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Unformatted text preview: CHAPTER 7 - Practice Exercises (ORGANIC CHEM I ) ________DR. PAHLAVAN 1. Write a complete reaction for the followings. Please show the stereochemistry of the product and explain why a mixture is formed (if any). a) Dehydration of 3-methyl-3-hexanol in aqueous sulfuric acid b) Treatment of 2-bromo-2-methylbutane with KOH in ethanol c) Treatment of 1,2-dimethylcyclohexene with Cl 2 d) Addition of HCl to 1,2-dimethylcyclohexene e) Reaction of cyclopentene with NBS and water in DMSO 2. Predict the products of the reactions of followings compounds with given reagents. Please indicate regiochemistry when relevant. I) II) III) a) H 2 /Pt b) Br 2 c) HBr d) OsO 4 /NaHSO 3 e) Cl 2 /H 2 O f) KMnO 4 /H 3 O g) Hg(oAc) 2 , H 2 O / NaBH 4 h) O 3 / Zn, H 3 O i) BH 3 ,THF / H 2 O 2 , OH j) CHCl 3 / KOH k) CH 2 I 2 / Zn(Cu) l) Cl 2 / CH 2 Cl 2 3. Describe how to distinguish between the members of the following pairs of compounds by a simple chemical test. For the pair, tell what test to perform, what you expect to observe, and write an equation for each test....
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