Question

Chemistry 2401 Experiment 7 Acid Catalyzed Dehydration of 3.3-Dimethyl-2-Butanol with Rearrangement Experiment 7 Pre-lab Assignment Dehydration of 3,3-Dimethyl-2-Butanol 1. Draw the structures of all the expected products from the following reactions: a) 3-methyl-3-pentanol + H = b)2-methylcyclohexanol + H - c) 2-methyl-2-butanol + H - d) 2,2-dimethylcyclohexanol + H = This reaction will give a complex mixture of products, since rearrangements can occur. Show the full mechanism for this reaction and how the possible products can form from the carbocation stage.

Answer 1

x + = + 90+ (11,40+) product Nolelt To anter Yes, que you have to see the (1) L + 2 + 140*H* 2-hydrogen of the next ОН Соль оn оf carburaton) = W +420 ++ (e) 10+ H ca t + = c + 10+ H+ Mechanism 12- meloup I-HO HO 2°-contocation 1 1,2-hydride stift

alkene fermed wifth reaargemant other alkent Same These are the other alkenes formed / found along with 3. We know the density of 3,3-dimethyl-2-butanal f = 0.812 glome orglaan #okom = Vx8 = 3mL x 0.812 g/ml = 2:436 g Molecular mess of 3,3-Dimethyl-2-butanol = 102.17 glimot (MW) # of moles = m = 2.436g somet MW 102.17 glmol - 0.0239 mol = 23.9 mmol = 2.39x10 mot I mol of 3,3-Dimethyl-2-but and gives 1 mol of butene. So, #of moles of butene - 2.39x10-2 mol Molecular mess of butene = 102 g/mol -18 eg mot seg Hence, theoretical yield mass of bulene formed - 200 2.398 10 2 x 84g loool of butene=2.01 g v2.09 = 2.01 g