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Chem 317 - Set 5 extra problems

Chem 317 - Set 5 extra problems - 5 Complete the following...

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d. Which is the stronger base? HO NH 2 or NH 2 f. Amides have a pK b of about 16. At what atom is an amide protonated? e. Which N is most nucleophilic? N g. Guanidine is about as strong a base as hydroxide--why so much stronger than most amines? O (guanidine) NH O Amines 1. Design an experiment using amine basicity to determine if a substituent Z is electron-donating or electron-withdrawing by induction only or by resonance and induction. Describe what you should observe in your experiment for all possibilities of Z. 2. For the following, answer the question and briefly explain: h. Why is this a stronger base (on the carbonyl oxygen) than a regular ketone? a. Which is the stronger base? b. Which is the stronger base? N c. Which is the stronger base? or NH 2 NH 2 H 2 N N H NH 2 O H 2 N NH 2 NH O O or or Et 3 N
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N N HN N NEt 2 O N HN NEt 2 H 3 CO Cl N N CO 2 H NH 3 H H H O O O NH O O a. nicotine LSD b. Br Br atabrine (anti-malarial) c. 4. Order the four indicated protons by decreasing acidity (1 - strongest acid). 3. Order the nitrogens in each by decreasing basicity (1 = strongest base)
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Unformatted text preview: 5. Complete the following reactions: Et 2 NH/H + (- H 2 O) a. Et 2 NH NaCNBH 3 NMe 2 H D b. EtNH 2 /H + (- H 2 O) a. 1. KOH H ? ? NMe 2 H D d. 2. ? ? D 3. NH 2 NH 2 e. ? f ? N N N N O O O O OH O HO O O O O HO HO OH OH OH OH OH OH HO O O N O Br Br I 6. Let's say you brew some Earl Grey tea and get a nice, deep brown, fragrant beverage. The liquid contains, among other things, caffeine ( A ), tannic acid ( B , provides brown color), and linalyl acetate ( C , a terpene which is the principle fragrant component). Your task is to separate these three components and isolate each as a pure, neutral compound. Develop an extraction scheme and indicate which component is where at each step. Be sure to indicate what ionization state, if any, the compounds are in. A caffeine 7. Synthesize the following: B a tannic acid (corilagin) C linalyl acetate I use these as your only sources of carbon a....
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