Question 2 Compound A, C5H10, is reacted with Br₂ in H₂O. The product is then reacted with acetylide anion, C₂H, followe

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Question 2 Compound A C5h10 Is Reacted With Br In H O The Product Is Then Reacted With Acetylide Anion C H Followe 1 (43.36 KiB) Viewed 85 times

Question 2 Compound A, C5H10, 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 BHs followed by NaOH and hydrogen peroxide and finally Jones reagent to give final Compound B, C7H₁4O3. 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 (cm³): 2745 & 1679 CsH10 Compound A 13CNMR (ppm, splitting): 132, s; 119, d; 26, q; 17, q; 13, q 1¹HNMR (ppm): 5.19, 1H, q: 1.64, 6H, s; 1.56, 3H, d 1. Br₂/H₂O 2.:0 3. Lindlar's cat. 4. BH₂ 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