W03 problems3a key

W03 problems3a key - Problem Set III a(2E-2-hexen-5-yne...

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Problem Set III 1. Draw the structure for each of the compounds given below. a) (2 E )-2-hexen-5-yne b) 5-bromo-1-pentyne 2. Draw all possible products for the transformations below. a) Winter 2003 b) c) d) Alkynes (Page 1) HBr (excess) e) f) g) H 3 CC H 3 H 3 H 3 Br 2 (excess) H 3 H 3 H 3 H 3 HgSO 4 / H 2 SO 4 H 3 H 3 H 2 / Pd H 3 H 3 H 2 / Pd / CaCO 3 H 3 H 3 Na / NH 3 h) H 3 CH 1. NaNH 2 2. CH 3 2 Br i) H 2 / Pd H H 3 O + Br Br Br Br O O H 3 C
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OH Ph Br O O OH OH H O H O H O H H 1. Na / NH 3 HH HgSO 4 H 2 SO 4 H 2 / Pd CaCO 3 HO OH NaNH 2 2. Br 2 H O PCC OH NaNH 2 HC H 3 NaNH 2 Br H 3 NH 3 Br CH 3 H H Problem Set III (Answers) 5. Propose a synthetic route for each of the following molecules starting with an alkane, alkene, or alkyne of 3 carbons or less.
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W03 problems3a key - Problem Set III a(2E-2-hexen-5-yne...

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