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Question 2 Compound A, CsH10, is reacted with Br₂ in H₂O. The product is then reacted with acetylide anion, C₂H, followed by Lindlar's catalyst. The resulting alkene is reacted with BH, followed by NaOH and hydrogen peroxide and finally Jones reagent to give final Compound B, C7H1403. Using the provided spectral data, draw the structure of B and label all provided spectral data. You may show the intermediate products for partial credit. NOTE: Ignore the side reaction that occurs in step 2. You don't know the reaction that would prevent it so I didn't include it. IR (cm³¹); 2745 & 1679 CsH10 Compound A 13CNMR (ppm, splitting): 132, s; 119, d; 26, q: 17, q: 13, q ¹HNMR (ppm): 5.19, 1H, q: 1.64, 6H, s; 1.56, 3H, d 1. Br₂/H₂O 2. =:0 3. Lindlar's cat.. 4. BH3 5.H₂O₂, NaOH 6. Jones reagent C7H1403 Compound B IR (cm-¹): 3200 (broad), 1712 (strong) 13CNMR (ppm, DEPT): 179/none; 77/none; 42/same; 35/invert; 27/same; 8/same ¹HNMR (ppm): 11.8, 1H, s (exchanges w/ D₂O); 4.5, 1H, s (exchanges with D₂O); 2.1, 2H, d; 1.7, 1H, sextet; 1.2, 6H, s; 0.9, 3H, d.
Answer 2 04 For IR (cm-¹): 3200 (broad)- Otstretch 1712 (strong)-stretch 13CNMR (ppm, DEPT): 179/none e 77/none 42/same 35/invertC 27/same 8/samec ¹HNMR (ppm): 11.8, 1H, s (exchanges w/ D₂0 4.5, 1H, s (exchanges with D20) 2.1, 2H, d 1.7, 1H, sextet b 1.2, 6H, SC 0.9, 3H, dC OH a a b но g Lindler' <tones ty zus, Noo t 0