H o h ch 3 o h o h h o 10 puzzles c terpin is a

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H O H CH 3 O H O H H O 10. Puzzles. c. Terpin is a compound that exhibits expectorant properties and is used as a constituent in various cough medications. Starting with R -limonene, propose a synthesis of terpin and indicate the major and minor isomeric products and whether either would rotate polarized light in pure form. OH OH terpin R -limonene Chem 33, Kanan & Stack, 2012, PS 9; pg 7
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11. Provide the step-by-step mechanism for the following transformations. Br HO CH 3 1. NaH, THF 2. H 2 O, H 3 O + OH H 3 C OH Br SMe racemic mixture 1. KO t Bu 2. BH 3 ; H 2 O 2 , - OH 3. TsCl, Et 3 N 4. NaSMe, DMF H When compound A is treated with a strong aqueous HI solution over extended periods of time, 2,3-diiodo-2- methylpropane is isolated. If the reaction is stopped early, several different intermediate products can be isolated, including B and C . Use a detailed, step-by-step mechanism to explain how the starting material gives rise to B and C . O O A H 3 O + / I - OH I B I HO C H 3 O + Chem 33, Kanan & Stack, 2012, PS 9; pg 8
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