Assignment_7_2008 - CHM 1321 Assignment 7 In this...

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CHM 1321 Assignment 7 In this assignment: - Alkene addition reactions - Synthesis 1. Predict the major product(s) of the following reactions and give a mechanism to account for its formation. H 3 PO 4 H 2 O HO H 3 PO 4 H 2 SO 4 + HBr a) b) + HCl c) 1-methylcyclohexene + HCl d) + HBr e) 1-methylcyclopentene f) g) h) + HCl AIBN Δ i) + HBr AIBN Δ 2. When 1, 3-butadiene reacts with HBr, a mixture of 3-bromo-1-butene and 1-bromo-2-butene is obtained. Propose a mechanism to account for this observation. 3. Propose a mechanism to account for the following: OH + H 3 PO 4 H 2 O
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Assignment 7 2 4. Predict the major products of the following transformations: a) b) + BH 3 product from part (a) after treatment with H 2 O 2 and NaOH + BH 3 c) product from part (c) after treatment with H 2 O 2 and NaOH d) e) + BH 3 product from part (e) after treatment with H 2 O 2 and NaOH f) g) 1) BH 3 2) H 2 O 2 , NaOH 5. Show how you could effect the following transformations. Include stereochemistry where appropriate: a) OH b) O c) OH d) Br e) HO O f) OH g) OH
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