitrogen in the molecule (draw the structure). b. Explain why the other nitrogen (not protonated one) is less basic. c. Explain why the chosen nitrogen is more basic. N O NH O 5. Determine which nitrogen is more basic and explain both: why it is more basic and why the second one is less basic.
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a. b. N H N H Cl c. NH N H d. N N H H N H N H Assume planarity e. NH 2 MeO NH 2 OMe pKa = 5.29 pKa = 4.20 F 6. Here are few examples of compounds containing nitrogen: N O N O more basic nitrogen less basic nitrogen a. b. N N O H N 1 2 3 1- most basic 3-least basic explain why N NH 2 c. which one would you think is more basic nitrogen and why
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7. a. Protonate the most basic nitrogen in the molecule (draw the structure). b. Explain why the other nitrogen (not protonated one) is less basic.
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