Question

Report: Hydroboration of 1-Methylcyclohexene Mechanism / GC Analysis / Calculations 1. After reviewing the GC and 'H NMR spectra, what is the major product of the reaction? + 3 a. BH: . THF 3 b. 3 H2O2 OH + 3 OH c. NaOH MOH OH racemic racemic major 2. Draw the complete curved arrow mechanism for the reaction to produce the major product, including both the hydroboration and oxidation steps. Repetitive steps need only be shown once. For example, the BH, reacts with 3 alkenes. After showing the first reaction completely you can state "2 x more" and skip to the BR, product. You can use "R" groups to simplify the mechanism if you indicate what the "R" group is. 0.0 H - BHA YBH Bto-oh 3. Draw the structure of the organic species (including stereochemistry) present after each step of the procedure. Do not use "R" groups here; draw the complete structure. After the pH was raised to 8 After the BH, reacted 1 hour After the H2O2 was added BH, B-o-OH

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Answer 1

solution: The structure @ of 2-methylcyclohexanol 1-methyl cyclohexanol The NMR s value of 2-methylcyclohexanol is - CH3 OH a Sa 0.96 ppm (d) for 3H (6 s ł 1. 69 ppm (m) for 14 ① x 3.16 ppm (9) for IH dx 1.2 - 1.8 ppm for 8H. Here the - CH2 Show different splitting pattern - because of prochival and position. proton will axial of Prochinal and axial, equitorial The NMR s value of 1-methylcyclohexanol CH3 a da 1.29 ppm (d) for 34 6 dx 1.3 -1.9 ppm & Show different splitting equitorial position. for 10H . Here the - CH2 pattern nem because of because of proton will and axial, prochiral proc

0 BH 3 & THE ② H2O2, NagH OH I minor) (major) The addition of BH₃. THE in alkene is syn addition of a hydrogen and a hydroxyl group where the double bond had been. The addition of BHz. THE in alkene follow Anti- Markovnikov's rule. The hydrogen atom cittach to more substituted carbon atom and boron attach to less substituted carbo atom, khich on hydrolysis with H2021 NUOM to give major 2-methyl cyclohexanol majo product. Because of all deson's 2-methylcyclohexanol favor over 1-methyl Cyclohexanola xa.