Question

the first two questions are asking to do acid-catalyzed mechanism. the last one is mutliple choice question

yl-Fall 2019 SO. Draw the mechanism for the acid-catalyzed hydration of 3.3-dimethy the final product in the box below In words: protonation water gives a pro rearrangement to a more stable tertiary carbocation. Then (1) capture deprotonation gives the major organic product. Four curved arrows total on of 3,3-dimethylcyclohexene. (Draw the intermediates in the blank bra otonation of the alkene gives a secondary carbocation that hd on. Then, (10) capture of water gives a protonated alcohol (oxonium ion ankets tin) unders non), lastly. HO: 1,2-methide shift +[H]/ 2 carbocation 3 carbocation -TH") + H,O" (iv) protonated alcohol major organic product 31. Examine the hydroboration-oxidation product of (R)-Limonene drawn below. (1R 2R,5R)-5-Isopropyl-2-methyl-1-cyclohexanol Draw the more stable chair-conformation of this product (ie lowest in energy). Be sure to clearly draw accurate axial and equatorial positions on the correct enantiomer. (Hint: number your cyclohexanering) Redraw in most stabil chair conformation 1) BH, 2) NaOH/H.O HO (R)-Limonene (1R 2R,5R)-5-Isopropyl-2-methy-1-cyclohexancl most stable chair conformation 32. In W. S. Johnson's elegant synthesis of the pregnane steroid sex hormone, progesterone, identify the missing ozonolysis reaction product [?] of the starting tetrasubstituted, cyclic alkene. ch CK он н ун 5% KOH 10-05 -70°C in CH CI/CH,OH - C HO AE -15 to 23 "C JACS, 1973., 4416 NH Progesterone (sex hormone) Icketaldehyde [d] dialdehyde [e] molozonide (a) diketone [b] 3 alcohol 12

Answer 1

Mechanism mer Ho-sol bronne (87 1,2-methyl - sur shikt (ii) the Ching lesson 4G HO2S002 Civ 1504 Poolcoated alcohol 31) Answer more stable chais com sur mahoon i) Bih OH i Nauhthor 32) Answer + 54. KOH S 1) 02-8c e4 2012/ 04 11) Zn (ACOH - 15 to-23C Answer [a] dikelone