Assignment _5 - Chem 3600 Homework assignment #5 (Chapter...

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Unformatted text preview: Chem 3600 Homework assignment #5 (Chapter 18) Due Date: Wednesday, 04/14/2010 The following problems in Chapter 18 of the textbook are also required: 3-5, 14, 17-20, 24, 26-31, 36-3 8, 41, 43, 50, 53, 55, 57, 60, 62, 65, 69, 70, 73, 78, 80, 81, 83, 85. You do not need to turn them in, however 1. For each group of compounds, List them in the order of decreasing acidity of the oc-H. (a) Acetone, acetaldehyde, ethyl acetate, N,N-dimethy1 acetamide. o o o o o o O O (b) M HM WK Meo’u\(U\ H H H H O O O (c) RJOH R\/U\Br RQLT/ 2. List the following compounds in the order of reactivity in decarboxylation reactions: MeOMO- AHLO— MO- 0 N02 0 3. Provide a plausible mechanism for each of the following reactions: (3) o o 0 0 0 8 Lb K2C03, heat W + + I ——'—> «:«5» (b) o Me\+,Me (Z O S NaH . + /S~ Me ————> intermediate —————> Me Me 4. Give the product of the following reactions: 0 o 0 Hi Br2 t-Buo' )k/CN HCl, H20 ___.> ——~> ————> -——> O HO " heat 0 O 1. MeO_ add slowly O A )L ’ 1. LDA, -78°C + OMe 2 HCl _———> add slowly excess ‘ 2. Mel o o — o /u\/\/U\ —HO—> f H0— H + ——-> dilute o o O 5. The following is a synthesis of longifolene by El. Corey and coworkers published in 1951. 0 0 0’5 0/3 0/» Me 1 2 O 3 O 4 O ———* ———-> -——-> ____>Me O O O / OH Me OH 5 l TsCl, Pyridine Me O 8 O 7 ‘ 0/9 6 0/03 NEt3, heat HCl KZCO3, MeOH ‘— O 0 Me OH Me Me Me OTs 9 NaH, heat then Mel Me M60 Me Me 11 Me Me 10 £5 HZNNHZ, KOH, heat @ £> ————> Me Me Me longifolene (a) Provide the reagents and conditions needed for step 1, 2, 3, 4, and 11. (b) Explain the regio-selectivity in step 2, step 4, and step 9. (0) Step 6 is one of the difficult steps to understand. Propose a reasonable mechanism for it. Hint: The mechanism is similar to Pinacol rearrangement: htm://en.wikipedia.orgzwiki/Pinacol_rearrangement (d) Give the curved arrow mechanism for Step 8. 6. The following transformations require no more than 5 steps (excluding quenching or neutralizing steps with water, acid, or base). You can use any reagents you need. 0 0k Me P Ph —> \g/\Me __, Ph h Ph Me EtO OEt HO ...
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Assignment _5 - Chem 3600 Homework assignment #5 (Chapter...

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