Question

6. (2 pts) A student reacted an alkene, C4Hs, with mercuric acetate in water followed by sodium borohydride to make product 1. Then product I was further reacted under Jones conditions to give product 2. After purification, product 2 was reacted with methylmagnesium bromide in ether followed by an acidic work-up to give product 3. Shown at the left is the "H-NMR of product 3, which also showed a major, broad IR absorption at 3300 - 3400 cm Draw the structure of product 3 in the box below ill

Answer 1

Answer: Analisise of NMR & IR. I IR - for 3300 - 34,00cm. This ar streening all. frequency is o-1 3300 3400 cm. peot H NMR, The NMR shows following analysis. 1. 0.8 s a triplet 34. 2 1.2 & singlet 64 3. 1.45 singlet in 4 1.7s quorate zu 0.85 triplet 34 H₂ - CH2 34 triplet 2. 1.28 singlet 64 AH 1. 28 64 singlet

3. 145 singlet in oru 146 singlet quortate an. 4. 1.78 CH₂ - CH2 lifs combining quertate all fragment we get structure. By CH3 2 singlet CH₂ - CH₂ - 6-CH3 TON triplet quertute singlet By reaction scheme K2C6707 HgcOAc) Napuh H2804 Acetore H₂ mg Br HO OM product. The first stef is reaction step is liol formation, second oxidation 3rd step is Goignard to gives poulet.