Question

3. Propose structures for compounds that fit the following 1H NMR data: a. C.H.Cl2: 8 1.60 (doublet, 3H), 2.15 (multiplet, 2H), 3.72 (triplet, 2H), and 4.27 (multiplet, 1H) b. C.H.Br: 8 1.1 (doublet, 6H), 1.9 (multiplet, 1H), and 3.4 (doublet, 2H) c. CH 40:8 0.9 (triplet, 6H), 1.6 (sextet, 4H), and 2.4 (triplet, 4H) d. CsH1002: 8 1.2 (doublet, 6H), 2.0 (singlet, 3H) and 5.0 (septet, 1H)

Answer 1

calm tay General formula DBE (Double bond Equivalents) 2n+2-m-x 3. (a) Cq H₃ CL O rule 2x4+2-8-2 10-10 This is a saturated compound. S neighbouting carbon hydrogen sumber Ô 1.60 3Hy doublet → CHICH nt & cloublet n+1=2 n=2-1=n=1 2 3.72 2H triplet - сн,сна. nelglouting carbon contains from this obervations, we can propose the possible structure one hydrogen doublet CH₃ CH-CH₂ CH₂ -a otom . multiplet at 4.27 at 1.60 multiplet triplet at 2.15 at 3.72 Hence, dichlorobutane CH₃ CH CH CH 1 1,3-dichlorobutane lo to 2x4 + 2-9-1 O (6) Ca Hg Br DBE This is also saturated compound. 8 1.1 6H - doublet - (CH₂), CH at Q 3.4 2H - doublet & CH₂ CH From this observations, we can propose the possible structure as multiplet at 1.9 CH3 -CH-CH₂ -Br tith doublet doubler at lol 3.4 due to electronegative groBreattachement CH₂-CH-CH₂ Br 1- Bromo-2-methylpropane Hence,

c. GHIO 2x7+ 2-14 DBE - 14+ 2-14 This is has 1 unsaturation. م 0.9 position. 2. 1.6 3. 2.4 GH triplet - 2 CH ₂ CHg (equivalent) 4H sextet 2CH CH₂ CH₂ cequivalent position) 44 triplet 2 CH₂ CH₂ (equivalent position) Focomo these observalech, the possible estructure is at triplet at o.9 ppm en conte é um dirty b + sextet at 1.6 ppm ct triplet at 2.4ppm Hence, CH₂ - CH₂ - CH₂ - C - CH₂ - CH₂ CH3 4-heptatione 2x5+2-10 10+2 10 2 GHIO Og Here also 1 unsaturation is present. S 162 6H doullet (CH ₂ CH or 2 CH CH (at equivalent position) 3H singlet CH C or cryo 14 septet 2.0 5.0 3. (CH₂CH from these observations, the possible structure is doublet at 1.2 TCAI, CH-0-2-czer alight at 2:0 ppm highly septer deshielded proton So, attached with 0 at 5.00pm Hence, CH₂ - CH-0-C-CH₂ CH₂ Isopropyl acetate or Propan-2-yl acetate ethanoate

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